“Have you ever had anal sex?” he asks.
He hit my main concern right on the head – or my old main concern, now that I’m totally down to be doubly penetrated. It’s true I’ve never let a guy put his dick in my butt, but that mainly due to the fact that I just didn’t feel comfortable enough to do that with any of them.
“No, but I never did a lot of things I’ve done with you guys and I know it’s kind of sudden, but I like to have all of these new experiences and this is actually something I’ve been thinking on for a while now. Ever since we had sex at the office, it’s been a thought in the back of my mind and, at first, I thought the fact that I’ve never done anal might be a problem, but now I don’t feel like it matters. I want to feel both of you inside of me at the same time. If you’re okay with that.”
Zane nods after listening to my little speech. He seems open to the idea and I’m already excited. Simply thinking about the two of them inside of me has me immediately wet. I’m so wound up, I’m pretty sure if I applied the slightest pressure to my clit, I’d be orgasming violently.
Zane finally responds, and he answers the way I has hoped he would. “Yeah. If you’re completely comfortable, I am completely comfortable.”
I throw my arms around his shoulders and kiss him. It quickly turns from an innocent kiss of excitement to a lustful kiss, anticipating the upcoming sex. We’re both on our knees and my body is flush against his. His erection pushes into my belly, its hardness making my pussy clench. The bed dips behind me and I feel Whit kiss the tip of my shoulder before taking my hair out of the messy bun I put it in. He wraps my hair around his fist and pulls it back with a quick, forceful motion. I cry out in pain and look into his eyes.
“We’re going to need to get you undressed,” Whit orders.
I nod, biting my lip. He takes his hand from my hair and lightly kisses the side of my face. I untangle my limbs from Zane’s and get off the bed, so I can strip with their eyes on me. I’m only wearing my thin pajama set, so I slowly peel everything off me body. I start with my shirt. I push the strap off my right shoulder and then do the same with my left. I’m not wearing a bra, so when I pull the tank top down, my breasts are immediately exposed to the cold air. My nipples are hard and peaked and I graze my hand over them, causing myself to gasp. As I push the camisole down my body – when I get to the top of my shorts – I push them down too. I leave my underwear, so when I stand up and step of my clothes, I am left in my black satin panties.
Zane and Whit get off the bed and I stop moving to see what they are about to do. They start to undress, following my lead by going slowly. I watch their muscles being revealed. I’ve seen their bodies a few times at this point, but I can’t help but drink it in every time. They keep themselves in good shape, but they also aren’t overwhelmingly buff. I love running my hand down their bodies, feeling the dips of their ab muscles on their torsos. Being able to feel them move under my hands just feels… so good.
We’re all down to just our underwear and then – together – we pull them down. I’m not entirely sure what I’m supposed to do. I’ve never done something like this and I don’t know how to place myself on the bed. Whit and Zane sense my hesitation, they come over to me and take my hands. We walk back to the bed together.
“We’re going to do this lying down,” Whit tells me. “It’ll just be easier for you the first time.”
I nod, and I get on to the bed in the middle. Zane and Whit are on either side of me. Zane takes my shoulder and tilts me towards him. I lie on my side and Whit comes up to my back, almost flush against me. I take a deep breath, starting to feel all kinds of feelings. It’s just something outside of the realm of what I’m used to. I mean, that’s what this entire experience has been – outside the realm of anything I have ever done. I take a deep breath and I run my fingers down the side of Zane’s body. He lifts my chin with his hand and gives me a soft kiss.
“I need you to relax,” he says against my mouth. “If you’re not relaxed, this isn’t going to work.” He pulls back a little and looks into my eyes. I nod because that makes sense. That’s what my friends would always tell me. So, I close my eyes and take a few breaths. Some of the tension that has gathered in my limbs dissipates.
Whit's hands are all over my ass. He rubs up and down my ass cheek and asks, "Before we can start, we'll need some lube, especially if it's you're first time.”
I look at him over my shoulder and point to the nightstand. "There should be some in there.”
