My Wife's Fucked up Family Pt. 02: Ho Daddy

Story Info
Charles serves his kinky sister-in-law and husband.
3.9k words
4.53
19.7k
17

Part 2 of the 6 part series

Updated 06/11/2023
Created 12/04/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
MVP6
MVP6
701 Followers

(This story is part of a series. I strongly advise that you read My Wife's Fucked up Family - Part 1 first.)

The following Friday after the holiday party, I was making the forty-five minute drive to Calla and Cadence's home. I had to get there on time so I wouldn't disappoint them. It was the punishment the group decided on for me having sex with my wife's sister Lily and her husband Rod.

I had little idea what they had planned for me, other than my wife loaned out my mouth to them, and their nicknames on the placecards had been Ho Daddy and Burrito Grande. Calla had said the nicknames were related to their particular kink.

From my experience with Rod, I learned that my love of pleasuring others orally extends to men as well as to women, but when I think about a man's junk it turns me off.

Calla doesn't do that much for me sexually either, as she's the only one of the five sisters who isn't attractive. I mean, her body's fine but her face could stop a truck.

Cadence was rumored to have a cock which rivaled Rod's in size. Also, his ancestry was Mexican so it made sense that he was Burrito Grande. Just why Calla would be called Ho Daddy made no sense.

I got there just before lunch, Put my bags in the guest bedroom, and was treated to a fine lunch. We all sat around the kitchen table eating and talking casually as if I wasn't about to be the sexual main course.

When lunch was over Cadence took me into the bathroom instructing me to take a bath. Afterwards he shaved off all my body hair.

At first I objected stating that only my mouth was on the line here. But Calla produced a video from that night proving that Rose said I had to cooperate in all the preparations. I didn't even know someone had taken video.

While he was preparing me he removed all his clothing as well, revealing that he too was hairless. His penis was dark and thick and uncut, about five inches soft.

Cadence pampered me and groomed me and treated me like I was the most special person. I could really get off on all the attention. He said we were getting ourselves ready for Ho Daddy, who liked us that way. I supposed that was her kink - every couple in the group, allegedly, possessed a unique kink.

Since I was to be loaned out to all the couples I would learn each and every one of their kinks soon enough.

At one point I was lying on my stomach while he plucked the last stubborn hairs he couldn't get with a razor from around my anus. Kneeling next to me, his package incidentally fell into my open palm so I cupped it. It gave me a secret thrill to feel it and to know he enjoyed my touch.

When we were done in the bathroom Cadence disappeared somewhere but Calla took over. I could see she was in the process of changing from her everyday clothes into something else. She took me to the bedroom where she rummaged through a number of sexy outfits finding just the right one.

She chose a red lacy bra, matching crotchless panties, a black leather mini skirt with leopard trim, fishnet thigh highs and hooker shoes. I was ready to take my turn pampering her and dressing her in the outrageous getup, but she walked out the door casually saying, "Put them on and meet us in the living room." My mouth fell open in alarm, but she never stopped to notice or care.

When I was done, with my short hair, I looked like a shamed prostitute in the gaudy combo.

Sucking up some courage I entered the living room to find Calla dressed like a 1940's gangster-pimp wearing baggy black dress pants, jacket, and purple fedora with leopard trim to match mine.

A moment later, Cadence appeared wearing the identical ensemble as myself, except he had a long brunette wig: much like the blonde one Calla was now holding out to me.

Next, they did my makeup shooting for a cheap whore theme. The effect worked perfectly.

Applying the finishing touches, Ho Daddy snatched up her car keys announcing we were going for a drive. I knew they owned a 1940s Packard Sedan, and coupled with these outfits, I realized they were wholly committed to this theme as much more than a one night thing - kinky.

I was glad for the tinted windows as we drove downtown. We arrived in front of a decrepit movie theatre where Calla asked me to inquire about tickets at the booth.

I would be mortified to be seen in public - to watch a whole movie dressed like this.

Stepping out, I caught the eye of a couple walking by on the busy sidewalk, who stared lecherously, while I hid my eyes.

I was all nerves while the young guy was telling me that the show played on a continuous loop and was fourteen dollars a pop. He asked if I wanted a ticket but I had no cash and no credit cards. I kept tugging on my skirt, hoping to hide the tops of my stockings from passersby, but it was no use.

