But enough looking back at what could have happened, though. Wishing for a different past isn’t going to change the future, never has. I have to focus on making tonight a magical evening with Callie.
I prepare two courses for our dinner, knowing she’d be bringing the dessert. My “birthday” cake. Just as I’m finished plating our food, I hear the knock I’ve been dying to hear all week. I open the door and find Callie, looking better than before. I was already attracted to her when I met her but she cleans up extremely well. Without her stained smock and dress shirt, she looks far more seductive. She’s wearing a tight black dress, has her hair put up in a bun, and has her face made up like a model from a vintage pin up catalogue. Bright red lipstick, dark eyeshadow, and even a Marilyn Monroe-style beauty mark.
“Happy birthday”, she sings holding out a fairly sized box.
I thank her for the cake and hug her as she steps into my apartment.
“Nice place”, she remarks as she looks around the room. “I’ve always wondered what the inside of the apartments look like in this part of town. Swanky.”
I grab her hand and gently lead her to the roof of my apartment where I’ve organized our dinner date. The two of us sit underneath the night sky while we enjoy some homemade gourmet food.
“You may be a great baker”, I start saying, “but I’m great with meats. And veggies. Basically anything that isn’t a pastry.”
“I’ll be the judge of that”, she snidely jokes as she starts eating the food.
Callie cuts into the steak I prepared and with the same forkful, stabs through a bit of asparagus I served on the side. She takes it all in one mouthful and slowly savors it. Seeing how much she’s enjoying having that food in her mouth, I lean back with both arms resting behind my head.
“Am I right or am I right?”
“Fuck, you’re so right. It’s been so long since I’ve had food this good, my God”, she ecstatically moans before shoving a second forkful of food into her mouth.
The anxiety that was plaguing me before her arrival melted away rapidly as I watched her enjoy my cooking. Once more, she was able to unknowingly bring a slowly growing smile on my face. Throughout the entirety of our meal, I’m treated to her moans of pleasure between some delightful conversation. Callie goes very in-depth into how her bakery is run by just her and her friend, Sheila. As time goes on, I find that her bakery is the only topic Callie is able to go on about. I try to bring up some movies she’s seen recently, but she sidesteps answering that and brings it back to her bakery.
“You work a lot, it seems”, I say trying not to come off as judgemental. “It’s very admirable. You have incredible work ethic. But do you give yourself enough days off?”
“What do you mean by enough”, she asks.
“Any days off, I guess. Sounds like you’re working 24/7.”
Callie sets down her knife and fork and sits back on her chair, thinking about her response. She tells me that she doesn’t take days off from the bakery because she likes what she does.
“Right, but that deprives you from enjoying your prime years. You’re young, you shouldn’t be keeping yourself trapped behind an oven”, I say.
“What would you suggest I do with my free time if I gave myself more?”
I reach out my left hand and hold on to her right. “Going on dates would be fun. I mean, if I were a young, single, beautiful lady.” Shit. Maybe it’s been too long since I last flirted with someone, but I can’t bring myself to be too forward with Callie. I don’t want to jeopardize this evening by insinuating that I want to do anything more than a nice dinner. Even if I could see myself with her, I shouldn’t set either of us up for disappointment. For all I know, tonight could end badly. Or it could just end with us as friends. I have no reason to assume otherwise.
Though she blushes, I get no further response from Callie about taking some time away from the bakery to take up dating. I specifically made sure not to imply that she should date me, in case she’s not interested in me like that and just wanted to accompany a lonely guy on his supposed birthday.
We continue our meal, but our pauses for conversation are now heavily one sided on my end. I talk endlessly about the shows I’ve been watching recently on digital streaming services, some movies I’ve been dying to watch, and a lot of other unimportant nonsense that I find is boring Callie.
Turning the conversation back into a more balance back and forth, I ask Callie about the cake she made.
“You didn’t really give me much to go off, so I went for a crowd-pleaser. A tres leches cake for dos. I hope that’s alright.”
“Tres leches? Hell yeah, that’s alright! There’s no way you didn’t know that was my favorite, did you ask Taryn?”
“No. I just took a wild guess. It’s hard to hate tres leches cake. Unless you’re lactose intolerant, I suppose. You’re not, are you?”
“Nope. And hell, even if I was, I’d suffer through some irritable bowels for some cake.”
The two of us share a laugh as we finish our meals and get ready to share the cake Callie brought. Before stabbing my fork into the beautifully decorated cake, Callie stops me. She digs out a candle from her clutch purse and places it on top of the cake.
“There’s no way you’re going to have a birthday cake without blowing out your candles and making a wish first”, she insists.
With a shrug, I excuse myself to grab a lighter from the kitchen. I return quickly and light the sole candle.
“Don’t forget to make a wish”, Callie reminds me.