Whit cocks his eyebrow in surprise. I'm assuming he didn't expect me to have any lube, but I bought it because I thought I might have anal sex and I wanted to be prepared. Look who was right. I hear the drawer open, some rustling, and then the drawer close. More sounds come from Whit's side: the bottle opening, the lube squirting out, etc. It's all making me anxious, but I keep my body relaxed per Zane's instructions. He's stroking my face, looking at me with a look I haven't seen on his face before. I want to ask him if something is going on, but I feel Whit's hands spread my cheeks and he circles my asshole with a lubed-up finger. I brace myself on Zane's shoulders, gripping them with my hands. Whit starts with one finger, stretching me out. My breathing picks up and my toes curl at the foreign feeling.
"Are you doing okay?” Zane asks.
I nod. He begins kissing me, taking my leg, and having me lazily wrap it over his. Gently, he holds my face, continuing to explore my mouth with his tongue.
"Can I add another finger?”
I nod, and Whit puts in one more. He slowly adds all of his finger fingers, stretching me more than I have ever been back there. My heavy breaths turn into lustful moans. I'm so sure I'll come just from this, but Whit removes his hand from my bottom.
He brings his mouth to my ear and whispers, "Are you ready?”
"Yeah,” I whisper back.
Zane starts us off by lifting up my leg, hooking it in the crook of his elbow. He guides the head of his penis into my pussy entrance. My walls stretch to accommodate him. Just when he's situated, Whit positions the tip of his shaft at my… other entrance. He moves even slower than Zane, starting and stopping as my body tenses. He whispers to me, doing his best to keep me calm. It feels like I'm being pried apart, but it's not just pure pain. There's pleasure there, too. It starts out small, warmth growing from my center, but it's slow to grow. Once Whit is all the way in, the three of us stay still. I wrap my hand around the back of Whit's head, reaching behind me. He kisses the back of my head.
“Ready?” he asks again.
I nod. He slowly pulls out of my ass and then just as slowly pushes back in. The piercing on his dick head rubs inside my ass. Zane starts moving too. His dick slowly slides in and out of my pussy. Their rhythm starts out choppy and slow, but then they start moving together - driving in and out of both my holes.
“Oh shit,” I whisper to no one in particular.
Being this filled with cock is like nothing I had ever imagined. Everything in my being is on fire. My body is tight, but with each fucking pump it is wound more and more. My limbs get loose, and I am lost to the sensations. My head lolls back and rolls from shoulder to shoulder. Zane speeds up, thrusting into my pussy faster. My pussy tightens gripping him harder. My ass hole clenches Whit’s huge cock, and he starts to pump me harder as well. The feelings of pleasure are so intense, I feel almost delirious. Whatever I am saying, I can't make sense of it. It's probably along the lines of fuck me harder and Jesus Christ. I've never felt anything like this.
Whit is quite large, but my body conforms to him. His piercing rubs against my insides adding to sublime friction. My fingernails dig deeper into Zane's flesh. My head is thrown back as I feel Whit and Zane erections grow before they both grunt and come inside me, spilling their seed. My body trembles before my walls quiver around Zane and I clench down on Whit. I shake for what feels like forever, my orgasm rushing into me in a seemingly never-ending wave. I close my eyes, so I can experience every nerve ending on fire, overwhelmed by feeling
s new and old.
Once I'm finally able to calm down, I take a deep bread and look at my boys. Like me, they are covered in sweat and look satiated. They remove themselves from my body. I grunt at the sudden feeling of emptiness, but they snuggle against me, filling that void.
"You were amazing,” Zane whispers. His breath tickles my skin and I smile at his praise.
“You weren’t too bad yourself.” I tap his nose with my finger and then turn to Whit. “Thanks for being so patient. Both of you.”
While I didn’t have my first first time with them, I’m glad we were able to pop a cherry of mine together. I don’t think there’s anyone better I could have done something like this for the first time with. “I need to go to the bathroom. I’ll be right back.”