I returned to Calla and Cadence in the purple pimp car only to discover they had locked me out. Calla slipped a note out the window with an address to a swanky hotel on it, saying, "Get there as soon as you can. The fun will be waiting on you."

As they sped off I looked around, noticing I was in the red light district. I appeared to fit in quite well among the hookers and johns.

The address was several miles away, on the other side of a bad part of town. I couldn't walk through that locale as it was much worse than the seedy neighborhood I found myself in now. I started asking guys if they would give me a ride but they all assumed "a ride" meant something else.

Finally, spying a policeman in an unmarked car, I begged him to take me there and he agreed. He drove a few blocks while I explained, totally embarrassed, that I wasn't a prostitute. Pulling into an alley he unceremoniously unzipped his pants to tug an ugly crepey cock through the fly.

I looked him over in disbelief, only to discern that he wasn't a cop at all. Just a john in a costume with a fantasy. Also, I should have noticed before, but he was kinda young to be the police.

I begged for the ride but he refused, saying he wanted his cock sucked. Outside his car there were bars on all the doors and windows and plenty of bullet holes in various objects: I wasn't going to get out of the car and he wasn't going to budge without that blowjob.

Going into the night I knew I would be serving Calla and Cadence. I had mixed emotions about that, but they were family and this was a complete stranger. The idea of sucking a stranger's dick was distressing.

He insisted on getting the police discount, which meant free, but that would do me no good. I negotiated up to fifteen dollars and a ride back to Hookers Row, but it wasn't going to be enough for a taxi. Repeatedly he insisted that I would have to swallow too. I lied, telling him I would, but planned to spit it out anyway.

I stuck the cash in my bra, then leaning across I took his unsightly member into my mouth, sucking with all the gusto I could manage - to make it quick.

He didn't smell or taste bad and when it grew to its full size it fit pretty nicely. My 'cop' must have been the most verbal of all men who have received a blowjob of all time. He spewed a litany of, "That's great! Keep doing that. Your tongue feels so good. I love it. This is the best ever. Take me in your throat. You're gonna swallow, right? I'm gonna blow. Here it comes. Here it comes!"

All the while his hands pushed my head up and down in time with my bobbing. It was cute how enthusiastic he was and how much he enjoyed my mouth. He was just a kid of nineteen or so, and I started to like him, and feel like I wanted to make it good for him.

When he started to proclaim that he was due to cum I squeezed his balls to stimulate the flow of cum and mumbled, "Give it to me. Give me your cum." I'm sure he couldn't understand my words but surely the tone of voice conveyed my meaning.

He held me down, shooting a month's supply of slime between my very giving, cherry-red lips. I think his unit pulsed twenty times, delivering his load into me.

When he let go I pulled off slowly with a tight seal, skimming every remnant from his cum soaked pole. My mouth disconnected with a "pop!"

His head was thrown back in ecstasy. I watched him come down from his orgasmic high, relishing in the pleasure I gave him. Over the course of several minutes I contentedly observed his heavy breathing returned to normal and he opened his eyes.

When he came back to Earth he asked me if I swallowed. There had been plenty of opportunity to spit while he was lost in his delirium. In answer, I smirked widely, then opened my mouth to show him the lake of spooge I'd been retaining. I made a big show of swallowing then licked my lips seductively. I even bent down one last time to suck an errant drop that lingered on his slit.

On the drive back he told me it was his first BJ: his first sex of any kind. It felt amazing to have made this kid feel so good.

I worried about this untainted youngster frequenting prostitutes so I warned him away and admitted again that I was not a lady of the night. I made no attempt to disguise my voice but he didn't seem to notice I was a man. Sometimes telemarketers mistake me for a woman so it might be me.

He was in so much awe he asked for my number. He said he wanted to take me out for ice cream and a movie. How quaint. When I declined he insisted on tipping me. Which meant now I had enough for a cab. And it just goes to show, that any job you have to do, is worth doing good.

I was knocking on room 222 twenty minutes later. It was a perplexity when instead of Calla or Cadence opening the door my wife Rose answered it. It was a greater surprise when all four couples were in the room too.

They had decided that since I was a whore and had to do whatever Ho Daddy told me, that as long as they paid Calla, it wouldn't count toward my debt, and I would still have to serve each couple on their appointed weekend.

Their plan was for me to wait on the group while they played a game of Monopoly. Then they would 'buy' amusements from me with Monopoly money, which I would turn over to my pimp.

