Risky Business

I think everyone is probably familiar with an early Tom Cruise movie called Risky Business. The plot involved an entrepreneurial young man looking for a way to make extra money while trying to decide whether or not to attend college after graduating from high school. In essence, he became a pimp by recruiting young ladies to take care of his buddies, classmates and friends at his parties. Of course, his friends would pay him handsomely to bang these young hookers. A brilliant concept and a very edgy movie in its day.

After I graduated from college, I had an experience that inspired me to use the model from Risky Business and take it to whole new level involving milf moms, mature wives, and their adult age daughters.

It all started when I attended a company sponsored Halloween party where entire families were invited. A lot of the wealthy executives, Including my boss, Bob were there with their trophy wives, and their trophy daughters. There were also many single moms as well accompanied by their adult daughters looking for a good opportunity for networking, and to also have a good time. There was a lot of pussy in that room, and I fully intended to get some that night

Everyone seemed to be hitting on each other's wives, husbands, and daughters. Bob's wife and teenage daughter were paying a lot of attention to me flirting with me all night long making very suggestive comments while trying to get me to sneak away and join them in one of the private offices. I was tempted, but also worried about getting caught so I declined.

Both mother and daughter were dressed in sexy witch costumes, which has always been a total turn on for me. The mother, named AJ, was wearing a classic Elvira costume slit open to her upper thigh with a deep, plunging neckline, open down to her belly with no bra. Her costume barely covered her large, free swinging milf tits jiggling with every step she took. She had the classic Elvira black wig and was also wearing black lipstick. Little did I know that I would get to watch Elvira suck me dry with those mature black lipstick covered botox lips later in the evening.

The 19-year-old daughter Holly was dressed like the Samantha Stevens character in the TV show Bewitched. Holly was well endowed just like her mother and showed off her teenage tits with a plunging neckline and a push-up bra. Her Bewitched costume was split up to mid thigh just like her mom's. Holly's young pouty lips were thoroughly covered with bright red lipstick. Once again, little did I know that later that evening Holly would be leaving a red lipstick ring not only on my balls, but also on my stomach at the base of my cock after deep throating me.

As the party was winding down everyone was getting pretty wasted, including the mother and daughter witches and Bob. None of them were in any condition to drive, so I offered to get them home and they could pick up their car the next day. I was glad they excepted my offer, giving me more time to try to take advantage of the mother and daughter witches.

We struggled to get Bob into the backseat of the car, giving me a nice look at one of AJ's magnificent braless tits as it slipped out of her dress? Young Holly joined me in the front seat teasing me by crossing her legs giving me a nice look at her firm, meaty thighs with her costume dress almost slit up to her pussy.

Once we got to their home we again struggled getting Bob into the house since he was sloppy drunk, and falling asleep. We eventually dragged him into the guest room, put them on the sofa, covered him up with a blanket. He was definitely done for the evening. Now it was my opportunity to see if I could get some witchy pussy.

I did not have work very hard since mother, AJ and daughter Holly were drunk and ready for some action. AJ asked me,

"James, how can we make it up to you for going out of your way to drive us home tonight?"

Holly jumped in, "Dad's out cold so it's only the three of us."

With that both AJ and Holly approached me, putting their arms on my shoulders, and alternated between deep kissing me and kissing and licking my neck going all out to seduce me. It was even more erotic with Bob laying no more than 10 feet away out cold on the sofa. I was not only going to live my fantasy of fucking a mother daughter combo, I was going to do it right in front of AJ's husband, Holly's dad and my boss. What a total turn on.

AJ and Holly were not going to let me leave their house without getting some cock. They had been wanting cock all night long and now it was their time to pay me back. I quietly told both of them.,

"Show me your tits witches, and get on your knees."

AJ slid her Elvira costume off her shoulders and let it fall on the floor, revealing some magnificent 48 year old, mature, big nippled tits. Holly did the same, removing her bra, showing off her 19-year-old, puffy nipple teen tits. Both women were now only wearing thongs that match their costumes and high heels. It was now time to suck some cock.

They pulled off my Spider-Man costume pants and went to work on my hanging balls in my rock hard cock. They were licking both sides of my cock, occasionally stopping to deep kiss each other before returning back to my manhood. Bob was still fast asleep as his wife and his daughter we're giving me the best dual blow job I ever had.

AJ had me lay on my back on the floor as they both stood over me and removed their panties. AJ had a nice full bush and young Holly had a nice landing strip. AJ immediately sat down cowboy style on my cock while Holly sat down over my face. I was licking out Hollys tight, sweet pussy while AJ agressively bounced on my cock, wanting to feel a toe curling orgasm.

The women embraced and started kissing each other as they continued to grind their pussies on my face and my cock. It did not take long for both of them to have moaning orgasms with Bob fast asleep on the couch.

