CHAPTER SIX: CASSANDRA DOES A DUO
This is the sixth chapter in an ongoing erotic romance novel about a client and a sex worker. In this chapter, Cassandra gets invited to do a duo massage and gets caught up in the excitement of being with a woman for the first time.
Table of Contents:
1. Oscar Shares A Secret
2. Cassandra Falls for her Client
3. Oscar Takes a Chance
4. Cassandra Heals the World
5. Oscar “Cheats” on Cassandra
6. Cassandra Does A Duo
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CASSANDRA DOES A DUO
Dancing with Derek was extremely fun and extremely erotic. But it was nothing like dancing with Gloria. Dancing with Gloria was the most free that Cassandra had ever felt. There was something about dancing with a purely unselfconscious, powerhouse of a woman like Gloria, that liberated Cassandra in every fiber of her being, from every prison she'd ever lived in.
Past prisons included her childhood home, public school, pregnancy, life as a lawyer, and currently her relationship with Derek. Tonight, Cassandra broke out of every prison, metaphorically-speaking, through the unleashing of her soul. Dancing was everything Cassandra needed and Gloria's Goddess vibe only served to lift Cassandra higher.
She danced off all the stresses and uncertainties of her life. She danced off the clients who were needy and demanding. She danced off her obligations to her daughter and her mother. Derek faded into oblivion, as Cassandra engaged every muscle in her body in a celebration of music and existence.
Gloria flirted with her, making eye contact often. There was a sensual vibe to their congruous movements that made Cassandra's nipples harden and caused a fire to form between her legs. She'd been attracted to women, but she'd never been with a woman before. She'd never really had women friends either. She wondered if Gloria was just being a fun friend or if she was coming onto Cassandra in a way that was too subtle for men to pull off.
After a few drinks and dances, Cassandra felt relaxed for the first time in forever. She returned with Gloria to a booth where Gloria's client, Brad, kept their drinks refilled and watched their purses. He knew that Gloria would reward him grandly at the end of the night when she was done wielding her pussy power on the dance floor.
Brad was charming and conversationally-gifted. He told interesting stories and made Cassandra feel like he was interested in what she had to say. Watching the two of them together, Gloria appeared as though she was absolutely in love with Brad, which seemed odd because he was a client who booked her exclusively, but he was not a real boyfriend.
Brad was Gloria's current long-term client. That was her service. She traveled with and nurtured the wealthy, businessmen who hired her for companionship, events, and intimacy. Some relationships lasted months and some lasted years. Brad was a relatively new client which might explain the giddy way Gloria behaved with him.
When Brad went to the bathroom and they were alone, she boldly asked Gloria, "You seem to be very in love with Brad. Are you an incredible actress or what am I seeing?"
Gloria laughed. "Well, I do love Brad, in a way. If I didn't, I wouldn't be able to commit to our exclusive arrangement. And Brad is a beautiful, charming, intelligent man. Isn't he wonderful?" Cassandra nodded. "If you're asking me if I'm in love, the answer is no. Sometimes I wonder if I am even capable of falling in love. I really do cherish my independence, you know."
"Yes, I know exactly what you mean. There is zero part of me that wants to live with Derek. But I'm loving the hot, intimate, passionate sex. So, I'm keeping him around for now." Although she played it cool with Gloria, the truth was that Cassandra's feelings for Derek scared her. She was more attached to him than she wanted to be.
Gloria interrupted her thoughts. "Before Brad comes back, I wanted to ask you something. Well, actually, it was his idea but I agreed with him. Would you be interested in doing a duo massage with me later tonight? Brad pays really well and don't worry, I told him you only do massage."
Cassandra was feeling pretty aroused from dancing and flirting with Gloria all night anyway. Why not make some money doing something she will likely enjoy? "Sure," she said. "Sounds fun." Her eyes sparkled as she returned Gloria's intense, sexy gaze.
They danced again and Cassandra's arousal grew as she imagined kissing Gloria and pressing her breasts against Gloria's breasts. She wondered if a duo massage might include some lesbian lessons from her friend. The thought made her laugh with joy. She had never been so sexual before becoming a sex worker. It was incredible how free she felt.
Sensing Cassandra's mood, Gloria ushered Brad and Cassandra into Brad's waiting limousine. With a kind smile at Cassandra, Brad said, "I want you to know that you're safe with me and if you change your mind or want to leave at any time, you are absolutely free to do that."
Gloria giggled. "Of course she knows that, Bradley. But thank you for showing her you care." She nuzzled closer to him, running her hand up his inner thigh and resting it on his cock. "Oh Baby, you're already getting hard," she purred. Cassandra felt herself getting the female version of hard at her words.
She looked at Brad for what felt like the first time. She hadn't assessed her attraction to him before this moment, lost only in her attraction towards Gloria. He was a gorgeous man. Gloria was right about that. He had great posture and he exuded confidence. Dressed in a smart button-up shirt that barely hid his bulging biceps, Brad was looking good enough to eat.