However, it didn't go according to plan. Two hours later Cadence had won every dollar in the game and more than one sore loser went home unsatisfied and complaining. That left me, Calla, and Cadence alone again.

Trying to stay true to character they debated if one of Ho Daddies' whores could buy the services of another whore. In the end, since Cadence (Also her hooker name) had not earned her money turning tricks, it was allowed.

Cadence paid me a blue fifty dollar bill for a suck job, then relaxed in an easy chair, motioning for me to kneel between his legs. Once there we fell into our roles.

Cadence, the prostitute,started by hugging my head close to her crotch while fondling my ass through the leather skirt. I could feel a lump below his skirt. "Oh Honey, I've wanted you since that first day I saw you walking by my corner. You got a fine ass the way you strut dat for all the johns. Tell me you want to suck my cunt and clit."

He was a great actor and for a second I wondered if maybe he really did have a cunt. If Lily could have a cock why couldn't Cadence have a cunt? But I then remembered his dick laying in my palm earlier.

I ad libbed, "Oh Cadence I've wanted you for just as long. I need to lick your pussy and nibble on your clit." With some hesitation, I pushed the black mini skirt up above the red panties exposing his large dark dong sticking through the crotch of the panties.

Calla got behind me. Reaching up under my skirt she pulled my own balls and penis through my crotchless panty. She manipulated them gently with her hands, bringing me to full hardness.

Cadence continued, "Start with my labia. Lick em good before you suck my lady part. I'll give you an extra twenty if you do a good job."

Lifting his cock out of the way I bent down, applying the tip of my reticent tongue to his grotesque balls, figuring that they were the closest deformed equivalent to labia that a guy would have. I didn't really love having my tongue on a man's hideous wrinkly nutbag but Cadence loved what I did.

Bent down low, my backside was raised high. Calla kept playing around with my own sensitive balls and cock. Caressing them and tugging gently she pulled them this way and that, it slowly dawned on me that, after cutting off the panties, she was fitting them into some kind of unseen contraption.

A cold metal ring clamped around my balls just above my testes. I accepted all she did as it was the only way to be released from my debt. Of course, Rose would never allow them to damage me. Trapped by the ring my jewels were pushed down further than they normally hang.

I was still attending to Cadence's wanting orbs.

When Rod topped me I hadn't licked his balls, and I never even saw the kid's balls from earlier tonight. These were the first balls to ever touch my tongue. Knowing he wanted me to do a good job I applied myself with inner turmoil but outer fanaticism.

Rod had forced himself upon me, alleviating me from responsibility, but Cadence and I traded freely in commerce. I was a willing participant here. He being more willing than I.

Letting saliva flow liberally, I bathed his scrotum, swirling my tongue over the whole potent sack and feeling the needy testicles jostle within. I imagined those testicles pumping out cum causing his balls to expand like a balloon as they stored greater and greater quantities of sperm yearning for release. Given how big his glistening ballsack was, it must contain a copious payload.

Precum was practically streaming from my penis, perhaps being milked out of my balls by the tight band? I felt the band adjust as she angled the apparatus. She proceeded to insert a cold metal ball into my rectum, squealing, "This is my favorite toy. Sticking it up your ass really gets my blood going!" Her comment gave me a feeling of contentment.

Cadence piped up, "Did you use the one with reins, Daddy?"

Calla responded elated, "I sure did, Cady. I thought you would like that one. How about you Chucky?"

I stopped slathering his balls long enough to lift my head. I hadn't known that they were going to use toys on me. I didn't even know there were toys for one's anus. Hearing them get so excited about the toy gave me a newfound interest in it. I wasn't ready to express unreserved enthusiasm but I did offer that it felt 'kinda' good.

Returning to his spit soaked balls, first I kissed them, thinking that would show adoration, then tried giving them a suck. He moaned appreciatively.

With each forward entry of the metal ball I felt a matching backward movement of the band grasping my balls, allowing me to deduce that the rod and the band were two parts of the same toy.

As it went up my ass I understood that the ball was the tip of a metal rod which in turn was connected to the metal band. It curved down from my asshole to my nuts. I pictured a giant blunt hook.

Meanwhile, the proof that my licking was good became evident as his appreciative black cock soon towered above me.

