A New Life Pt. 01

Last night, my life changed completely. Last night was my first date with the love of my life, Anita.

Anita and I met recently at our very small local college; both of us being employees at the college bookstore. I remember being stunned the very first time I met her. With her curly dark hair, olive skin, 36DD breasts and fit figure, it was clear that any man who caught a glimpse of her couldn't help but stare. She exuded sex appeal even without trying, which resulted in numerous rumours about her previous relationships and her extra-curricular activities with her male professors.

I, on the other hand, was lanky and short compared to the rest of the guys in my year. While I wasn't particularly bad looking, I had very feminine features. Furthermore, unlike Anita, who I assumed had slept with multiple partners, I had only recently lost my virginity. Embarrassingly enough, the only person I had ever fucked was my bully, Jason, while crossdressing as my sister. A detail I was certainly going to hide from everyone else around me; especially Anita. I had just started dating her and I didn't want to ruin that anytime soon.

Tonight, as we finished restocking the store, I decided that now would be the best time to get to know her, as we were completely alone.

"Hey, Anita! You wanna hang out and talk?" I asked her, hoping that she would still give me the time of day.

"Sure thing, Joshua! What do you have on your mind?" she asked, sitting down on a box next to me. Immediately, my mind jumped to the numerous rumours I had heard about her relationships with her professors and her previous boyfriends. I tried to sweep the thought out of my mind, knowing it would only hurt me to hear about her sexual encounters with other men, but I couldn't shunt my curiosity.

"I don't know... I've heard a whole bunch of rumours about you and I was just wondering if they were true..." I fumbled. Her cheeks turned red and I could tell that I had hit a sore subject with her.

I immediately tried to deflect the conversation but she responded, "Don't worry, I don't mind answering. It's just super embarrassing to be known for things that I haven't even done. Most of those rumours aren't even true. I've never slept with a professor, that's just something that guys spread about me because I get high grades. To be honest, I have only had sex with one guy and I completely regret it."

I could tell that she was being sincere, but she had said that "most" of the rumours had been false, which implied that some of them were true. As though she read my mind, she said, "If you really want to know, I can tell you about what happened, but I won't tell you the guy's name and you have to promise you won't judge."

"Sure thing! I would never judge you," I said, knowing that I would regret it in the end but I had to know the truth.

She told me that it had all started in their final year of high school. Anita was clearly the hottest girl in their entire school, but due to her orthodox raising, she was still a virgin and had never even dated anyone. It was this fact that made her even more attractive to all the boys. It was one day after school when her ex-boyfriend, who she called Jason, came to talk to her.

Anita had heard rumours about how Jason was planning on asking her out, but she was caught off guard when he actually approached her. She had heard all about how he played with girls but she couldn't help but fawn over him. Not only was he one of the smartest students in the school, he was also, by consensus amongst the girls, the hottest guy by far.

"Hey Anita, you mind if I talk with you privately?", he said. As he spoke, she could feel her heartbeat rising and she could hear the sex appeal drip off each word. She knew that her parents wouldn't approve of her dating, nonetheless dating someone who was African-American but listening to him couldn't hurt.

"Sure thing!" she said, trying not to sound too excited. He led her into the farthest stairwell in the school and looked at her with his dark, piercing eyes.

"So, I heard that it's finally your eighteenth birthday! It's about time you joined us adults in the real world. I was just wondering if you wanted to come to a party that I'm holding today at my place? My parents are gone for the weekend. So what do you say?"

Anita couldn't help but say, "Yes!!", as quickly as she could.

"Great! I'll see you at 8 at my place. Oh, I'm not inviting some of the guys, so try to keep this between us, I wouldn't want them feeling left out." he said with a wink as he left. Anita stood there taking in exactly what had happened and then rushed to her best friend Vanessa's to get ready for the party. She called her parents and told them that she was going to be studying late at Vanessa's, knowing that her parents would never let her leave the house otherwise. When she got to Vanessa's place, she told her all about what had happened.

