My Best Friend Regrets It Pt. 02

Although I wasn't completely surprised that Sara and Adrian were not destined to get married, the timing, at least for me, was perfect. I had already been released from Adrian's service, and had received everything that was promised to me. At this point I think I still saw Sara and I getting back together, and I knew it was in my best interests to drive a wedge between Adrian and Sara. For this reason, and because I had a throbbing erection, I persuaded Sara and Svetlana to continue watching the footage.

I fast forwarded until the girls came back into the room. Koko and Jamie came back in holding hands and smiling, as if they had just experienced the most enjoyable encounter of their lives. I knew it was an act. Adrian got his jollies from debasing young women, and having them pretend to be happy about it.

They were wearing matching yellow sundresses, and it evoked a strong reaction from Svetlana.

"Those fucking bitches are wearing our clothes," she said angrily. "They have been rooting through our closets."

Svetlana was very possessive about her haute couture wardrobe. She felt that her beautiful clothes defined her, and Adrian spent thousands of dollars on her outfits. In fact, every weekend Adrian permitted Svetlana to buy a brand new dress or outfit, without much consideration of price. The only caveat was that Svetlana had to model her new clothes the following Wednesday at noon, during her weekly golden shower.

Jamie was about Svetlana's size, and was quite obviously wearing her yellow Dior dress.

"I bet that snooty little cunt wouldn't feel so cute if she knew that Adrian had pissed all over the dress she is wearing," she said, with a sense of satisfaction.

Sara laughed at that, and for a moment seemed less jealous. Her jealousy resurfaced seconds later, as Adrian started to explain a consent form to Jamie.

"This form says you consent to anal sex with me, and you understand that I am going to film it," he began, to a wide-eyed Jamie.

"I am not sure any more Adrian," she said fearfully. "I think you might be too much for me to handle in my virgin ass."

Adrian pressed the issue, taking control of the frightened young girl.

"The whole reason you are here tonight, Jamie," he began in a firm, but measured tone, "is to let me take your anal cherry. I have paid you two thousand dollars for the privilege, and you need to keep your end of the deal. Sign the form."

Jamie was still clearly conflicted, but she signed the consent form with a shaky hand.

"Good girl," Adrian said condescendingly, as he inspected her signature and compared it to her driver license on his phone.

"I know you are out of your comfort zone Jamie, but Koko will talk you through it. I took her anal cherry too, and have butt-fucked her tight little ass many times. Does she look any worse for wear to you?"

"No," Jamie answered quietly, as Adrian asserted himself over her.

"Good girl," Adrian said with a little more compassion. "Koko will get you ready."

Adrian had set up two cameras, each on a tripod, to record the young girl's violation. One was positioned right behind her, slightly off to one side, to capture the penetration. The second was positioned to capture the look on the young girl's face, as she got sodomized.

Adrian had obviously edited the tape, or more likely, had someone with more technological savvy than him, edit it. Either way, the footage was now split-screen and would show the anal assault from both ends.

Adrian left the room to allow Koko to prepare Jamie. He was only gone about ten minutes, but Jamie fought Koko every step of the way, as the beautiful Asian girl tried to ready her blonde friend, for her first ass-fucking.

"I think he is too big for me," she said fearfully. "I don't want to be permanently injured."

"Let me prepare you properly, and it won't hurt too bad, I promise you," Koko assured her. "I was scared to death the first time Adrian fucked my ass, and I wasn't getting paid two thousand dollars. Do you just want to give the money back and leave?"

Jamie looked wistfully at her roommate. "Don't be an asshole Koko, you know the money is already spent," Jamie said, realizing her options were limited.

"Well, it is decided then," Koko responded. "Let's prepare you for him. Are you wearing the butt-plug he gave you?"

"Yes, I have had it in all day like you told me to," the Pastor's daughter replied. "It doesn't feel tight anymore."

"That is a good sign Jamie," Koko said. "It means your sphincter is loosened up a little already. Get up on the coffee table on all fours and I will lube you up."

Jamie climbed onto the low wood coffee table and assumed the doggy-style position. Koko got behind her and lowered Jamie's panties to her knees. A black butt-plug was visible protruding from the young blonde's asshole. Koko removed it slowly, and you could see it had done a great job of opening up Jaime's virgin ass. Koko tenderly applied KY anal jelly to Jaime's butthole and a few moments later she was ready.

Koko pulled the young blonde's panties back up to restore some of her innocence, and she waited patiently for her first ass-fucking.

"What a bitch," Svetlana said with disdain, as the three of us watched the tape. "Waiting there on all fours like a fucking dog, for Adrian to take her anal cherry. Kind of reminds me of Chrissy in Vegas," she continued with a laugh.

I turned towards Svetlana, and she smiled apologetically to me.

"Oops, sorry Chris," she said sweetly. "I will work on my lack of sensitivity. I promise!"

