My Daddy, My Pimp Ch. 01: Introductions

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My Daddy, My Pimp: Introductions (Part 1)

I wasn’t sure what to expect when Daddy first snooped on my computer and found my ad on a website advertising for sugar daddies. Can you ground an 18-year-old for life? Could he really begrudge me trying to come up with some money so I wouldn’t have to work my first semester at college? And what the fuck was he doing on my computer anyway?!? I only had a couple of weeks remaining until I left for Cal– I ALMOST made it.

But when I came home from the gym mid-afternoon, there he was: sitting at my computer, browser open to my profile, showing a picture of me bent over, generous ass exposed, my face to the side of my leg, smiling cheerfully. The description, “starving coed” advertising for a “discrete financial arrangement” with a “generous older man,” glared brightly underneath the photo. It was indisputably me—I would have lied my slutty little ass off if I could have. But he wasn’t looking at the screen, just at me standing in the doorway, his face impassive, unreadable. I opened my mouth, prepared to defend my privacy with all the righteous indignation I could muster, when he cut me off and his first words rendered me totally speechless:

“I’m not ashamed of having raised a whore; I’m ashamed of raising a slut with such poor business sense.”

I froze, paralyzed by the surreal sound of that sentence, not sure which part of it I found most offensive. “Daddy…” I started, unsure where I was going. My daddy has always been a ‘no bullshit’ sort of guy. But this was blunt by even his standards.

“Sit down, Kitten. You look like you’re about ready to collapse in shock anyway.”

I dropped with a huff on the corner of my childhood bed, my legs giving way, all the fight drained out of me.

“Look, honey, I know what you’re trying to do here, so you can skip all the rationalizations. You need money that we don’t have. I get it. You don’t want to be stuck with student loans for the rest of your life and you don’t want to have to work 40 hours a week for your first semester at college. You don’t want to be slinging burgers at some crappy fast food place to make ends meet, and be crippled by student loans for a decade after graduation. And since the fact that you got into Berkeley in the first place is amazing to both of us, you don’t want to be so worn thin that you flunk out freshman year. This is the best opportunity you’ve got to get out of this shitty neighborhood and not end up doing blue collar work like me and your brother. I get it, baby girl. I really do. But you’re going about this all wrong.”

“Daddy…” I began again. Christ, was that all I had in me to say?

“Hear me out. First off, your way is entirely unsafe.” He swiveled the chair around and pointed at the screen. “You’re advertising here that you’re ‘willing to travel.’ So you’re going to let these strange men fly you off to their home cities? What if you feel threatened? What if they beat you up? The guys on these websites aren’t going to be the highest quality, kid—they might want all sorts of things other than an easy fuck. Anything could go wrong and you’d have no one to call.”

“I was going to tell Carla… you know, call and check in,” I interjected feebly.

“And your best friend from high school is going to fly out immediately and fend off the creepers? You’d be chopped into little pieces in a trunk before she got on the plane.”

“And it wouldn’t be like that, Daddy! Some of these guys say they’ll help you out with rent or pay your tuition. One of them wanted to take me on a Caribbean cruise! My friend, Lacy, just had to dress up and be a dinner date for fancy political dinners. It would be just like that old movie! The one with the red head?”

Daddy shook his head, exasperated, and groaned. “Pretty Woman. You’re thinking it would be like Pretty Woman. Sweet Jesus, you’re a babe in the woods. You have no idea.”

“It’s a high class website, Daddy! I wouldn’t even have to do it very often because I could charge a lot of money for just the once!”

“Helen, five hundred dollars a weekend sounds like a lot to you, I know. And for one customer, it is, but you’d be better off selling yourself to more customers, at a lower price. You have wide appeal. With your body… honestly, you could have tons of men willing to pay for it locally, if the price was more reasonable. And then you wouldn’t have to travel somewhere and meet up with potential axe murderers.”

I had no idea what to say. His voice was calm, rational, almost convincing. Of all the reactions I had been expecting, this was not one of them. He looked at me levelly, uncomfortably holding my gaze and daring me to break it.

“Sweetie, there are better ways to do this.”

