My Cheating Girlfriend Tries Anal

(This story is Part 4 of a series pertaining to my cheating college girlfriend. Although it references previous events it can be read as a stand alone story)

Christmas break had arrived and Kate hopped on a plane to come and spend the holidays with me and my family. I was so excited that I finally got to have sex again and Kate was excited that she got to have sex again without feeling guilty afterwards for cheating. When she walked through security I ran up to her and gave her a big hug. We kissed and held one another for a minute before driving back home.

It felt amazing to be in her presence again. We caught up with everything going on in each other's lives (well almost everything). How her classes were and what friends she had made. How my work was going. When we got back to my place we went straight to my room. Kate was ferocious. She ripped off my shirt and dug her nails into my back. Never had I seen her so passionate. My cock instantly swelled with blood and within a minute we were naked and fucking on my bed. She told me to get on top of her and fuck her hard. I thrusted harder and faster but she just kept saying harder and harder. I couldn't keep such a fast pace and last that long, plus it had been months since I'd had sex, so I came after a few minutes, shooting my load on her flat, toned stomach.

Kate reached forward and gathered some cum on her fingers before sucking them clean while locking eyes with me. I couldn't believe it. Kate was like a whole new woman in bed. I figured her female friends must had talked about their sex lives and opened her mind to new things. I knew her female roommates slept around a lot so it made sense to me that they probably told her a thing or two.

The rest of our time together was euphoric. We had sex every morning, slept in late, went to restaurants, and saw some friends. Soon the break was over however and there was still one milestone I was hoping to achieve with her. Anal. Something she had been hesitant to do in the past, but before she had hated cum and now she was eating mine so I thought it was worth it to give it a try on our last night. After fucking in doggy position, I pulled out my cock and rubbed it on her asshole.

"I'm not ready for that yet, babe," she said.

"Ok."

We continued with sex, fell asleep and then she left back home in the morning. Kate had been back for three weeks when her horniness from a lack of sex starting getting the best of her again. She thought of texting Ryan, and feeling his length fuck her deep again. She thought of knocking on her roommate David's door, and feeling his girth stretch her tight pussy to the point of orgasm like before. She even thought of texting Justin from the Halloween party; she loved the way he railed her hard during the party. But ultimately she chose to grab her vibrator and send videos to me. Our time together had been great and the sex was good so she decided to abstain from meeting any guys.

Two weeks later Kate, her roommate Jessica, and a few other friends decided to go out to the club for a girls night. They got all dressed up. Kate wore a black tube top showing off her tan, tight stomach with black leather pants that hugged under her ass perfectly. In those pants she turned heads everywhere she went. They all pre drank hard and then arrived at the club, dancing and taking shots throughout the night. On the dancefloor Kate tried to alleviate her desire for sex by grinding on different guys. She rubbed her ass over their cocks and flirtatiously brought her lips close to theirs before pulling away and dancing some more. It didn't alleviate any of her craving for sex but it was fun for her so she continued.

At one point Jessica said her friend Connor, the manager, would let them into the VIP room with them if they wanted, where they could get free drinks too. All the girls went to the VIP room.

Jessica's friend, Connor, welcomed them with a line of shots as they sat around a few couches and had some drinks. The room was private from the rest of the club, so they were able to have a fun time amongst themselves mingling with Connor and some of his other friends. After some time talking Connor pulled out a joint and offered it to the group. They passed the joint around and eventually to Kate.

Kate rarely smoked weed. She had at some concerts and occasionally with friends but generally stayed away from it. Tonight however, she decided to go for it since they were having a good time. The weed hit her hard and before she knew it she was sitting on the couch, relaxed, and enjoying the high. The group decided they wanted to go back out to the dance floor for a bit but Kate felt too high and wanted to stay back. Connor's friends left with the girls, playfully grabbing at their hips and asses as they all laughed and made their way to dance with each other. Connor stayed behind too, not being able to join them on the dance floor as a manager on shift. For a moment Kate felt jealous; she wanted to keep dancing on guys. But then she and Connor started talking more.

They chatted on the couches for a little while. Had some typical "deep" conversations while high, and laughed non-stop. Kate couldn't help but keep noticing how attractive he was. Connor was just over six feet tall and his frame was stocky, like the build of a rugby player. He actually had been a really good wrestler back in high school. He was charming and she found herself daydreaming of him fucking her. At one point Kate started to feel a body high; she was very aware of the leather on her skin and her body in space.

"My pants feel so weird on my legs" she laughed, standing up and turning around. Connor got a glimpse of her ass and could hardly believe how firm it pressed against her pants.

"I don't mean to be too forward but your ass looks incredible in those pants."

"That's so nice of you to say!" she said, blushing. She sat back down on the same couch as Connor. He slid closer to her.

"Have you ever had sex while high?" he asked.

"Not yet," she replied.

Connor reached over and grabbed her face. He kissed her with his open mouth, their tongues in each other's mouths. Connor's hand began to find its way around Kate's waist, then up to her breasts. He kissed her neck as he held her tightly, slowly going lower until he reached her breast. After pulling off her top he sucked her nipples gently; a wave of energy pulsed from Kate's nipples down to her clit. She felt incredibly aroused and the weed was amplifying every feeling in her body.