Calla passed a couple strings to Cadence. I supposed these were the reins. Seeing his happy cock I determined to become totally dedicated to it. I would do whatever it took to make Calla and Cadence overwhelmingly ecstatic.

I had a girlfriend once who used to nibble up my dick from base to tip, biting gently as she went. I adapted the technique when I would nibble on my wife's pussy lips. However, now I decided I could do it exactly as that long gone girlfriend had, but applied to Cadence's cock.

Starting at the juncture where balls joined cock, I opened up and, using my teeth, gently grasped his rigid cock. Cadence moaned extra loud prompting Calla to peek to see what was happening.

Seeing me biting the side of his pole she exclaimed, "Wow, he's biting you? Does it hurt good?"

Cady answered her calmly, "No. it actually feels great."

Either she couldn't believe it or she didn't want to, "I wasn't planning on it, but since he's into it, let's give him a little pain." I figured she would spank me.

I continued biting up to the top, then looked Cadence in his leering eyes, "Did I earn the extra twenty?" Remembering that they loved the prostitute theme I guessed what a prostitute would say next. For good measure I tried to make my voice sound female, "For another twenty I'll do a good job on your cock too."

Calla was fiddling around back there with my balls planning who knows what.

Cady affected the prostitute role, "Sugar, you earned that first twenty fair and square. Here's a little extra for what's coming." Saying that he handed me two yellow hundred dollar bills."

I took the Monopoly money and promptly turned to hand them over to Calla, "Here you go Daddy." I saw she was holding some small wooden objects but didn't have the time to figure out what they were before Cadence pulled on the reins returning my attention to his cock.

When he pulled on the reins it yanked on the metal rod with the ball on the end and also yanked on my balls. It could have easily hurt if he had pulled harder.

He grabbed my head with both hands bringing me lips to his cockhead. He was holding tight so I couldn't bob. All I could do was stay still while he placed just the head of his cock in my mouth, "Now suck like a good girl, but no biting. No matter what happens back there."

His forceful grasp on my head and the ominous warning rattled me a bit. Just then there was a sharp pinch on my balls. I winced but made him proud by not biting. Whatever she was doing was painful but not excruciating. After the initial shock it was even quite bearable. If it made her happy..."

The first pinch was followed in rapid succession by, like, fifteen more. Cadence felt me jerk a little with each one, "Hey Daddy, how's it going with the pins?"

My mind exploded, 'pins!' Could she really be sticking pins in me? It didn't feel like pins.

Talking to Cadence she said, "He looks amazing! Like a porcupine with all the clothespins clipped to his nuts." That was a relief.

I was totally focused on the thousand volts of sensations between my legs: the ball and rod up my ass shifted with any provocation, the tight ring on my sack shifted them forwards and backwards frequently, the mass of clothespins pinched the thin skin of my scrote continuously, and her constantly unexpected manipulations were always changing. I was barely aware that there was a cock in my mouth. Who knew that pain could register as pleasure?

My cocksman noticed how distracted I was. He pulled on the reins to get my attention. Did it ever! Those thousand volts turned into a million.

As I sucked feverishly he guided my head up and down groaning as the long shaft worked its way deeper.

I heard the snap of latex gloves and reckoned that she was going to put something new in my ass. I felt my hard cock being gripped and pulled back by a latex-covered hand. But she didn't put anything up my butt.

Cady was trying to insert his fleshy shaft into my throat. It kept hitting but not going in. I was gagging every time, resisting the urge to upchuck, 'cause I didn't want to spoil it for him.

My mind reeled when Calla tried to insert a tiny cold metal shaft into the end of my dick. Fireworks went off in my brain! The million volts in my groin turned into two million. It pushed me over the edge.

When my balls contracted my ass squeezed on the stick up my ass, the metal ball pushed my prostate, my nuts retracted and every clothespin on them pinched simultaneously, then multiple globs of cum surged through my urethra. It was the strongest orgasm of my life.

My body convulsed, my hips thrust forward involuntarily, my stomach tightened and I gulped in surprise. Cady discovered that moment when my throat was receptive and jammed a couple inches in there.

Now that I'd cum Calla gave up on sticking the metal rod in my dick, and grew tired of misusing my testicles, so she came up to watch the mistreatment of my throat. The first thing she did was to wipe my cum from her hand into Cadence's shaft. The second thing she did was to straddle my back pushing on my neck with both hands.

MVP6
MVP6
701 Followers
12