As Daddy and I stood on the bağdat caddesi escort doorstep, ringing the bell, I looked down at myself. My bare legs and towering heels were almost invisible under the swell of my giant tits, which were braless inside the white, wife-beater tank that was fighting a losing battle to contain them. The outline of my nipples was obvious under the light-colored fabric. The short jean skirt that completed the outfit made me more street walker and less high-priced courtesan, but Daddy had been so sure this was the way to go.

The building we were outside of was really not what I had been expecting either. It was a non-descript, square, brick monstrosity, decorated with a single flashing neon sign that just said “Jimmy’s.” There was no parking lot, just meter parking on an unlit side street in one of the shadier areas outside of L.A. The road was lined with beat up muscle cars and old sedans.

Well, this is a far cry from my daydreams of the Marriott, I thought nervously, as I shifted my weight from leg to leg, painfully aware of the visibility of my rigid nipples in the cool night air.

When the door swung open, we were greeted by a greying, mustached man, heavy through the shoulders and thick through the middle, who looked about ten years older than my dad. After giving every inch of me an appreciative appraisal, he squinted suspiciously at Daddy, before recognition widened his eyes.

“Alex?!?” he asked, swinging the door wide, and ushering us in. “Jesus, I haven’t seen you in twenty years! Didn’t even recognize you!” He clapped Daddy affectionately on the shoulder. “And up to your old tricks, I see. Who is this lovely piece of ass?”

“Good to see you too, Jimmy. And this lovely piece of ass is my 18-year-old daughter, Helen. I’m her…” Daddy paused, searching for the right word, and then said with heavy emphasis. “I’m her escort for the evening.”

Jimmy’s eyebrows shot up. “An…er… escort for your own kid, huh? Well, that’s new. But you always were a filthy bastard. Last time I saw you, you were just a customer here. But you were a regular and I never forget a face.”

As my eyes adjusted to the low lighting, I realized that Jimmy’s place was far more disreputable and squalid than even its exterior would have suggested. The dark room was only dimly lit with florescent signs, and clouded with a thick haze of cigarette smoke, suggesting that there were some venues where the city’s firm “no smoking” policy were null and void. At one end of the room there was a mostly abandoned stretch of bar, a bored looking bartender lazily wiping down the counter. The rest of the place was filled with leather booths tucked up against the walls, and was only operating at about fifty percent capacity. The men sitting at the booths were sometimes alone, often accompanied by scantily-clad women either too young or too pretty to be their unpaid dates. One older man near the back was mindlessly groping the ample cleavage of a voluptuous girl near my own age while she drank a Stag and giggled. Several of the men looked up and watched the interaction between Jimmy, Daddy, and me with growing interest.

Now it was Daddy’s turn to look unexpectedly awkward. “Yeah, it’s been a long time. Sorry I haven’t dropped in. Ended up with a divorce and a couple of kids to raise. You know how it is. But at least I brought you a little something,” Daddy said, nodding in my direction. Something about how the two men were talking about me as if I wasn’t there, referring to me like they were selling a delicious candy door-to-door, made me shiver.

“In my business, Alex, you never look a gift horse in the mouth. When you bring me goods like this, you’re welcome back any time. Mind if I check out the merchandise?”

Daddy placed his hand on my low back, and shoved me forward. I lost my balance in the ridiculous heels and then straightened myself, pulling my shoulders back and pushing my assets forward, so that Jimmy could get a good look. Jimmy clapped his hands my shoulders and raked his eyes up and down over my body, stopping a little too long on my enormous rack. He spun me around and I stiffened at his hands slid up my short skirt to fondle my ass. I felt like a Thoroughbred being evaluated for sale on the open market.

Next, he’s going to pry open my mouth and check out the condition of my teeth.

“Little thing. Probably only about 5’2″ without these fucking stilts. We got some guys that like that. And tight. Tight like a gymnast,” Jimmy muttered to himself, taking a mental tally of me, as he ran his hands over my stomach. “Good hair. We don’t have enough brunettes around here, and I’m tired of fucking girls with bad bleach jobs. Natural is in. Clients like natural. Good thick thighs. Big bahçelievler escort ass. Mind if I check out these tits, Alex? Just to make sure they are what the customers are looking for?” he asked with a wink, as he spun me back around.

“You can play with her tits till your heart’s delight… but you’ll pay $5 bucks for them, just like everyone else.”

Jimmy laughed heartily, and he fished a crumpled bill from his pockets. “I admire your entrepreneurial spirit.”