Adrian appeared by the coffee table wearing a nice power suit, and full of confidence, as Jaime waited for him, silently in the doggy-style position. He walked over behind Jaime and stood behind her. The young girl looked nervously over her shoulder, and the camera caught her look of distress perfectly. I swallowed nervously and my cock danced around in my jeans.

It was just the perfect picture of submission. The eighteen year old Pastor's daughter, posed seductively in a Dior dress, in the doggy-style position with her anus lubed and stretched by the butt-plug. Koko had pulled her panties back up, not to restore her innocence, but rather to enable the well dressed black man to unwrap his gift of another anal cherry. The three of us looked at each other, as we realized that Adrian had taken this gift from us all, although my violation was by far the worst.

Adrian picked up the black butt-plug from the coffee table and walked slowly around to Jamie's head. She looked up at him nervously and he spoke.

"Did you use an anal cleanser earlier today?" he asked the young girl.

"Yes, Adrian, I did it twice, as you directed," she replied, her voice trembling.

"Then I take it you are confident that your anal passage is clean?" he said.

"Very confident," she replied, her wavering voice not conveying her confidence by any stretch of the imagination.

"Good girl," he said condescendingly. "Open your mouth and hold this."

He inserted the butt-plug between her young lips, and she obediently held it between them, barely able to hide her look of disgust. Adrian walked slowly back around behind her.

"Unwrap my gift, Koko," he ordered, as Koko slowly removed Jaime's panties.

Once Jaime's panties were on the floor, Adrian slowly unzipped his pants and told Koko to get his cock out. Koko fished his huge black cock out through his zipper and sank to her knees. She sucked his cock for a few moments until it was fully erect, then applied a liberal coating of KY anal jelly. Then she lined the tip of it up with the entrance to Jaime's asshole. Adrian moved forward barely an inch, so that the head of his cock was pushing against her sphincter, and paused for dramatic effect.

Jamie's eyes were wide open, fear visible on her young face. The Pastor's daughter was still a virgin, and she was about to lose her anal cherry before her vaginal one. Adrian had a look of satisfaction on his face, smug in the knowledge that he was the first guy to bust open Jamie's ass. He pushed the tip of his cock through her tight sphincter, and it closed around his shaft as he entered her.

Jaime was very scared and in obvious distress as Adrian eased his massive cock inside her teenage ass. Koko moved round to Jaime's side and was whispering words of encouragement to her college roommate, as Adrian continued to force his way inside.

Jaime was tearing up a little, but didn't speak, presumably afraid of the consequences of dropping the butt-plug, that she now held in her teeth.

"Don't cry baby," Koko whispered gently, "try and relax, it will hurt less."

Adrian didn't give a fuck about Jamie's level of distress or discomfort. He just wanted to get his rocks off. He had paid Jaime two thousand dollars for her anal cherry and, unbeknownst to Jaime, had also paid her best friend and roommate, Koko, five hundred dollars to entice Jamie to step out of her comfort zone, and let him sodomize her.

Once he was balls-deep, he let Jaime gather her wits, and then started to very slowly fuck her ass. She stopped crying and tried to put a brave face on it. As her sphincter relaxed, and her anal passage adjusted to accommodate the length and girth of Adrian's cock, the pain dissipated. I can tell you from experience that being butt-fucked by Adrian is not pleasurable, but it is not entirely painful either.

Once Adrian was in a rhythm, and Jaime was taking his assault without too much issue, Koko moved around to Adrian's side.

"How does she feel baby?" Koko asked. "Nice and tight? You own that ass, is it worth two grand?"

"Fuck yeah, Koko," Adrian responded, "the Pastor's daughter has a tight little ass. She is definitely giving up her anal cherry right now. That is worth every penny I paid for it."

A look of abject shame flashed across Jamie's face, as she processed the fact that this dominant black man, who was old enough to be her father, had purchased her anal cherry.

I looked across at Sara, as the three of us watched the tape and she looked very down trodden. I couldn't blame her. It was only a few days until the wedding and she was watching her fiancé enjoy two co-eds, one of whom was a virgin.

"Do you want me to stop the tape?" I asked.

Sara didn't respond, but Svetlana replied with a resounding, "Fuck no. I want to see what happens to my dress!"

My eyes widened at the insensitivity of Svetlana's comment, but Sara tried to assuage my concerns.

"She has a right to know what happened to her Dior dress," Sara said. "That is a three thousand dollar dress."

The two girls were in agreement about continuing to watch the tape, and I sat silently enjoying the performance.

Adrian had established a steady rhythm as he butt-fucked the Pastor's daughter. Jaime had got over the initial shock of having a huge black cock in her anal passage, and while I wouldn't characterize her demeanor as cheerful, she had stopped crying. She still held the butt-plug in between her teeth, so was unable to speak, for fear of dropping it.

Koko kissed the side of Adrian's face, and scratched his stomach with her manicured fingernails as he sodomized her college roommate. She moved her lips to his ear and started to talk dirty to him.

"Do you want me to suck your nuts while you fuck Jaime?" she asked eagerly.

