A Naughty Night Out with My Sis

I was having a great Thanksgiving with family and my sister Angelina who we call Angie, until she dropped a bombshell. She and Jerry were going through a nasty divorce. I did wonder why he didn't drive out with her. She gave us the details of his deceit for a year the rest of the night.

I've always like Jerry and have a hard time wondering why he would cheat on her, after 9 years of marriage. I think she still is attractive even after having two wonderful kids. She's 5'6", long sandy hair, slender, blue eyes and B cup boobs. In case you haven't read my other stories, I'm 5'5" red hair, blue eyes, nice slim figure with 34D boobs. I've been told that I have a cute ass. But knowing guys like I now do, men will do anything for a cute piece of ass. I guess Jerry was no exception. The girl he is seeing now is only 22, has long blonde hair and according to Angie loves to suck cock. With an ugly expression she said that had always disgusted her. Angie cried when she continued elaborating on the situation. So I changed the subject.

I suggested going out Saturday for drinks and dancing to cheer her up. I also needed more information and maybe after a few drinks, she would loosen up and tell me the real reasons. Our mom said she would watch the kids who are 5 and 7. Being with Jerry since high school and never seemed to party much, I was somewhat surprised that she agreed without a lot of persuasion; although she wanted to be back by midnight because of the long drive back to Phoenix the next day.

So Friday we went shopping for the perfect clubbing outfit. She fell in love with this two piece short black flowered skirt and a black matching top with 5 buttons down the middle. I have to admit, my 5 years younger little sis, look very alluring in the conservative outfit. Mine outfit was a red two piece with white polka-dots. The wrap around skirt went down to my knees, with a slit in the middle and held together by one clasp. The top was also a wraparound that tied in the middle and nothing else holding it together. We looked very hot together, at least that is what I thought when we stood side by side looking in the mirror. Saturday we went for pampering by getting our hair done and manicures. We were looked very glamorous when left around 6 pm for dinner.

At dinner Angie told me the rest of the story that she cheated on him first with a guy she met at the gym. She said it was a mistake, but she was bored with being just a house wife and needed some excitement. Then she laughed and told me that the sex was fantastic. But now he's gone too and she hasn't had sex in over 3 months. Then she gave me another surprise. She asked how having sex for money made me feel.

Oh my god! My secret is out. I thought no one in the family knew. I guess it was now my turn to fess up.

"Well Angie," I started. "The first time was scary. I started as a fluke during a date at a hotel one Friday night. Then a couple of guys dared me to come back and continue escorting the rest of the weekend. So I challenged them to get me three dates for $500 a date and I would. I didn't think they could, but they did. So I went back and had a great time making guys happy. That was over three years ago. But Angie, all my dates aren't fun. Some you just have to get through them and relish the exciting ones. It's not for everyone and I sometimes regret my decision and feel ashamed. But by the next date it passes quickly." I laughed after I said that. "I do love what I do; and making guys horny by seeing me, is a fantastic feeling."

"Oh I see," she answered. "Jerry called me a whore just like my sister, when he found out about my cheating. That's when I found out about you. He showed me sites with your explicit photos were posted advertising a GFE). Whatever that is! I didn't know what to think. But then I started wondering what it would be like not answering to any guy and just enjoying the sex without any commitment."

Oh my god! I thought I had deleted the photos from those sites. Since working exclusively for the private sex club, I have no need to continue advertising. I now wonder who else in the family has seen them. Angie quickly eased my mind.

"So Kat," she said. "No one else knows but me. I only told you because I want you to teach me. I've always pondered what it would be like to have sex for money. After my cheating, I found out that I love sex and realized I wasn't getting enough with Jerry. It was always in missionary. I want to experience more men, more positions and more orgasms. Jerry hasn't giving one of those in years." Then she laughed and said, "I also need the money. The 4 hour a day waitress job I took while the kids are in school, won't pay the bills. So can you help me? It will be our little secret just like when we smoked pot and we didn't tell mom and dad."

Oh my god! My little sis wants to try being a working girl just like me. I guess I can understand her need for sexual experiences. I was the same way after my divorce and I had sex with more guys before marriage than she did. Jerry was her first. And at 28, I guess she has a lot of catching up to do. I know I did.