She felt a twinge of guilt for looking at another man, especially knowing how jealous Derek was. But it was his jealousy precisely that pushed her away. She couldn't imagine Brad ever being jealous. She decided to ask him. "Brad," she said, "Are you the jealous type? Do you ever get jealous of another man paying attention to Gloria?"
"Why do you think I pay her to be exclusive?" he replied. For a moment, Cassandra thought he was serious. But then, Brad and Gloria both laughed.
"Brad's not jealous at all," Gloria said. "He encourages me to flirt and we've even invited the occasional man to join our festivities, if you know what I mean." Cassandra was surprised. Her imagination began to run wild. Did Brad like to watch Gloria with another man, or did Brad engage with the man too? She didn't ask because it was none of her business. But the thought of Brad making love to another man made Cassandra even hornier.
When they arrived to Brad's oceanside home, music was already playing through invisible speakers and a fire was lit in the fireplace. Wow, he must have servants who prepared everything before our arrival, Cassandra mused. Gloria and Cassandra climbed onto a long, red couch while Brad poured them drinks, then joined them.
Gloria sat in the middle. She was the link that bound them in their little triad. Cassandra commented on how beautiful Brad's home was, but it was only a few minutes before Gloria turned to her and started running her hand up Cassandra's inner thigh and under her skirt. She leaned forward and Cassandra felt her heart skip a beat because Gloria was about to kiss her.
When their lips touched, Cassandra's entire body lit on fire. Almost too gently to feel, Gloria swept a finger down the crease between Cassandra's pussy lips where her moist panties clung to her the most. The tease was a promise that Cassandra began to yearn for. She returned the kiss, deepening it and pushing her pussy towards Gloria. But Gloria continued to hold back, caressing only Cassandra's inner thighs and outer pussy lips.
As they kissed each deeply and made out mindlessly on the couch, Brad positioned himself behind Gloria, kissing her neck as he reached around to cup her breasts with his hands. He ran his fingers around her nipples, tenderly compelling them to harden. Gloria moaned with Cassandra's tongue in her mouth and Brad's cock pressing into her from behind.
"Can I touch you, Cassandra?" Brad asked, still separated from Cassandra by Gloria's beautiful body. They still had their clothes on, yet this was already the most erotic experience Cassandra had ever had. She nodded her consent, with a delirious smile, then she leaned forward and began to kiss Brad over Gloria's shoulder.
Gloria took this opportunity to begin undressing Cassandra, pulling her own clothes off as well. Brad and Cassandra kissed passionately, running their hands over each other's bodies. Brad's cock bulged in his trousers. They split apart when Gloria lifted Cassandra's dress over her head, coming back together immediately.
Cassandra knew this wasn't what Gloria had suggested nor what she'd agreed to. She was supposed to be giving a massage, not making out with her friend's client. She thought she should feel ashamed about it because Derek would be so angry, but she didn't want to think about that right now. She wanted to stay lost in this feeling of freedom she'd been hanging onto all night.
Gloria started to undress Brad, unbuttoning his shirt while she nibbled on his earlobe, then getting his pants undone to release his gorgeous cock. He moaned as Cassandra's hand closed over it. They were both on their knees on the couch facing each other now.
Gloria knelt on the floor in front of them, and pulling Cassandra's legs gently apart, she began to lick and kiss Cassandra's inner thighs, grazing over her pussy with hot breath and long licks everywhere except where Cassandra's fire burned the hottest.
Just when Cassandra thought she was going to go blind with need, Gloria stopped and Brad began to slowly slide his finger into Cassandra's lustful cunt. Gloria turned her attention to Brad's cock, licking and sucking it enthusiastically. "Oh Baby," Brad groaned, as he slowly finger-fucked Cassandra.
To her surprise, Cassandra realized she was whimpering with arousal. Feeling Brad's fingers entering and playing with her pussy was all she could focus on. She was beyond turned on. All she could do was be carried on the waves of her arousal and take instructions because she'd left her mind several minutes before.
Gloria asked her to lay down. With a twinge of regret, Cassandra felt Brad pull away from her, sliding his fingers out of her hot, wet pussy. She laid back on the couch as instructed and watched as Gloria positioned herself between Cassandra's legs.
As Gloria began to run her tongue along the folds of Cassandra's pussy, Brad came up from behind Gloria and began to do the same for her, kneeling down and licking her from behind. "Please tongue-fuck me, Bradley," she said before resuming her oral ministrations on Cassandra. Brad reached his tongue into her pussy as requested.
While Gloria went down on her, Cassandra could feel her pleasure building. Gloria brought her to the edge of orgasm and held her there, suspended like a star above the earth. Then, she was past the point of no return and she came hard, grasping her fingers into Gloria's beautiful red hair, a beautiful starburst of colours flashing in front her eyes. Gloria expertly held her hand over Cassandra's clit while the convulsions continued and turned her attention to Brad's tongue in her pussy.