“Come here, Helen, and let the nice man have a look at your fat titties,” Daddy said, as he grabbed the bottom of my tank top. Sweet Jesus, did my daddy just say “fat titties?” This was obviously a side of his personality I didn’t know. Maybe he was just playing a character? One that fit the ambiance?

I was now the center of attention. As most of the men in the bar gazed at me approvingly, Daddy pulled my tank up to my armpits, freeing my tits, which sprang forward after their confinement into Jimmy’s old, gnarled hands. He jiggled them, and ran his thumbs across my nipples, which hardened and erected under his touch. A single, helpless moan escaped me, oblivious to the fact that I was standing with my tits exposed in a filthy bar. Without warning, he pressed them both together, and leaned over, sucking both my nipples at once into his hard mouth. I groaned and arched my back.

“I think she’s gonna like this, Alex. Any ground rules before we start the party?” Jimmy’s eyes were still on me, devouring my hard nipples, as he continued to grope my DD-cups.

“Mmm… for now, hand jobs, blow jobs, and anal. We got her on the pill a couple days ago, but I’m not sure it’s taken effect and I don’t want her knocked up.” As he said this, Daddy stepped behind me, slipped his hands under my heavy boobs, jiggled them, and lifted them up for Jimmy’s tongue to flick over.

“Anal?” I asked nervously, but neither of the men responded, as they manhandled my breasts. All this was moving a little fast, and I had the distinct feeling that I was now in a car with no brakes. I was a long way from a virgin—I’d had boyfriends since sophomore year. But the only thing that had been in that particular hole was the single finger of a drunk frat boy a few months ago.

Jimmy took my hand gently and led me across the room to a dirty bench, where he gestured for me to sit next to him. Daddy pulled up a chair across from us, crossed his legs, and leaned back. Like a patient tutor, Jimmy took the hand he had been holding and pressed it to his crotch.

“Go ahead, Helen. Take Daddy’s friend’s cock out of his pants.” Daddy nodded nonchalantly at his friend. “This will be another $20, Jimmy.”

I ran my hands over the old man’s crotch, grazing over what felt like a fairly massive bulge, while Daddy watched approvingly. As I unzipped his pants, I noticed several of the men in the bar had gathered around to watch the scene, and they were rubbing conspicuous bulges of their own as they watched me pull Jimmy’s length free. For an old man, Jimmy had an excellent piece of equipment—it’s girth more remarkable than its length, which was about seven inches long. Hesitantly, I started to stroke his cock, unable to get my tiny fingers to touch around its width. Its skin was impossibly silky, and it twitched in my grasp. Jimmy continued to tweak and twist my nipples gently, and I gradually became aware that that I was making small, whimpering sounds, high in my throat. I could feel Daddy’s eyes on me, and even more than Jimmy’s impressive dick, this made me feel shamefully, horribly turned on.

Daddy continued to watch us intently. “That’s right, girl. You like it when Daddy shares you with his friends?” Daddy said huskily. His calm demeanor still remained, but I couldn’t help but think something had changed in the tone of his voice.

Jimmy pulled me onto his lap, pushed my skirt up around my waist, and pulled down my carefully selected black, lacy panties somewhat unceremoniously. “Spread your legs, girl. Show our customers your tight little hole,” Jimmy whispered into my ear, pulling my knees apart so that the gathering circle of men could get a better look at the interior of my pink, wet pussy. I could feel Jimmy’s hardness pressing against the crack of my ass, and I tried not to flinch, knowing what was in store for me. He spit on his hand, reached down, and started to massage the tight, puckered opening of my asshole, until it yielded and gave way to a finger.

“Pull your pussy lips apart so your Daddy can watch, while I finger your little asshole, girl,” Jimmy ordered. Nervously, I met Daddy’s eyes. His breathing seemed quick now. Holding his gaze, I slowly reached down slowly and opened up my pussy with two fingers, so Daddy could see the inside of my slit while bahçeşehir escort his friend’s fingers plunged in and out of my asshole. Daddy’s eyes on me, the degradation of an old man’s finger in my ass, made my heart pound faster and faster. I whimpered as Jimmy inserted a second finger, stretching me open in front of my daddy.

“Mind if I stick my cock in your little girl’s ass, Alex?”