Looking into Angie's eyes I asked, "Do you want to start tonight." Her eyes instantly turned to excitement and smiling she nodded yes.

The rest of dinner she kept asking me questions about my past sex dates, how to ask for money, and how much. Then she saw two guys sitting at a table looking at us. They were cute and she told me that she liked the clean shaving one. I told her we should go to a bar instead. If they were interested in us, they would follow, but we shouldn't be easy to be picked up. Angie laughed, paid our bill, and we left.

It was still before 8 pm as we slowly walked down the crowded street to a club. There was no line when we went in and found two seats at the bar. While we were waiting for the bartender to finish flirting with a couple of girls, we heard in some sort of a European accent, "Can we buy you ladies a drink?"

The guy that now took the seat next to me was from the restaurant. He was cute, with dark wavy shoulder length hair, a trim black beard and these brown eyes that look straight through you. He said his name was Josh. Angie had the other guy that she liked next to her. He wasn't as tall and had short hair. His name was Chet. They then bought a pitcher of Margaritas and talked for a while. I acted friendly by touching his arm and leg a few times and laughing at his stupid jokes. With my legs crossed he touched my knee and then told me that I was very beautiful. Once the pitcher was finished, they coaxed us to move to a booth in the back. We did with me and Angie sitting in the middle and the guys on the outside of us. Another pitcher of Margaritas was ordered, which we drank most of, while getting friendlier with the guys. Eventually, Josh and I were kissing with his hand up my skirt rubbing my pussy over the panty. I didn't stop him until he moved the thong to the side to rub my bare clit.

"Oh Josh, you make me very hot," I whispered. "But I need to go pee. I'll be right back."

Turning to Angie who was lip locked with Chet I whispered, "I need to go to the rest room. Come with me."

She stopped kissing Chet and I saw him remove his hand from under her short skirt. The guys moved aside and we left for the rest room. I turned and looked back and the guys were intently watching us walk away. Once we went in the restroom, Angie blurted.

"Oh my god Kathryn, Chet really wants me! Now do I ask for money?"

"Leave that to me," I answered. "But let's make them so horny that they can't say no."

I removed my bra but Angie; still somewhat modest, kept the bra on and only undid the top two buttons so they could get a good look at her boobs. With mine off I loosened the top a little. My breasts and nipples were nicely visible from under the silk material. Angie's wasn't. After discussing a game plan, we went back to the boys. They moved aside and we slipped in the middle again. Josh's eyes instantly went to my breast. I'm sure Chet's eyes did the same to Angie's boobs. I passionately kissed Josh as Angie did the same with Chet. When we broke for air there were 8 shots of Tequila in front of us. The guys gave us each a shot glass and we toasted to our new friendship. After we drank the yummy booze, Josh looked deep into my twinkling eyes, took a hand and pulled my top apart exposing more of my breast.

"You have fantastic looking tits," Josh whispered.

I giggled and as I heard Chet blurt that Angie's breasts were nice too. Looking over I saw that Angie's top had four buttons now undone with her bra pulled off her breast. I guess he undid the clip in the back.

Then Chet asked, "Why don't you girls come back to our hotel with us. I guarantee it will be a most memorable night."

Angie giggled as she put her hand on Chet's leg and answered, "Would love to for a fee."

I expected them to be shocked, but instead Josh put his hand under my skirt rubbed my pussy and whispered, "I thought you two were working girls when we first saw you. We have talked about how much you girls were going to charge us. To make it easy we'll give each of you $500 if you fuck until we are done with you."

That comment gave me pause, but before I could answer no, Angie replied, "Yes, we love too."

Chet answered, "Great! We'll all going to have so much fun, but especially you girls. One more toast to a night of illicit behavior."

Then Josh laughed and added, "You mean until the sun comes up." We all had a nice chuckle from that comment.

Taking the shots, we clicked glasses and guzzled it down. It did taste a different then the first shot, but I didn't think anything of it. Then Chet took out his phone and took a photo of each of us with our breast partially exposed. He fiddled with his phone and I heard ding getting a text back. Smiling, he told Josh that Uber was on its way.

