Cherise finishes her shower, wraps a towel around herself and blow-dries her hair. She begins to gently brush her hair. "What's the plan Babe?"
"The plan is to get dressed and catch up with the group who are probably watching the sunset and drinking" I respond.
Cherise puts on her bikini, a white beach coverup, and her shorts. Although her boobs are small, they fill out the bikini nicely. She could have been a swimsuit model in Sports Illustrated.
She applies candy crimson shade lipstick, cherry flavored, and asked me if I want a taste.
"You just put it on, Cherise" I bark. "Let's go."
She doesn't seem to care and kisses me with those red candy lips, laughing as she pulls away. Then she turns back to the mirror and applies more lipstick, perfect and deliberate. A quick spray of her "Paris" perfume fills the air, intoxicating me and setting my senses on fire. I want to throw her back on the bed, to lose myself in her, but I hold back. It's time to get moving.
As expected, everyone gathers at the outdoor bar, drinking, talking, cursing, and watching the sun fade over the horizon. One of the owners of the bank, Ray, comes up to us and introduces himself to Cherise. Ray is married but he is a player. But he is also respectful and understands that it is the people like me that makes the bank a lot of money.
Ray is Italian and forty something years old. He has black straight hair and an East Coast accent. He is average height and in good shape.
"You're gorgeous. Isn't Jerry lucky." Ray says.
Having Ray think my girlfriend is hot works in my favor at the bank and for my career. It sounds weird, I know. Ray isn't a typical banker--he's from the clothing business. His friend Arnall talked him into buying into the bank, and now here we are.
Cherise smiles and in a flirty voice responds, "Well thank you Ray. Are you married?" You have to hand it to Cherise, if nothing else, she is direct.
I said in a library voice, "Jesus Cherise". She laughed.
Ray smiles and says, "Yes, but I am not buried." As he gave her hand a gentle squeeze.
I take Cherise's hand and lead her to the side of the boat and away from everyone else and say, "Cherise, I must work with these people. Contain yourself. At least wait until the late evening when everyone is drunk and will forget your antics".
I knew when I brought Cherise that anything that can happen and will happen. She is free-spirited and pushes boundaries. It makes little difference to her whether these are my coworkers and bosses, or my friends from college.
We return to the room to throw on some clothes; nothing fancy, just jeans and shirts. Cherise applies more lipstick and sprays more perfume on herself. "What are you going to do? Turn tricks?"
She responds, "Maybe" and I give her the "What the fuck Cherise!" look.
We rejoin the group, and I end up introducing her to some of the other reps, most of them are men. She is flirtatious and charming. She asks me what I think about the waitress in the bikini with the big tits or my nicely figured coworker who used to work at the Playboy. "Do you want to fuck them?"
I say that I will fuck the waitress if she watches but I am not interested in having sex with my coworker. Cherise likes my answers.
We all proceed to the dining room. There is a long table with a lot of chairs and a bottle of wine for each four-plate setting. The table is set with fancy tablecloths and china. Cherise sits down next to Ray and before I can sit down next to her, another guy sits down-it's my fucking nemeses Rod. Rod's wife is sitting somewhere else. So, I sit across from Cherise, and she gives me the "Oh well" look. Fucking Cherise.
She makes small talk and smiles a lot. She has removed one of her shoes and starts giving me a foot job from across the table. I am too focused on what she is saying and doing to get aroused. But I must admit, it felt great.
Dinner lasts about an hour and a half and some of us, including Ray and Rod, decide to change clothes and go to the ship's dance club, "Amor".
There is Ray, Rod and a few other reps drinking. "Rod, where's Becky?" I asked? I was hoping she was at the club as well. I sipped my Jack and Coke.
He responds, "She was tired, so she went to the cabin. Tonight, I am single, and the ladies will love it".
"What I jerk," I thought to myself.
Ray asks me if he could dance with Cherise, and I say fine. As he leads her out to the dance floor the DJ starts playing "Wonderful tonight". Great-he will have his hands all over her. Instead, he is a gentleman and halfway through the song he suggests that she dances with me.
I whisper to her, "What did you talk about?"
"He wants to know if you would mind if I slept with him."
Ok, not a gentleman but he is direct.
"And what did you say?" I ask.
"I said that I did not mind but you might."
"Ok. Then you need to get a girl for me-you can do that right?" I laugh.
Getting another girl involved, sexually excites Cherise and she quickly excuses herself. She walks over to the bar where a forty something year old woman was drinking a scotch and sits right down next to her. The woman is a little bit chubby and has big boobs with nice cleavage. She is wearing a black cocktail dress that goes down to her knees and low heal shoes. She carried a small black purse with sparkles-it looks expensive.
Cherise makes some small talk and then asks, "Are you here with someone?"
The question surprises the woman. She is not used to Cherise's forwardness. The woman looks a little uncomfortable but plays along.
"Honestly? My Mom but she is asleep already and I am bored"
Cherise picks up the woman's drink and told her to follow her back to where we are hanging out.
"This is Jerry, my boyfriend, Ray who is rich, and Rod who is odd". Everyone laughs, even Rod. I think that Rod knows he is odd and likes it that way.
The woman introduces herself as Christine, and she is from San Francisco and is newly divorced. "It was a loveless marriage, and I finally left him," she says sadly. "It was like we were roommates."
She sees an open door. "Well then we need to make it a lovely night for you."
She is giving me the eye. I assume that she wants me to start flirting with Christine. Ray is already hitting on Cherise while Rod went off with a young girl to dance-too young if you ask me.
I ask Christine how she likes San Francisco and where she lives. I used to live there, so I know the city pretty well. She starts to open up a little, admitting she's been feeling lonely. Then, out of nowhere, she asks me about Cherise and me, and the status of our relationship. This is the first time that she gives any indication that she is open to any kind of sexual encounter.
I tell her that Cherise and I have been together over a year, and we have a playful relationship which is flexible. She smiles. I mention that both Cherise and I find her very attractive. I am sure that makes her good about herself as we are ten years younger than her.
I decide to further test the waters-I ask her to dance. She looks over at Cherise who says "sure," and I take her by the hand and lead her to the dance floor. The DJ is playing "How deep is your love," a slow, romantic tune by the Bee Gee's. I pull her close to be and feel her breasts against my chest. Our hearts beat a little faster and I look into her eyes.
Our dancing catches Cherise's attention. Cherise is turned on, but also a little jealous. I think that is a natural response. I was too involved with Christine to notice Cherise. Common sense would dictate that Cherise will do something to up the ante. She always does.
Cherise redirects her attention on Ray. She asks Ray if he would like to go back to his room and have a drink. Ray says of course he would, pays our tab, and walks away with his arm around Cherise.
"Where is she going?" Christine asks.
"Probably to Ray's room." I answer. Christine looks surprised.
I decided to be direct.
"Cherise doesn't care what we do together. Let's go back to my room and have a drink. It is more private."
Christine thinks about the situation. It has been two years since she has had sex. She was already turned on and the thought of being intimate with a man was very tempting. She decides to slow the pace a little. "Dance with me. I need some encouragement. This is new for me."
She takes my hand in hers, and we return to the dance floor. By this time there are only a dozen or so people left in the club, none of whom are from my company. The DJ is playing "When a man loves a woman." Oh boy, Cherise loves this song.