I get off the bed and head to the bathroom. I pee and while I’m washing my hands, I take a long look at myself in the mirror. I know I don’t look different, but I feel different. And it’s not just because I had anal for the first time. This entire weekend has been on long daydream. I’m worried if I blink, it might all go away. That might sound a little ridiculous, but I’ve never felt this good in a romantic relationship and I’m worried it could all get destroyed.
I go back to my bedroom and get in between my boys. We all snuggle together and fall asleep in one another arms.
Chapter Seventeen:
Chloe
I wake up the next morning to knocking on the door. I’m surprised that Whit and Zane aren’t awakened by the noise. They are usually such light sleepers. I rub my eyes and get out of the bed. I realize I’m still naked, so I go and put on the pajamas I threw on the floor last night.
Once I’m dressed, I go to the front door of the guesthouse and look through the peephole. Oh, shit! It’s my Dad! I freak out like I’m still naked and then remember I’m already dressed. But then… oh, shit! I have two naked men who also happen to be the CEOs and lead lawyers of my Dad’s firm and if he walks in on the three of us he would no doubt have a heart attack.
“Chloe! Chloe! It’s your father. I know you’re in there.”
I can’t pretend to not be here because my car is out in the driveway, but what is he doing here? He’s supposed to be in the ocean on his yacht. Shit, shit, shit… I take a deep breath, looking back to the room one last time. Hopefully, Whit and Zane will stay asleep while I’m talking to my Dad.
I slowly open the door, acting like I just woke up. I rub my eyes and fake a yawn, feigning surprise at seeing my Dad. “Dad! What are you doing here? I thought you were on your yacht…”
He smiles. I step out, closing the door, so he doesn’t feel inclined to come inside.
“I realized I wasn’t ready to be away from everything and decided to come home early.”
“Dad, it’s only been like four days. Maybe five. That’s barely enough time to decide.”
One of the few reasons I agreed to work at the firm was because he was considering retirement. He needs to stop working himself so hard and retirement would give him just that. I don’t have time to argue with him here, so I do what I can to get him away from the guesthouse.
“I know, honey, but I feel like that’s enough time for me. I know I said I would really do this, but it just doesn’t feel right for me, you know.”
I’m so annoyed, but he’s also my Dad and I know where he’s coming from and who he is.
“Look, Dad. I’ll come to the kitchen and make us breakfast. We can talk about everything that’s been going on at the firm and you can tell me all about your short trip. I’ll make the waffles you like.”
That last part of my suggestion seems to convince my Dad and he says that he’ll see me back at the house and I go inside the guest house, thanking god for my insane good luck this morning… or whatever because it’s not good luck that my Dad came back early.
I go back to my room and Zane and Whit are awake and dressed. I look at them and I’m about to explain what just happened, but it seems they already know.
“We heard you talking to your Dad. Is everything okay?” Zane asks.
I bite my bottom lip and nod. “Everything is fine, but, obviously, you guys have to go.” I twist my mouth to the side and tap my foot. There’s nothing for me to be nervous about – not really. But I’m already fast-forwarding to the future where I have to either break things off with Whit and Zane or tell my Dad everything that’s happened. Either way, there’s going to be some kind of confrontation.
“We understand. We’ll see you at the office.” Whit looks at me expectantly – like he knows I’m holding back. He probably knows I’m holding back is because he’s so fucking good at reading people. I do my best to hide the negative feelings swirling up in me by pushing them down and ignoring them for the time being.
“Yeah. Wait a few minutes. I’ll be with my Dad in the kitchen, so you guys shouldn’t run into him.”
They nod, and I leave the guesthouse to go to the kitchen. My Dad is waiting for me, sitting on one of the stools at the counter. He’s on his phone, either answering an email or playing a game. That’s honestly all he ever does on there.
“Hey, tangerine. I’m excited for your signature waffles.”
I always internally cringe a little whenever my Dad calls me by my childhood nickname. It originated because I was never able to peel a tangerine by myself and I would always ask my Dad – never my Mom – to peel them for me. It stuck because I took me a long time to peel it on my own. Way into high school. But after I internally cringe, I’m filled with a warm fuzzy feeling because of the memories.
