Chapter 5
by JennCarcione
What's next?
Tell John the date is over
I need to play this right. If I give him everything I have right now, I will never get enough money to stop the foreclosure and save my family home. If I give him my all, I will get nothing out of it. He'll accomplish his goal, making my box less desirable, therefore, less valuable. He received a tease of what I have, and if I leave now, he'll lust me more. Remember, the goal is to pay bills, not fulfill the sexual fantasies of an old man. I look him in the eyes chuckle, "It's our first date, John. I don't put out on a first date."
His face immediately melted into a look of disappointment, then anger. He responds, "Baby girl, you know you made me excited. You can't leave me like this. You owe me."
He's right. I was taught to never lead a man on and leave him disappointed. If he's angry, he might never call me again. All I would have gotten out of tonight is a necklace and a free meal, neither of which will mean anything if my parents loose the house. I respond, "I am sorry, I have an early appointment tomorrow morning to fix my financial situation. If I miss the appointment, I'll never get the funds to save my moms house."
John places his hand on his chin while he thinks for a moment. He smiles as he says, "I have a proposition for you. I'll have my driver drop you off at your house in Queens as long as we can play in the back of my car. When we arrive at your place, I'll give you $100 - $1,000, based on how much fun we have. This will be the most profitable fun-hour of your entire life."
John makes a compelling point. I can tease him, not give him my all, earn money and get home. Win-win-win-win. I nod my head.
As we leave the restaurant, John places his long black Burberry Trench Coat around my shoulders and says, "It's late December in NYC. You should know better then to go out without a coat.
He's right and I respect the offer. I smile at the polite gesture, possibly a bit too soon. Walking next to me, he slides his hand inside the jack around my waist and quickly begins lowering his hand towards my butt. When he gets there, he gives it a quick squeeze, feels around the entire butt and continues to lower his hand. I know I should feel embarrassed, but the only thought in my head is if my butt is too small. His hands continue to lower until he reaches the hem of my dress, then he quickly lifts it up so that my entire dress is above my waist, hidden only by his trench coat. As we continue to walk to the curb, he begins exploring my now nude butt, protected only by my skimpy thing.
When we get to the curb, we are greeting by his driver, standing in front of a new, polished SUV. John removes his hand from my butt. I fix my dress before accepting his hand into the SUV.
John enters the SUV from the other side of the car and closes the door. His driver says, "Good evening Miss Jenny Mr. Jefferies, You both look fantastic tonight. Would you like me to take you to the estate, the loft or another destination?"
John replies, "Forest Hills, Queens, and take your time." John places his right hand on my left leg. I get a quick chill up my body as his old, cold had touches my skin. John begins rubbing up and down my leg. His hand rides up my golden leg and begins to caress the soft yet firm skin on my inner thigh. With his left hand, he moves my left hand from his knee to his crotch. He places his large, masculine hand over mine. He curls my tiny, soft hands around his shaft and begins stroking it through his pants. After a few moments, he removes his hand from mine. I keep stroking like he just taught me. He nibbles on my earlobe and whispers, "good job baby girl."
His complement makes me smile. He continues to rub, brush, squeeze and own my leg. His hand comes extremely close to my now extremely wet pussy. I subconsciously thrust my hips forward, hoping to feel his masculine fingers. My special place has this dire urge to feel his hands.
John slips his fingers over my panties, lowers his pointer finger under the cotton and touches my tiny, tight clit. The feel of his forceful hand excites me. He begins to wiggle his finger around my clit, further turning me on. Without notice, he takes his middle finger and pushes it all the way inside my pussy. I thrust my hips into his finger and moan, as I squeeze his cock. He whispers, " Tell me you love this baby girl."
Without thinking, I respond, "I love you daddy." Oopsie. That is NOT what he asked me to say. How embarrassing. I hope he didn't tear or notice. I look at his eyes and he gives me a confused look of shock and appreciation. John replies, "Prove it." He unzips his pants, puts his spare hand in his pants and pulls out his massive cock.
I was expecting it to be big, but this thing is huge. It is in fact at least 7 inches long and as thick as a cucumber. Its the perfect shape and texture. It's absolutely beautiful. I stare at it for what feels like 15 seconds. John looks me in the eyes, places his thumb in my mouth, circles it around my tongue and says, "Suck it baby girl."
I've never given a blowjob in my entire life. I don't want him to think I'm a prude or unexperienced, but I don't know how to do it well. I've watched a few porno's when I was considering giving my ex-boyfriend one, but I never had one in my mouth IRL. What If I am bad at it? What if it doesn't fit in my mouth? I respond, "I want to but I'm not sure I will do it right."
John begins pumping his thumb in and out of my mouth and says, "you'll do just fine baby girl." He continues pushing his thumb in and out of my mouth, staring in my eyes. I presume this is how he wants it done on his penis. He moves his fingers from my mouth to the back of my head and nudges my face towards is erect cock. As he pushes my head towards his dick I think, "I guess I'm doing this." When my mouth touch the head of his dick, I begin to part my tiny Asian lips. He smiles and pushes his hard cock between my lips and inside my virgin mouth. He pumps it in my face deeper and deeper until the head of his cock is entirely covered by my mouth. It barely fits between my tiny, thick lips, but he forces it in. I begin to circle my tongue around the head of his cock like I saw in the video's. Meanwhile, I take my tiny, soft hands and begin massaging his hairy balls. He groans while thrusting his thick, hard cock deeper down my throat. I almost gage from its depth and girth as I can barely breath, but I hold it together.
He now has both hands on the back of my head and is completely fucking my face. With each thrust, he pushes his cock deeper and deeper down my throat. His thick cock is filling my mouth and pumping through my tonsils. His hands are continuing to control my head, using my face to fuck his massive member. I can barely breath as he shoves it down my throat, but hold my thoughts inside.
John moans, "Mmmmmm, good job baby girl. Keep up the good work on daddy's dick." The words of encouragement make me feel good. I think I'm starting to get the hang of it. I begin to taste a warm, sticky substance and recognize it as pre-cum. I must be doing it okay. Moments later, I feel a rush of thick, white cum filling my throat, then another, then another. I **** a little bit as I pull my head out of his cock. He pushes his cock back deep down my throat and shoots a few loads, which make me gag. He pulls out and pumps a shot which lands my face and a final blob on my hair. Just as I start to clean up, he pulls into the driveway of my family house. He hands me $1,000 and says, "I'm sure we can come to an arrangement so that you can keep this house. I'll give you $1,000 a week if you please me when I desire. I'll also give you a budget."
What do you do.
1) Accept the sugar baby offer
2) Deny the sugar baby offer
3) Make a counteroffer
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for Money
Medical debt caused me to do unspeakable things
At 20 years old, I was to drop out of college to cover my parents debt. I resort to meeting people and fulfilling their sexual needs to keep their home from foreclosure.
Updated on Feb 18, 2025
by JennCarcione
Created on Dec 25, 2024
by JennCarcione
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