Once outside we walked down to a bus transit pick up that was deserted. Sitting on a bus bench by the curb, we waited for an Uber pickup. We continued kissing as they groped us. They even took a few photos of us. First it was Angie with her breast exposed and her legs spread wide apart. Chet told her that she was really hot in posing and asked if she ever modeled. She giggled and told him no. They took off her panty and she pulled up her skirt for a few more poses. Then it was my turn on the bench, while Josh took a few photos in the same poses. They told us it was for remembering this night being with two gorgeous women, but they fiddle with their phones for a few minutes afterwards. After a short time of more kissing and groping, a big white transit van pulled up. Chet opened the side door. I thought it was strange that there were no seats or windows. Just big cushy pillows scattered around the inside with carpet on the floor and a string of red Christmas lights strung around the top. The driver looked Middle Eastern as he told us to get comfortable.

Angie was by the back door leaning against the side wall with Chet kneeling next to her. I was on the opposite side of the van closer to the front with Josh in the middle of the van next to me. It seemed that they put us as far from each other as they could. As I sat up, Josh came over to me and pulled my top apart showing him my full breasts. He stared at them for a minute.

"Those are some nice tits you have Kathryn," he said as he began kneading my nipples. "I love making a girl's nips nice and erect. You like them being played with too, don't you gorgeous!"

All of a sudden I was becoming very horny. My pussy was getting hot. This was a something I felt at the sex parties after they squirt some mint flavored spray in my mouth. But nothing was given to me, so why was I becoming so freaking horny? Although, that last tequila shot did taste a little minty.

Becoming very submissive I sensually answered, "Oh yes! I love my breast being loved. Oh god that feels so good. You can do anything you want to me."

He laughed, took out his phone and told me to smile as he took some photos of me. Afterwards, he moved down to my skirt. I had my knees tightly together as he opened the wrap around slit to expose my pussy. Finding the clasp that held the skirt together, he undid it allowing the skirt to fall off me. All I now had on were my white stockings, garter belt, shoes, and top. Josh told me to open my legs and he began shooting more photos of me. As he did, I looked over at Angie. She was on all fours with Chet's hand in her pussy. Then I saw him move back and took photos of her. A few minutes later I was on all fours with Josh taking photos of me in the same positions.

When he was done with that task, I was back sitting up against the wall. Josh put his hand on my pussy again and began fingering it. "You have a very nice shaved cunt Kathryn, and it's very hot and wet. I bet you can't wait to feel a big throbbing cock inside you right now. You want it don't you?"

I was moaning in pleasure as put two fingers inside me. "Oh god that feels so good," I blurted. "Yes I do want to feel you in. Oh yes I do!"

"I know you do gorgeous," he laughed. "We'll almost at the hotel. It won't be long until you'll get all of the cock you are now craving. Your cunt has primed up nicely." He laughed.

I looked over at Angie and she was moaning in pure ecstasy as Chet played with her pussy. As Josh continued fingering me, I was also moving my hips in pleasure wishing it was a cock in me. He looked at me watching Angie and snickered.

"Don't worry," he whispered. "Your sister will be having just as much fun. I put a little incentive in that last shot you girls drank. It seems you two have responded very favorable to it. You'll be begging to get fucked in a few minutes." He laughed again.

When we finally got to their hotel, it was a seedy looking place with a red neon sign saying hotel and no vacancies lit under it. Angie didn't even notice it because she was kissing Chet. I notice that all of the buttons on her blouse were undone, no bra with her boobs hanging out and her skirt pulled up making it a micro mini skirt. I wanted to put my skirt back on, but Josh grabbed it and exited the van. He moved to the side of the door and took my hand. As I slithered out, I was bare from the waist down expect my stockings and shoes. Once out of the van, I pulled down my top as far as it would go and it only covered the top half of my ass with just enough material to hide my dripping wet pussy. His arm was around my waist, as he walked me inside the sleazy establishment. Angie and Chet followed with her blouse being pulled off her breast for anyone to see.

Once inside, a large Hispanic guy with a few tattoos on his arms was sitting behind the counter. There were 5 or 6 guys sitting in the small lobby room off to the left. Some were looking at their phones others at a TV, which I couldn't see what was on it. I heard one guy say to the other about when the new whores were going to show. His friend told him to look in the lobby. They stared at us with lusty leers that Angie was still oblivious to what was happening. She was giggling as we stop at the desk.