Now, Brad began to tongue-fuck her ass. Gloria moaned in pleasure, leaning over Cassandra's body, then guiding Cassandra's hand to her own pussy. Cassandra began to finger-fuck Gloria while Brad tongued her ass. With her other hand, she caressed Gloria's nipples, then held them to her mouth so she could flick her tongue on them.
Cassandra had never made a woman come before, but she felt for Gloria's clit and began to rub it very gently with the flat part of two fingers held together. This was how she liked it but she had no idea if other women liked it that way too. Careful not to rub her clit directly or to pull back the hood, she alternately fingered Gloria, using her wetness to make her fingers slippery and gentle over her clit.
Gloria began to moan with pleasure, leaning into Cassandra's hand and kissing Cassandra hungrily. Seeing what was happening, Brad continued to lick Gloria's ass from behind. It took only seconds of this before Gloria buckled into an intense orgasm. She was vocal as she came. If they didn't know better, they might have thought she was crying. She expressed her ecstasy with zero self-consciousness.
As Cassandra and Gloria attempted to pull themselves together, Brad went to the washroom to wash his hands, brush his teeth, and rinse with mouthwash. He returned with more drinks to find Gloria looking into Cassandra's eyes and toying with her disheveled hair. "You two are the hottest women I've ever been with," he said.
Cassandra giggled. "Just how many times have done this?" she asked.
"I've had a few threesomes but nothing ever like this," he said, with wonder and admiration in his eyes and voice.
"Yeah, most duo massages don't look like this," Gloria said, laughing. "But I hope you're having fun, Cassandra."
"Oh yes, I am having the most fun, " Cassandra reassured her. "I wasn't expecting it to turn out like this either but I guess we were all just really horny."
"Were horny? Are we already done?" Brad sounded disappointed. Gloria looked at Cassandra.
"I think I still owe you a massage," she replied, raising her eyebrows suggestively.
"That sounds amazing, shall we move to the bedroom?" Brad suggested. The ladies nodded and grabbed their drinks before following Brad to his bedroom. He laid facedown on the bed, completely naked, while Gloria and Cassandra began to massage his back, ass, and thighs.
But it didn't last long before Brad rolled over. "I can't wait anymore. Can I fuck one of you?" he pleaded earnestly.
Gloria laughed. "Is it already time for you to come? We've just started."
"This is the hottest night of my life. I don't know how much longer I can hold out." His impish but sincere grin won them out.
"As much as I'd love to, I don't feel right fucking you because of Derek," Cassandra said. She was regretful, but she also knew she could not live with herself if she cheated on Derek. Up to this point, everything she'd done was extremely erotic but other than kissing Brad and finger-fucking Gloria, nothing had been completely outside of her work boundaries.
Before now, Derek had been the only client she had ever kissed. Gloria was now the only woman Cassandra had ever kissed. Although she enjoyed kissing Brad. It wasn't the same as kissing Derek. Or Gloria. Oh my, that was something else.
"Understandable," Gloria replied. "But before I fuck my boyfriends brains out, would you like some more of me, Darlin'?"
"If you don't mind, I'd like to watch you two while I touch myself," Cassandra replied.
"You can do whatever you want," Gloria said. She turned to Brad, took his cock into her mouth, and got him lubed up good to take her pussy. As she perched over him and slid her cunt onto his cock, she made eye-contact with Cassandra. Slowly, she fucked Brad, grinding against him as she watched Cassandra pleasure herself.
Her movements became more urgent and she began to kiss Brad as she rocked on top of him. This turned Cassandra on. She could feel herself getting close to orgasm too. Then, as Gloria began to moan in ecstasy, she turned her gaze back to Cassandra locking eyes and sending Cassandra into another blinding orgasm of her own.
Now Brad groaned loudly, gripping Gloria's hips as he thrust himself inside of her again and again until he, too, exploded with primal ecstasy. No condom, Cassandra noticed. She hadn't seen them put one on. This must be part of the exclusivity agreement. She used a condom with Derek because she wasn't on birth control but often, he would fuck her for a few minutes without it because it felt so good for both of them.
The three lovers dressed themselves together, talking and laughing about all they'd done that evening. Cassandra kissed each of them tenderly before saying goodbye. Gloria stopped her at the door. "Don't forget your money!" She handed Cassandra an envelope. "It's $2000," she said. "He had an amazing night and hopes you'll want to do it again."
"Hell yes," Cassandra laughed as she replied. She hugged her friend one more time, locking eyes for a moment of silent acknowledgment at what they'd shared. Their connection had been special tonight. With one last smile, Cassandra walked out the door, got into the limo and tried not to think about Derek while the driver took her home.
I hope you enjoyed this chapter in the Cassandra and Oscar fictional sage that follows two people, a sex worker and a client, through the peaks and valleys of their lives.
Love Annie xoxo