Before I left, I made a point to get a screenshot of Bob's wife and daughter sucking my cock and balls leaving a ring of Holly's red lipstick on my cock and a ring of AJ's black lipstick on my balls. I told them I also wanted their panties as a souvenir and they agreed.

I tormented Bob for years by anomousily sending him a photo of my full erection with his daughter's red lipstick ring around my cock and his wife's black lipstick ring on my balls with both pairs of their panties, hanging off the end of my cock. He never figured out And had no idea he was looking at my cock, his wife and daughters panties and their lipstick rings, circling my dick. Likewise, I blackmailed AJ and Holly for years for unlimited sex, threatening to show Bob the photo.

That night was the start of a brilliant business concept. I am sure just about every adult male has fantasised about fucking a milf mom and her daughter, and I was no exception. Threesomes have always been a passion of mine, but it takes it to the next level when it involves a mother, a wife and her daughter.

I started looking into advertisements for escort services, and to my amazement I did not see any ads offering to fulfill the mother daughter sexual fantasy. That is when my business concept was born.

I started running my own ads in similar publications to see what kind of interest level I would attract. I was overwhelmed by the number of hits by men of all ages willing to pay over $2000 an hour for a mother daughter sexual experience. I immediately went to work recruiting, milf moms and their adult age daughters to fill the demand with the promise of big money for their services.

I actually found it quite easy to attract women that wanted to make extra money and also enjoyed sex. All of my contacts were established online. I ran ads on various websites attracting many hot milf moms and their daughters or stepdaughters.

The women would send me screenshots, or detailed descriptions of themselves and what they were willing to do ie gangbangs, anal, bondage, spanking etc.

I set up a catalog online for male customers to choose which mother and daughter they wanted to fullfil their fantasy. Once the selection was made, I would set it up the rendezvous, and the money would be sent to me electronically for me to re-distribute to the women. The women also needed to agree that they would make themselves available for me to fuck anytime I wanted.

Business was good, and I was making money hand over fist for a couple years. That is when I but I got the shock of my life. One evening I received an inquiry from a mother and daughter that Wanted to be added to my list of mother and daughter sex duos.. Photos were not provided, but Instead a very detailed description was provided. The description of the milf mom and daughter sounded very much like my own trophy wife in my 18 year old high school cheerleader step daughter.

I would be lying if I didn't say, I had mixed feelings about pimping out my own wife and my step daughter but the eroticism of the idea totally turned me on. I needed to find out so I immediately booked a rendezvous for them with one of my best customers. This guy would easily spend $10,000 a month to unleash his sexual fury on milf moms and their daughters.

One of the stipulations to use my service was that customers were not allowed to take cell phone screenshots or videos of my women to maintain anonymity. In reality, I'm sure most of my customers took videos because I would've done the same thing, but I had to establish some type of guidelines.

On this particular occasion, I made an exception for my customer to discreetly FaceTime me of the entire experience. I felt erotically dirty over what I was about to do, but I was also totally turned on by the idea.

On the night of the appointment, both my wife Dorthy and stepdaughter Allie told me they were going out with some friends for girls night out. They were both dressed like a couple of sluts wearing short skirts, high heels and low-cut top showing a lot of cleavage. I acted totally uninterested and told them to have a good time.

At that point I was feeling pretty confident that I was going to be watching my wife and stepdaughter get fucked hard but I had no idea how bad it was going to be. I was anxiously watching on FaceTime and I was about to find out. My suspicions were soon confirmed.

My 50 year old, redheaded, big tit milf trophy wife and my 18-year-old red hot high school cheerleader stepdaughter appeared to be very comfortable entering the hotel suite and were greeted by my customer.

Unknown to me this particular customer was a 40 year old black man with a shaved head and the physique of a bodybuilder. He also had a passion for fucking white women. He always requested white milf moms in their 50s and the daughters as young as he could get. My wife and step daughter fit the profile perfectly. I knew this might be the roughest hour of their lives.

My customer was in amazing shape and appeared to have an impressive package strainng against his pants. I was about to watch my wife and stepdaughter get pounded by their first black cock, and I was hard as a rock with anticipation.

He started by pulling both of them towards him and alternating kissing my wife and my stepdaughter. I could tell both of my women were getting turned on as he reached down and grabbed both their asses with his massive hands as he rolled his tongue around in their mouths. He poured himself a drink and took a seat.

He started out with my wife Dorthy by putting on some slow, jazz and saying,

"Mama, why don't you start out by slowly stripping for me. I want to see what I'm paying for. He then turned to my stepdaughter Allie, and told her,

"Come over here and sit on my lap princess, I want you to feel what you're going to be enjoying for the next hour.