I blow out the candle, carefully remove the warm candle and dig into the cake. Another ‘holy shit’ escapes me after trying Callie’s cake. She giggles happily and takes her first bite. She also lets out a quiet ‘holy shit’.
“Sometimes, I forget how good my own skills are. Fuck, this is good”, she moans.
While we devour our dessert, I repeatedly look up at her to try to see whether or not I can pinpoint how much she’s enjoying this date. It’s hard to tell because of how much she’s enjoying the tres leches.
“Would you like to know what I wished for”, I ask her.
She shakes her head. “No way. I mean, I do, but you can’t tell me, otherwise it won’t come true.”
“I’d say that’s a fair point, but fact of the matter is, it already came true”, I confess. “I wished for you and here you are.”
It may not be my real birthday but that’s no reason to avoid undergoing some growth. My last relationship ended in the worst possible way a relationship could end. Financial, emotional, and professional ruin. It fucked me up, to put it lightly, and because of that, I’ve spent the last year of my life in solitude. It’s time to grow up and move on. Maybe not into a relationship, don’t want to move too fast, but some sexual contact I believe would be helpful.
Or at the very least, a kiss.
I get up from my chair and walk over to the other side of the table. Once, I’m in front of Callie, I slowly lower myself until my face is inches from hers. I lightly caress her face as I move closer to it, pressing my lips against hers. She doesn’t pull away.
Callie runs her fingers through my hair and pulls me closer to her. Without warning, she wraps her legs around my waist and her arms around my neck, completely lifting herself up from her seat. Though not a turn off, I quickly realized that Callie had not had much experience making out. I’d give her an A for effort, but as far as making out goes, the many pecks she gave me would be result in an F. It’s good for her that she has a good teacher to help her.
I held her head in place and slowly pressed my lips against hers, parting them to slide my tongue into her mouth. This caught her by surprise, but her surprise turns into delight as she allows it to happen. She starts using her astounding core strength to grind on me as she and I practice making out. I open my eyes for a moment and see her smiling ear to ear as we make out. She’s been wanting this-- needing it, even.
Best not disappoint her, then.
T
he foreplay may have gotten started, but an important choice has to be made and it’s one that is best made in silence. I have to decide whether or not we have sex on top of my apartment building where anyone could just walk in and see us going at it, just because I think it’d be romantic to have sex underneath the gorgeous blanket of stars out tonight. Or, our second option would be going back to my room and getting hot and heavy on my California King sized bed. Being as how it’s a bit windy out, I go for the bed.
I hold onto Callie’s ass and continue making out with her as I start carefully making my way through the roof, down to my apartment.
“Do you have a condom”, Callie whispers.
As we make it into my room, I lay her carefully on my bed while I search my nightstand for a condom.
“Right here”, I answer.
“In that case…”
Callie playfully slides off the straps of her black dress until the only thing holding up her outfit are her nipples. Even if it’s only for a moment. Callie’s dress falls to the floor, revealing that she had been going commando this entire time.
“I just wanted to be ready in case anything happened”, she coyly explains. “Ready for you, Declan.”
Instead of wasting any more time gawking at her, I undress quickly while trying to remain calm so as to not look too desperate. She’s already completely naked but gets extremely excited when she sees me down to my boxers and nothing else.
“Can you take your underwear off really slowly”, she asks.
Happy to oblige, I take my time sliding my underwear off, making sure to drag the waistband down the length of my shaft until it’s in full view. She gasps when my cock bounces out of my boxers and points straight ahead. I tear open the condom wrapper but Callie stops me again.
“Hold on. I want to get a better look.”
Carrie curls her finger at me, asking me to get near her. She places both of her hands on my waist and studies my cock as if it was a pastry she was about to decorate. Her face gets closer and closer as she moves around it, comparing it’s massive size to parts of her; her forearm, her entire face, her neck.
“It’s so big. Do you think I can handle it?”
“I’d like to find out”, I whisper.
She suddenly grasps my cock with a fierce grip and lightly kisses the head.
“Let’s see what I can do with mouth, then we’ll take a trip down South. How’s that sound”, she asks with a mischievous look on her face.
“Sounds perfect”, I tell her.
Her lips envelop the head of my cock and slowly travel farther down the shaft. She chokes halfway and starts again, sliding her tongue back and forth against the underside of my cock. We didn’t get a chance to have a discussion on either of our sexual histories but I’d be completely taken aback if Callie were to tell me that this was the first time she’d ever had a dick in her mouth, because she is working my crank like nobody ever had before. I’ve watched porn where the pornstars are doing the technique Callie is incorporating and I’ve always been jealous of the guys those dicks belonged to. And now I get to experience it myself. It is a dream. More than a dream, calling it that doesn’t do it justice. Each time her tongue travels down my shaft, waves of goosebumps are sent to the farthest points of my bdoy.