"So what do you think?" Anita asked her after explaining everything. Vanessa had dated Jason for a really short period of time, but they broke up quickly, although they had stayed friends.

"He's great! You guys would be perfect together! He's smart, charming and he knows how to treat women," she told her. She then giggled a little and added, "Plus, it's true what they say about black guys." She could see the confusion on Anita's face so she just shrugged it off saying, "Don't worry, it'll be fine. Here, wear my black dress and let's go have fun!".

Anita put on her black dress and stepped out. "You look amazing!!" Vanessa exclaimed, "You just need a touch of make-up, trust me, I know what Jason likes." She spent the next couple minutes putting on a little mascara and a dark red/maroon-ish lipstick. Anita looked in the mirror and even she was shocked by how good she looked.

The dress hugged every inch of her body and exposed her legs, leaving little room for imagination and her lipstick made her look sultry. The only issue, that Vanessa was quick to point out, was that her panty lines were extremely visible. "Do you have a thong?" Vanessa asked her. Obviously, Anita had never even owned a thong because her parents found them to be too provocative. "I know this is going to be a bit awkward, but it'd look a lot better if you just didn't wear any panties..." Anita felt hesitant but Vanessa quickly reassured her, "I mean, it's not like people are going to be on the floor looking up your skirt." After they both got ready, they walked over to Jason's place.

When they got to his place and rang the door bell, Jason opened the door wearing nothing but boxers. Anita's jaw dropped as her eyes drifted down his chiseled ebony abs and onto the thick bulge in his boxers. It quickly occurred to her what Vanessa had been giggling about earlier. "Sorry... were you...uh... getting ready? I guess.. we're early..." Anita stuttered hoping that he wouldn't notice her shock. He chuckled and said, "Something like that... Something came up, come on in, I'll explain it in the living room." Anita and Vanessa walked inside and found the house completely empty except for Jason.

"Vanessa, do you mind grabbing us drinks, while Anita and I talk?" he said.

"Sure thing!" Vanessa said, as she winked at Anita and walked into the kitchen. She must've come here before, as she seemed to navigate around the house with ease.

"I see Vanessa's dressed you up just as I like," Jason said, sitting down beside Anita. "I've had my eye on you for a while now." He slowly put his hand on her leg and slid it up her dress. She saw the bulge in his pants grow and she could feel herself getting wetter with each passing moment. She gasped as his fingers touched her moist pussy. "Stop," she barely gasped. "It doesn't look like you want me to stop," he said as he pushed in deeper. Her body was betraying her but she finally pulled the strength to push his hand away and stand up. She told him she was leaving and Vanessa walked into the room asking what was wrong.

"Nothing, we're just leaving now. I'll explain on the way home." Anita told her.

"Actually, Vanessa's going to stay here with me, aren't you?" Jason said, staring straight at Anita.

Vanessa looked at Jason with lust in her eyes and said, "Yes Master, whatever makes you happy." Anita couldn't believe what she was hearing.

"Show Anita why you're both here today," he said. Without any more instruction, Vanessa dropped to her knees and pulled down his boxers. By now, his cock had grown to it's full size of at least 9 inches. She opened her mouth and started to suck it, moaning as she did. It was clear that she had practice, as she took the entire thing down her throat without any effort.

Jason looked at Anita with a smirk and said, "See, because you couldn't take what was yours, I guess Vanessa'll have to do the job." Anita could feel a sting of betrayal as she watched her friend succumb to him, but she realized that she wasn't upset that Vanessa had chosen him over her... She was upset that Vanessa was the one to please Jason.

"See the thing is, Vanessa's been my personal little slut for the past few years. Anytime I see a girl that I want to fuck, I get Vanessa to become friends with them and convince them that I'm a great guy. She then gets them dressed how I like and brings them over to my place for some fun." he said, clearly proud of himself. "Right now, I could pretty much call any girl in our class and they'd come over in a heartbeat and do exactly what Vanessa's doing. If you wanna leave, go ahead, you're the one missing out."