Connor unbuttoned her leather pants, pulled them down over her ass before kissing it gently and smacking it a few times. He cupped under her perky, firm cheeks before taking off her pants and thong completely. Kate lay back on the couch with her legs spread apart as Connor buried his head between her thighs. His tongue caressed up and down her pussy before he licked her clit in firm, hard circles.

"Just like that," Kate moaned.

Connor continued on, Kate squirmed, ready to orgasm, before her body shuddered as she writhed on his tongue. As her body relaxed again Connor slowly made his way further down, and began slowly licking her asshole. Kate was surprised by the initial feel of his tongue. Her body twitched in response and she wanted Connor to continue.

"Yes, yes, yes" her mouth contorted to say, almost involuntarily from how good his tongue felt on her asshole.

Connor kept going before putting one finger in Kate's ass while simultaneously licking her clit. Kate had never had anything in her ass before and the feeling, combined with Connor's tongue, and the weed brought her over the edge immediately. Kate came, for a second time.

Connor pulled back and began undressing. He pulled down his boxers to reveal a semi-hard, long cock dangling by his leg. Kate licked the head of his cock, before slowly taking it in her mouth while looking up at him. She moved her mouth up and down over his cock, spit running from mouth while doing so. His cock grew more rigid, somehow still growing longer in the process. She took Connor as deep as she could, but left a few inches remaining, his cock too long for her petite frame and mouth.

Connor grabbed Kate by her waist and picked her up, repositioning her on the couch with her ass back to him and her arms on the armrests. Connor slapped his cock gently against Kate's ass before rubbing the head of his cock up and down her pussy. She was dripping wet in anticipation. His cock slipped through the lips of her pussy and disappeared inside of her. He pulled her hips back and began clapping against her ass. Kate jumbled out moans of pleasure and his cock slid in and out, deep and hard over and over again.

Connor pulled his cock out and started rubbing it against her pussy some more. His cock rubbed up and up, until it reached her asshole. The head of his cock gently rubbed against her tight, pink, virgin asshole. She gripped the couch harder. His cock began to push against her hole, before breaking through and sliding in slowly.

Kate gasped in delight.

"Nice and easy" said Connor, as he gently pushed his cock in and out of her asshole, taking it slightly deeper with each successive thrust.

5". 6". 7".

"That's too deep! I can't take you that far," she said.

"Once you go deeper, it feels better I promise," he said.

8". 9". 10".

Another gasp in delight.

"See," he said.

Connor continued fucking Kate in her ass, building up more power and more speed as she got used to his cock. His hands firmly gripped over her ass cheeks as he thrusted forward while she dropped her hips back on him.

"I'm close," he groaned.

Kate pulled forward off of Connor's cock. She turned around and knelt below him, took his cock in her hand and placed her lips around it. She began jerking his shaft while sucking the head of his cock and moaning in delight. Connor shuddered out as he shot his load into the back of her throat.

Kate smiled as his cum spurted into her mouth. She sucked the last drop out before proudly opening her mouth to him, showing him his cum before swallowing it down.

Then the doorknob rattled. Someone tried banging on the door.

"Hello! Kate? Connor? It's us, let us in!"

Kate and Connor gathered up their clothes quickly. She fixed her hair while he straightened out the room. Connor opened the door and the whole group came flooding back in from the dancefloor. They grabbed some more drinks and joined Kate and Connor on the couches.

The timing had been perfect. They stayed and hung out in the VIP room until the end of the night before some people started heading home. Jessica, her roommate, told Kate she would have to take an Uber back alone because she was going back with one of Connor's friends. Jessica too had a boyfriend, but after seeing and hearing Kate have what sounded like the best night of her life with Ryan last semester she felt inspired to fuck another guy like Kate (she was unaware that Kate had slept with Justin, David, and now most recently Connor, too).

When Kate arrived at her house the Uber driver got out and walked around the car, opening the door for her. Kate stepped out. The driver saw her taut ass in her leather pants and couldn't help but stare.

"I don't mean to be rude, but your ass looks fine as hell" he flirted.

"The last guy who complimented my ass had a pretty good night" she responded.

"He's a lucky guy. I hope I'm lucky too."

She laughed. "A squeeze wouldn't hurt I suppose" she said flirting back.

He stretched his hand over her left cheek and gave a solid squeeze, then jiggled her ass a bit and rubbed it firmly.

"Goodnight" she said, and seductively walked back into the house, her ass swaying back and forth.

She thought about the fact that she had just let a complete stranger grab and jiggle her ass.

"What am I doing!" she thought, as she walked through the front door.

She couldn't fight her urges. Her sex drive was at it's peak and there were so many potential suitors always at her door, ready to fuck her brains out at a moment's notice. And then there was me. I was hours away and we fucked, but not brains out fucking. David's girth and Connor's length had been able to hit new places and give her new sensations she never even knew about. It seemed impossible to stay faithful to me.

She brushed her teeth, removing the taste of Connor's cock and cum that was still in her mouth. She texted me saying she had a good night with the girls and that we should FaceTime soon.