Betting on Bailey

Two kisses, and a whispered invitation, and I’m going over to Daniel’s place to have sex. Shouldn’t I be more interested in finding a more conventional relationship with guys that are more in my league?

“What should I do?” I ask Gabriella, who has become my unofficial threesome coach. “What should I wear?” It’s Friday night, and she’s at Piper’s apartment, watching me fret with an amused expression on her face.

“You like adventures, don’t you Bailey?” she asks. “Go have one.” Then she grins wickedly. “And it doesn’t really matter what you wear - it doesn’t sound like it’s going to stay on for long.”

I throw a pillow at her. “You are not helping.” I smooth my palms against my jeans. “I’m really nervous about this.”

“Why?”

“What if I don’t know what to do? What if it just sucks? What if they just laugh at me and tell me they were joking about wanting to sleep with me?”

She rolls her eyes at me. No doubt she thinks I’m ridiculous, fluttering around like an anxious sparrow, picking up everything in my room and setting it down, not knowing what to do with the restless energy that’s running through my blood.

“I’m not even going to dignify that last question with a reply,” she retorts. “As for the rest, if it sucks, don’t do it again. And what to do?” She forms a ring with the fingers of her left hand, and mimes her right thumb pumping in and out. “Surely you know what to do?”

“Stop laughing at me,” I say crossly. “I know all about…” I mirror her gesture. “I just don’t know what to do when you add another hand to the mix. Or another dick.”

“Have you ever had anal sex?”

“Whoa,” I feel my face turn fiery. “Way to be direct, Gabby.” She’s identified the heart of the problem. I don’t think I have enough sexual experience for something as adventurous as a threesome. Trevor was a missionary man, with an occasional bit of oral when he was feeling extra-frisky. Ivan would sometimes spank me, but that was in the early stages, and it was never more than a swat or two.

“Well?” she persists. “Have you?”

I shake my head. “Nope. Never.”

“Are you opposed to it on principle?” she asks curiously.

I snort. “Gabby, I’m contemplating a threesome here. No, I’m not opposed to anal sex on principle. I just haven’t…”

She shrugs, unconcerned once more. “In that case, just be honest with them, Bailey, and everything will be fine. Being an anal virgin isn’t a sin, you know.” She laughs. “In fact, I’m sure the opposite is true in some parts of the country. Isn’t having anal sex illegal in parts of the country?”

“Sodomy is still against the law in fourteen states,” I quip, then I become serious. “Should I go, Gabby?”

“I can’t make that decision for you, Bails,” she says. “But ask yourself this. Are you hesitating because you don’t want them or because you are scared?” She curls up on the couch and bends forward to lift Jasper into her lap. “You want to know what I think?”

“Do I?” I ask wryly, more than a little afraid of what she might say. “Okay. Hit me.”

“Remember I love you,” she warns. She gestures at me. “But seriously, look at what you are wearing.”

I look at my outfit. Black t-shirt, dark wash jeans. That’s the uniform on days I don’t have to teach. When I have students to deal with, I upgrade to a black pantsuit. “Let me guess, you don’t like black?”

“I like black just fine,” she responds. “You, on the other hand, dress in boring clothes and date boring men. You’re smart and you’re bright and you are really pretty, but you like to hide all of that, because it’s easier to do that than to risk failure by putting yourself out there.”

I stop and look at her, stung by her words. “That’s not true. It isn’t my fault that Trevor was a jerk.”

“No, but it’s your fault that you moved in with him anyway.” She waves away my protest. “Look, forget Trevor. Tell me, do you think these guys are attracted to you?”