Anita stood there unable to make herself leave the house. "Slut, it seems like Anita is having a bit of trouble, why don't you help her out?" Jason said to her, giving her a slap on her ass as he took a seat on the couch.

"Yes, master," she said as she walked over to Anita. She led Anita directly in front of Jason and placed her hands on Anita's hips, pulling her closer. "Come on, it'll be fun, I know you'll love it," she whispered in Anita's ear, "Let me help you with this." Vanessa undid her own clothes, leaving her completely naked. She then proceeded to take off Anita's clothes. Vanessa gave her a kiss and slowly began to kiss her neck, making her way down to Anita's dripping pussy. Anita let out a soft moan as she felt Vanessa eating her out. Anita looked at Jason and she felt complete contempt for making her feel this way but as she looked at him stroking his cock on the couch, she couldn't help but crave it.

"Slut, stop now, let's see if she's willing to work with us now." Vanessa immediately got up and sat with him on the couch, starting to make out with him. Anita felt herself, against her better judgment, drop onto the floor and crawl towards him. She opened her mouth, as he gripped the back of her head and pushed his thick, black cock into her mouth. She felt herself gag and tear up as he pushed it deep down her throat, but she felt determined to make him happy. She couldn't explain why, but she craved his approval. He began to fuck her mouth slowly and she could taste his cum leaking out with every thrust. She realized that at some point, he had stopped trying and that she was the one bobbing up and down, trying to make him happy.

"Now, stop, get on the couch and spread your legs," he said to her. She instinctively got up and sat on the couch with her legs open. Vanessa stood at the side, watching as Jason placed his cock near Anita's pussy.

"Aren't you going to wear a condom?" Anita asked him.

He slapped her ass hard, telling her, "From now on, you address me as 'Master' and you never question anything I say or do. Condoms are for wimps, I ain't gonna fuck you unless you crave my dick. So, do you crave my dick?"

Anita had been raised to be strong and to stand up for herself, but at this moment, she forgot all of that. She only wanted to please Jason. "Yes, please Master, fuck my tight white cunt. I've been waiting for your cock all this time, that's why I've been a virgin." Anita couldn't believe the words that were coming out of her own mouth, she didn't even know she could think like this.

"That's more like it," he said, as he pushed his thick cock into her.

She screamed as she felt pain surge through her body, but he kept pushing. "Please Master, please keep going," she screamed. She could feel his cock opening her up, and could only imagine how far his cock would go into her.

"Damn, you really are a virgin," he said, impressed with how her pussy wrapped around his cock.

As his cock slid past her clit, she could feel waves of pleasure rolling across her. "YES!" she screamed over and over, as he thrust over and over. Vanessa climbed on top of her and put her pussy to Anita's face. Anita immediately began to eat her out, getting turned on by the fact that she was having a threesome with her best friend and the hottest guy in the school.

"Enjoy the ride," Vanessa said giggling, "He lasts a long time. I told you he knows how to treat women well." Anita felt herself orgasming, but Jason kept pounding her faster and faster. She felt herself orgasm again, as she felt his cock plunge into her for one last time before she felt his warm cum spray inside her.

He pulled out and held his cock to her face as Vanessa moved out of the way. "Don't waste a single dr-", he was cut off as Anita swallowed his entire dick whole and licked every single drop off. "Damn, you're eager," he said chuckling. As she felt the cum roll over her tongue, she felt disgusted with every fibre of her being.

I sat there listening to Anita, who clearly still harboured some feelings for Jason, explain in vivid detail how he had fucked her senseless on her first date. I couldn't help but find myself turned on, as she told me all of this. "Oh... So why did you break up...?" I asked, hoping to hide my emotions. "Well, after that, I felt filled with remorse for what I had done, so I avoided him at all costs. I know he's in our class, but I make sure to avoid running into him." she said. "Plus, I met you and you seem like such a great guy, so I definitely made the right call," she added.

I gave her a smile, trying to hide how ashamed I was at myself for being turned on at the thought of the woman I loved being animalistically fucking someone else. Little did I know that my life would change completely over the next few days.