"We finally made it Diaz," Chet said. "I have these two hotties to check in. They are more than ready to service everyone. I hope they meet with your approval."

Diaz leaned over and looked at us and didn't even smile. With a scowl he asked, "You Ladies know why you are here?" After he said that, Josh and Chet snickered.

Giggling, Angie didn't even hesitate and answered, "Yes we do. And we're looking forward to it."

"Oh my god Angie," I shouted. She looked at me in confusion.

Before I could say anything else, Josh slapped my bare ass and whispered, "Behave Kathryn. You're already here. Even if you don't want to fuck in your head, your cunt does."

Diaz told Angie to look into his phone and say her full name, where she lives, and if she was here willing. She answered as they wanted her too. She then signed the register and he told her that she had room 6.

When I got to the counter, I looked over it at a series of monitors. They were all facing away except one which had a black girl on all fours having sex. I guess Diaz noticed me looking and said something about how he's going to enjoy watching me getting hammered. I answered the questions the same as Angie, signed the register, and was assigned room 7. Then Diaz took our purses and told us we would get them back filled with our earnings when we leave. I knew what the place really was and how the van really wasn't an Uber but just a pick up car. I thought at least we'll make some money from this lesson.

As we approached the stairs, some guys followed. I heard one guy say that he really like the red head and her bare cunt. As we went up, I looked back to some guys looking at us walking up the stairs. Then I heard a guy saying something about seeing our bare pussies. Another say he liked the blonde while others made nasty comments and asking when we would be ready.

Josh stopped and answered, "Give me 10 or 15 for them to get settled before you guys start having fun. I know they will give you guys a great time. And for you anal lovers, they both are full service for an extra fee."

By now I was really horny to feel some cock in me. Just like Josh said I would be and like when at one of the sex parties I attend. Angie was ahead of me and stopped at the top.

Trembling as she turned to me, she inquired, "Kat, is this really happening? Are those guys down there going to have sex with us? For some reason I'm really horny wanting them too and I've never felt this excited before. Do you feel the same way or is it just me?"

I replied, "I'm so freaking horny too sis. But yes you're going to get your wish. You will be having sex for money with a lot of guys."

Then Chet added his two cents, "Don't worry Angie. When you're done fucking all of these guys tonight, you'll no longer be a lady, but be one sweet worn out whore." He laughed afterwards, which made Angie stop walking until he dragged her ahead.

As we continued our struggle down the long hall, they stopped, opened room 6 door, took Angie's hand and pulled her in. I stopped to watch her whining, "But I've never done anything like this before and only had 2 other sexual partners. I'm a good moral girl and don't want to become a trollop!"

Chet gave out aloud hoot and replied, "Only 2 guys! You'll probably quadruple that number tonight! And gorgeous, after you've been begging for sex while servicing our clientele for hours, you wouldn't care what we call you." He laughed.

Chet slammed the door and I was yanked to the next room. At least it was right next to Angie's. The pungent aroma of sex filled the small room. It had a double bed in the middle with mirrors on two walls and the ceiling. There was a sink and toilet in the corner. The only lights in the room were a string of mixed red and white Christmas lights hung high on the walls all the way around the room. Once inside this dreary smelly sex den, he told me to take off my top but leave my stockings, garter belt and shoes on.

He laughed and said, "Cutie guys like seeing a little clothing on a girl when they fuck them."

Afterwards, I sat impatiently on the side of the bed with my legs hanging over the edge. Josh came to sit next to me. He kissed me again and began rubbing my pussy. I was already nice and juicy and wanted him real bad. But instead he started talking to me, as he gently fingered my clit.

"Well Kathryn, you are the best looking girl I ever brought here. I'll be getting a big bonus for bringing you in. I know you'll have a good time by how wet your twat is. There is a box of condoms over there and a bottle of lube for your ass. If you run out of either, just ask for some more by yelling what you need. They have mics all over the place so they'll hear you. Don't worry either. As a working girl, they will pay you for your services that is, if you fuck the guys without any problem. I got to go. Have fun sexy."