Dorthy was seductively swaying to the music as she reached behind her back and pulled the zipper down on her dress she letting it slide off her shoulders and fall to the floor. She was wearing a very sexy and slutty, matching bra and thong that I had never seen before. She reached behind her back, unclasping her bra also letting it fall to the floor, exposing her magnificent, big nipple tits that I was very familiar with.

He told her to leave her panties on and to keep dancing. He wanted her to watch him take advantage of her 18 year-old cheerleader daughter right in front of her face and knowing that I was also watching. He knew damn well he was gonna be violating this young lady in front of her mother and her stepfather, and he was totally turned on about the idea.

As Dorothy continued swaying to the music, my customer started to run his hands up Allie's skirt, enjoying the feel of her soft teenage inner thighs. He Unbuttoned her blouse, pulled it aside, exposing beautiful 18-year-old tits being held by a very sexy push up bra.

I could tell by Allie's expression that she could obviously feel his cock growing as she sat on his lap. He pulled up her skirt so she could feel his cock pushing up against her thong covered ass. He could no longer resist playing with Allie's tits. He unclasped her bra and threw it on the floor.

Both he and I are now seeing my stepdaughter's teen tits for the first time and they were magnificent. Unlike my wife's large hanging milkers, Allie's young tits, were firm as a rock. poking straight out with classic 18-year-old teenage puffy nipples.

My customer motioned Dorothy to come over so he could play with both their tits at the same time. He was enjoying the contrast of Dorothy's hanging milkers and Allie's teenage pokers that could put an eye out.

He enjoyed looking them straight in the eye and watching their reactions as he pinched one of each of their nipples pulling them straight towards him. He let out an evil laugh as both my girls started to whimper. It was now time for my wife and daughter to see the most amazing cock they had ever seen.

He told Dorothy and Allie to get on their knees unzip his pants. Both women eagerly followed his commands. He lwas going commando, and both girls were immediately stunned as his BBC sprung out of his pants and hung right in front of their faces. Quite honestly, I was even shocked at his size and he wasn't even hard yet. Took off his pants and shirt said and let my wife and stepdaughter go to work on his cock and hanging balls easily getting him hard within minutes.

"Get to work girls, I only have 30 more minutes to get my moneys worth."

Dorothy and Allie simultaneously started licking his shaft from his tip to his hairless shaved balls. I am sure they were becoming aroused, yet somewhat fearful, as he started to grow to full size. I knew Dorothy could handle his big black monster, but I was not so sure about Allie. Once he was grow to full size, he walked my wife and stepdaughter over to the bed and laid them on their backs with their legs hanging over the edge of the bed.

He lifted both ladies asses off the bed and removed their panties and started licking their pussies, alternating between Dorothy and Allie. Both women were overwhelmed with his pussy eating expertise with their heads, raising and slamming off the mattress in lust bringing both girls to a twitching orgasm.

He started his black cock punishment with my wife by grabbing her ankles and pushing her high-heeled legs back behind her head with his cock head rubbing against her pussy lips with no hand to get her ready. Her eyes widened as he started to work the head of his cock into her mature, red haired pussy. Dorothy was taking it well. She locked her ankles behind his back and let him use her pussy as a good slut should.

After pumping Dorothy to another full orgasm, he shifted his attention to Allie. He did the same routine with Allie by grabbing her ankles, putting them behind her ears, and rubbing his cock head over her young shaved pussy. It became very obvious by Allie's, screaming and moaning, that she was not going to be able to handle his cock. But she could sure handle his tongue. He laid on his back telling Dorothy to sit on his cock cowgirl style, and for Allie to steaddle his face while facing her mom.

For the rest of the hour, my wife pounded his black cock with her pussy bringing herself to multiple orgasms. Allie was in heaven, having her pussy eaten out with skill also having multiple climaxes.

My customer could no longer contain his busting balls and needed to unload. He told both women to get on their knees, and he cranked a thick load spraying both their faces with creamy thick jizz.

After he had thoroughly drained his balls, my wife and stepdaughter clean themselves up, got dressed and headed home.

When they arrived home, I acted like it was just a normal night, however, it has been anything but normal. I had of course, recorded the entire event that I would enjoy watching and jacking off to for years even sharing it with some of my buddies..

I did, however, make a point of making Dorothy have sex with me that night. I wanted to see what her pussy felt and looked like having been jackhammered by a massive black cock. Her pussy had been stretched, and definitely felt different, which was a total turn on. I made a point to eat her out to get a good look at her her red swollen pussy lips eventually dumping my load balls deep in her tired pussy.

It was a win-win situation for me that night. I made money from my customer and so did my wife and step daughter keeping it in the family. I fully expected to receive a message the next day from my wife and step daughter requesting that I remove them from my list as escorts because of the beating they had taken that night. To my surprise they wanted to just the opposite. They requested as much action as I could send their way.

Successful businesses need to take some risk to be successful and my business for sure was Risky Business.