“Do you want to help me make the batter?” I ask.
He gets off the stool and we begin to mix all the ingredients. My Dad takes the dry and I take the wet and then I put them all together. He goes back to the stool while I use the waffle iron. We make small talk while I cook, staying away from what we’re really here to talk about.
Once I’m done, we sit down across from one another and dig into the waffles. There’s nothing really special about it. It’s chocolate chip waffles with some vanilla extract. After a few bites, I bring up my Dad’s trip.
“So, why did you come home so early Dad?”
He takes a few more bites of his waffles and then answers, “Like I said. I wasn’t really enjoying being on the yacht and I felt like I should come back.”
I know my Dad is saying he wasn’t having fun on his pseudo-retirement, but I know he also isn’t having fun at the firm. He’s doing it because it was what he was always done. He does love the firm, but it isn’t the place for him.
“Okay, Dad.” I’m not going to have this discussion with him again. We’ve had this talk before – that’s what we did when we decided I was going to intern for the summer. There are only so many times I can tell my Dad I know he isn’t happy. He has to figure it out for himself. “What are you going to do when you are back?”
“I’m thinking about going back to work tomorrow. We can go in together.”
“Yeah.”
I know Whit and Zane will be a little discouraged by my Dad coming back. They’re probably going to think he doesn’t trust them. I know that’s not it, but who knows if anyone is going to believe me with whatever I tell them.
My Dad and I finish up our meal and we spend the rest of the day together. I don’t need to call in sick today because Zane and Whit know I’m with my Dad, so I don’t have to explain anything to them just yet.
***
The next day, my Dad and I go into the office together. Everyone in the office is happy to see him. Everyone here loves him and of course they are happy to see him back early. We go up to the top floor, Whit and Zane are waiting. My Dad shakes their hands in welcome.
“Thank you, both, for watching after the firm so well,” he tells them. “I know we’d planned on me being away for three-months, but while I was on my yacht, it didn’t feel right. Being so far away from anything – it just felt off. Coming back was the thing for me to do.”
I’m surprised neither of them seem too
concerned about it. I mean, Whit is always hiding behind his cool demeanor, but even Zane is preoccupied.
“Of course, Jack,” Zane says. “You need to do what you feel is right.”
“We are always happy to have you hear, Jack,” Whit chimes in.
My Dad offers his hand to them again, smiling. They all shake again. Dad awkwardly pats Zane on the shoulder.
“Excellent boys. Keep up the good work!” He turns to me and kisses me on the forehead. “I’m going to my office Tangerine. I will see you at lunch.”
I’m about to go sit at my desk, but Zane motions for me to come to them.
“Can you come into Whit’s office? We wanted to talk to you about some stuff,” he asks.
This is probably exactly what I think it is. It’s going to be all kinds of questions about next steps and I haven’t even decided what I’m going to do after work today. Right now, it’s just day-to-day for me.
We get into Whit’s office and Zane and Whit are leaning against his desk. I stay by the door, closing it behind me. There’s no way I want my Dad to hear anything that’s about to go down.
“You guys wanted to talk to me?”
Whit narrows his eyes at me and he’s definitely wary of me right now. My hesitancy isn’t being very well hidden.
“Yeah. We wanted to talk about our relationship. Now that Jack’s back, everything has obviously changed.” I can tell Zane’s really thought about this. Whit probably has, too, but he hasn’t said anything, yet.
“Yeah. Things have changed,” I admit. I don’t know where he’s going with this, but I’m really trying to appear calm.
“We wanted to let you know, we don’t like the idea of sneaking around behind Jack’s back,” Zane continues. “It makes our relationship feel dirty if we act like it’s some kind of secret. We don’t want you to be a secret. We don’t want us to be a secret.”
“We want to tell Jack that we’re all together. We want to make our relationship official.” Whit reaches out and grabs my shoulder. I gently move back, out of his reach, crossing my arms in front of myself. I take a deep breath and get ready to dash their dreams and break my own heart.
Two Bad Bosses_An MFM Menage Romance Page 12