She looks up at me and even though she has a mouth stuffed with dick, manages to make out a smile. Callie slobbers all over my cock and jerks me off with both hands, getting ready for a load to shoot out of me and land in her open mouth. The bouncing sensation of an imminent orgasm starts hitting me but instead of exploding all over Callie, I stop her and ask her to get on the bed, on all fours.
While she gets in position, I put on the condom and ready myself to enter her. Before making a move, I stare in awe at her beautifully round ass. I reeled back and landed one stinging slap on one of her delicate butt cheeks. A small, eager scream escaped from her and was followed by a moan, the sound of desire. I slap her ass on the same spot three more times, leaving a bright red hand print, marking her as mine for the time being.
“You like that, Callie?’
She’s breathing heavily now but is able to nod her head. Not only that, but she positions herself into a more extreme stance. Instead of being on all fours, she places her hands behind her back, her face flat on the bed, and her ass high in the air.
“Give me everything you have”, she begs.
I place both hands on her ass and spread her cheeks. Her sopping wet womanhood makes a perfect entrance. Slick. Tight. Deliciously noisy as my protected member enters her. Her pussy welcomes me with a warm, loving embrace. The deeper into her body I went, the more I could feel her pussy tightening, hugging my dick almost as if she’s trying to crush it. But the more pressure I feel, the harder and deeper I want to fuck her.
She gasps in surprise and pain once my cock reaches Callie’s limit.
“Is that all you can take”, I ask.
“Yeah… That’s it…”, she says breathlessly.
“Perfect. That’s all there is.”
Callie sighs, relieved that there wasn’t more cock to take into her tight, petite body. But all she’s done so far is test her limits. She hasn’t even experience the intense fucking I can deliver. I bend over and kiss her back, then warning her to brace herself. I hold her torso down with one hand and then begin fucking Callie with all of my might. Mercilessly. I fuck her as hard as I could possibly fuck a person.
Much to my surprise, not only is she taking the hard thrusts with gusto, but she starts begging for me to fuck her even harder than I already am. With both hands around her waist, I bury my dick in her pussy and start delivering short, rapid fire thrusts whilst also digging deeper and deeper. This is perfect for us both. I’m at the verge of shooting a load and I can feel her on the same path of climaxing. Hell, I can hear her about to climax. Callie’s screams of passion are only slightly muffled by the loud clapping of our bodies being slammed against each other. My ecstatic moans followed soon after. I felt myself inching closer to the big finale, making me slow down, but Callie isn’t quite there so she starts moving her hips, making her ass bounce against me until it finally happens. She squeezes my cock tight with her pussy and screams as if she’s being murdered while I shoot numerous loads into the condom I’m wearing.
“Keep fucking me”, Callie begs me. “Please, don’t stop.”
“I have to get a different condom. I kinda ruined this one”, I explain as I slide out of her. Upon looking down at my cock, my heart sinks to the empty depths of my core.
The condom is leaking.
An unspeakable terror. Anyone’s worst fear. Some would say that it’s a blessing in disguise, but whoever says that is a fool who secretly wanted to get pregnant or an asinine idiot in total denial of the horrid situation they’re in.
“Fuck”, I shout. “The condom tore. Jesus Christ, I’m so sorry!”
Plan B. I have to head down to the pharmacy and buy Callie some Plan B. But what pharmacy is open this late at night, holy fuck, I am fucked, I cannot get somebody pregnant. I’m in the midst of a complete turnaround in life, I cannot have it ruined by knocking somebody up.
“Declan, it’s alright”, she nonchalantly states.
Alright? Alright? How in the everloving hell could that be alright? I’m sweating bullets and she’s laying down on the bed calm as ever, as if I hadn’t just announced to her that the jizz that shot out of me actually went inside of her and wasn’t stopped by a thin wall of latex.
“How can you be so calm, Callie?!”
“I’m on the pill. Now will you relax?”
And so begins the barrage of stammers. “The pill? The contraceptive pill… You… So… You’re on the… Okay... Not pregnant… Good. Good. I… Holy shit, that’s great.”
“Want to lie down for a sec”, she asks.
I take a deep breath and lay down next to her, quietly laughing, relieved of the massive bullet I just dodged. Callie asks me again if I’m sure I’m okay, and I reassure her that I
just had a bit of a panic attack that came and went.
“Would you like to cuddle then? Maybe fall asleep on your monster sized bed?”
“Sure”, I answer.
Callie scoots up next to me facing away from me, asking to be spooned. I wrap my body around hers, still delighted that I don’t have to deal with the consequences of accidentally shooting a load into someone, unprotected. My heartbeat now is just as intense as it was while Callie and I were fucking.
“So all things considered, how would you rate this birthday”, Callie asks.
Two Bad Bosses_An MFM Menage Romance Page 33