"Get on the table, Koko, and eat Jamie's pussy," he directed her.

The beautiful young Asian was apparently used to Adrian's direction, because she got onto the low-slung oversized coffee table, and slid underneath Jamie and Adrian, face first. As Adrian fucked Jaime's ass from behind, Koko raised her hand slightly and started to lick her roommate's clitoris. I saw Jamie stiffen up as Koko's tongue teased her genitalia, and one side of the split-screen recording showed her eyes widen.

Koko sucked on Jamie's clit making lewd slurping sounds and the Pastor's daughter was responding favorably. After a few moments the sucking sounds were replaced by a slightly different noise, and it was apparent that Koko's tongue had entered Jamie's vagina. Jamie closed her eyes and lowered her head slightly, as she enjoyed the young Asian's lips on her.

Even though Jamie and Koko were in the sixty-nine position, Jamie did not reciprocate, afraid as she was to drop the butt-plug from her mouth. Jaime came fairly quickly on Koko's face, and I realized that the two college roommates had enjoyed each other in the past. Koko brought Jaime to another very quick orgasm, although she was not very vocal when she came, due to the butt-plug in her mouth.

Adrian realized that the sex toy was inhibiting her enjoyment, and spoke.

"You may drop the butt-plug Jaime," he ordered, "and eat Koko's pussy."

Jamie spat the black silicone plug out, and made a disgusted face, as she processed what Adrian had just made her do. Then, as Koko brought her back to the edge, she slowly lowered her eager lips onto Koko's freshly shaved pussy. Jaime had one more orgasm on Koko's face, and was much more vocal this time.

I saw Koko scoot forward a couple of inches and then Adrian tensed up, as she was presumably nibbling his nuts. Adrian's pleasure was visible from both camera angles. As he faced one tripod, a look of abject pleasure came over his face, as Koko worked to increase his enjoyment. The camera behind him caught him tensing his buttocks under the new stimulation. Jamie continued to eat Koko's pussy as she got her ass fucked.

The back of Koko's head finally emerged from beneath Adrian's muscular ass, and she started to give him a rimjob. He moved his knees further apart to facilitate her access, and picked up the pace of his thrusting into Jamie. A few moments later, Adrian cried out as he ejaculated into the teenager's anal passage. Koko continued to rim Adrian as he composed himself, and he finally withdrew from Jamie's ass. The two girls remained in the sixty-nine position awaiting further instructions.

Adrian stood up straight, and surveyed the two teenage roommates, as they waited passively for his next move. Apparently he decided he wanted Jamie to clean him up, because he walked over to her end of the table, and positioned his still erect cock at the entrance to her mouth. Jamie had a look of disgust on her face as she processed Adrian's latest expectations.

"Suck him clean, Jamie," Koko ordered. "If you cleansed correctly there will be no aftertaste."

The Pastor's daughter tentatively extended her tongue and started to lick Adrian's cock clean. Adrian allowed her to stall for a brief moment, before forcing his cock between her lips. Jaime did suck him clean but she was obviously disgusted by the whole ass to mouth scenario.

After Adrian was satisfied that he had humiliated the young girl sufficiently, he withdrew from her lips.

"I am going to take a shower," he informed them. "Let yourselves out, you may keep the dresses."

With that, he was gone.

Sara looked crestfallen as she absorbed what she had just witnessed. The tape continued to play, and showed two very different reactions to the event, from Jamie and Koko.

Jamie was obviously still disgusted with herself. She was looking down dejectedly, fixating on the black silicone plug that had been in her ass for several hours, before ending up in her mouth. She kept dry-heaving and I thought she was going to vomit.

Koko, by contrast, had got to her feet and was admiring her new Dior dress in the mirror just in front of coffee table. She twirled seductively, as if she was imagining where she might wear it. For her, everything had a price, and she was ecstatic with the events of the evening. She had been paid five hundred dollars to serve Jamie's anal cherry on a platter to Adrian. To top it off, she had been gifted a three thousand dollar Dior dress.

Jaime took her yellow dress off and left it on the coffee table. She apparently had no interest in ever seeing the outfit that she wore to lose her anal cherry, again.

"Well at least I still have my Dior dress," Svetlana said, with her continued insensitivity.

I flashed Svetlana a disapproving look and she realized that she was being inappropriate. She lowered her head to signal her apology, and then said something in a deadly serious tone, that had a sobering effect on the room.

"Adrian will pay for that infidelity, Sara, I promise you," she said ominously. "Ivan feels indebted to us for extricating him from that failing fund, without any financial loss. The Bratva inserted Ivan into Adrian's house to keep close tabs on their investment. They would have cut Ivan's balls off and made him eat them, had he lost their money. I am going to leverage that appreciation into a world of hurt for Adrian. One day I will take Adrian's anal cherry from him, bent over that fucking coffee table."

Sara gave Svetlana a half-hearted smile, but I knew she was deadly serious. At that moment, I felt nothing but love for that young Czech girl, but I was also eternally grateful to be on the same side as her.