“Fifty bucks, please,” Daddy snapped, his voice sharp, curt, his eyes never leaving my open hole and exposed tits.

“Daddy, I don’t know if I can. He’s really big and I…” I protested weakly. But neither man seemed to hear or care. The reality of my situation descended on me with an almost audible mental crash.

What kind of shithole was this place? Where an old man could just shove his filthy cock in a teenage girl’s virgin asshole for fifty bucks in front of everyone?

With my legs spread, and Daddy watching closely, Jimmy pressed the head of his giant cock up against my asshole. I tried to squirm away, but Jimmy had me firmly around the waist. Much to my embarrassment, my wet pussy had lubricated my tight backside pretty well, and I felt my little asshole stretch around the tip of the invading organ. The shock and pain were intense and brought involuntary tears to my eyes, but Jimmy grabbed my hips and held me down onto his impaling member, as I tried to wiggle away. Jimmy reached down and started to rub my clit, whispering “that’s a good girl… that’s a sweet little whore…I’m going to make you come with my dick deep in your ass.” I groaned helplessly in spite of the pain, sure I would eventually do what he wanted, and started to squeeze my own tits as I rocked back and forth on the iron buried in my ass.

“That’s it, darling,” Daddy said urgently. “Now slide your little asshole up and down on Jimmy’s cock. Keep that asshole stretched open around that fat cock. Do you like it when Daddy loans you out to all his friends, so that they can use your sweet little holes? When he sells your little butthole for cheap? So they can use your little asshole to come in? There you go, honey. Work your asshole up and down. You’ve got to work out some cum right into your ass if you want to get paid.” Daddy had taken out his phone and seemed to be filming a close up of my wet, open pussy and the enormous cock sliding in and out of my asshole.

I was shocked to see the outline of Daddy’s own very hard shaft through his pants. Is it possible he was enjoying this? Watching his young daughter be fucked by a man over twice her age?

Despite my disorientation from the array of intense sensations, it had not escaped my notice that almost a dozen men had circled around me and Jimmy. A few of them were just nursing drinks and enjoying the free show, but several had taken out their own cocks and were slowly jerking them. “Yeah, girl, bounce that fat ass on his cock,” a man with his dick out shouted encouragingly.

As I writhed, my virgin asshole impaled on Jimmy’s rod, they would reach out and pinch my nipples and squeeze my giant tits appreciatively as they bounced up and down. A skinny man with glasses leaned over and sucked hungrily at one of my nipples, forcefully beating his shaft with his other hand. I felt something prod my cheek and had no time to react as someone unleashed a load of thick cum on my face, which dribbled down into my open, panting mouth. The guy on the other side, a young man closer to my own age quickly stepped forward and shot a thick load all over my tits with a guttural groan. White drops of semen slid down my breasts, collecting in thick strands dripping off my erect nipples. Another customer rubbed the sticky cum into my sensitive nipples, as I ground my ass into Jimmy’s lap.

“Oh, fuck, Alex,” Jimmy groaned. “Her asshole is so fucking tight. I’m gonna dump a load right in her tight, little butt. Seriously, dude, you should try this thing. If I were you, I’d be using this little asshole any chance I got.”

Jimmy’s filthy suggestion triggered my first orgasm of the night, and I moaned helplessly, rocking back and forth and looking at my daddy as I came all over his old friend’s cock. I’d never felt so filthy, vulnerable, and exposed in my whole life. My asshole locked down on Jimmy, and I could feel his dick contracting powerfully, just as he shot a stream after stream of cum into my tender, tight hole. Jimmy squeezed my tits hard as he pumped his load into me, Daddy filming his giant member as it spasmed in my ass. Breathing hard, I collapsed backwards onto Jimmy’s chest. I could feel Jimmy’s hot, sticky cum leaking out of my open asshole, still stretched wide around his cock.

My daddy stood up and smiled down at me. As he tucked his phone away into his pocket, he ran his hands through my sweaty hair, pushing it back from my flushed face. “You’re such a good baby whore, Helen, taking a big cock like that right in your asshole. But I hope you’re not tired. You’ve got a lot more to do tonight…”

He looked up at my audience, many of them tucking away their own spent members. “And if you came on her, you owe me another ten bucks!” he barked.

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