I was working at a brokerage house as their IT man. I was very young for my age being eighteen. I had worked there since I was sixteen and bought a foreclosed penthouse from the IRS with the help of a friendly broker. It had four bedrooms, five bathrooms and a spa on the wide balcony.
My parents had helped me move and even my fifteen year old sister Virginia had helped. Of course I bought cheap furniture and accepted the king sized bedroom set my parents gave me. Dad’s sister, aunt Meg was only twenty two and a roll model for Virginia. She had worked as a waitress for the last year.
It was the start of summer and I came home very early to find my sister and aunt Meg waiting in the small entrance outside my door. I smiled as I let them in and set my laptop down on the hall table, “visiting to use the spa?”
Meg grinned and took my hand to pull me after her and into the living room, “we need a favor.”
She surprised and shocked me when she turned after leading me out the balcony door. She began stripping me and I glanced at Virginia to see her undressing. I stared at my sister’s naked body and she grabbed my hand to pull me to the spa as Meg undressed. I climbed in and Virginia surprised me again by sitting on my lap.
I knew she felt my hard cock but she didn’t say anything. Meg slipped into the hot water and moved to sit beside me, “we need a favor Tom. I’m not really making any money... we were going to start selling our ass and your place is nice...”
I looked at her and then at Virginia, “you’re fifteen.”
She wiggled, “I’m old enough to take a big cock like yours in me.”
I looked at Meg before moving my sister off me and climbing out. The thought of what they were going to do had my cock drooling. I went to my pants before coming back with my cell. I slipped into the warm water and moved back between Virginia and Meg. I took a breath and looked at Virginia, “have you had sex yet?”
She looked at Meg and shook her head. I leaned back and set my phone on the edge before reaching for her. I pulled her onto my lap, straddling me and positioned my cock before pulling her down. I forced my cock into her slowly and she wiggled to help. Once I was all the way in her and against her, I sighed and turned to reach for my phone.
I looked at Meg and hugged Virginia, “you use condoms.”
They nodded and I looked back and forth, “I will managed the money and pay you.”
They looked at each other before nodding again. Virginia’s tight pussy squeezed my cock as she shuddered and started to rock slowly. I turned to the phone and called one of the main managers, “Mr Phillips?”
I smiled, “still looking for entertainment for those clients?”
I looked at Meg, “I know two whores that would love to fuck them.”
I gave him my address and we talked for another minute before he told me when to expect the clients. After he hung up I stood and laid Virginia back on the water with her head on a cushion along the side.
I started to fuck her with deep thrusts, “You need two bedroom sets Meg and they need to be delivered before six, you also need a box of condoms. There is one other thing, I get to fuck both of you bareback.”
My sister was moaning as her pussy spasmed and kept grasping at my cock. Meg grinned as she stood, “fine with me.”
I buried my cock and held my sister as I began to gush a huge stream of cum. She jerked when she felt warm sperm erupting and pumping into her. She shuddered as her tight pussy milked the cum into her. When I finished I pulled out and stood her up, “go get dressed and go with Meg. When you return I need to loosen your ass in case they want to fuck it.”
She grinned and kissed me and stuck her tongue in my mouth. After they left I sighed and got out and dried off. I cleaning up and got the two empty back bedrooms ready. It was an hour before there was a knock and I let them in and helped bring the furniture up in the elevator. While they made the beds I made a small dinner.
I went to my room and brought out the bottle of lube. Virginia and Meg came out together and I bent my sister over the dinning room table after pulling her skirt and panties down. I put lube on a finger and began rubbing her asshole as she sighed and wiggled. It was awhile before I had a finger buried and was fucking her ass.
A few minutes later it was two fingers and she was moaning and shaking. I opened my pants and Meg helped by pushing them down. I moved behind my sister and pushed my cock into her ass. I fucked her slowly, taking my time and adding lube. It was five minutes before she spasmed as her ass tightened and I buried my cock.
She jerked and twisted and shuddered and wailed. I started fucking her with long, deep thrusts and several minutes later I shoved into her and began to spurt and spew more cum. Virginia stiffened when she felt the warm cum pumping into her ass and pushed back, “FUCK!”
When I was done I pulled out, “now you aren’t a virgin.”
I pulled her off the table and into a chair, “have you given a blow job?”
She nodded as she kept feeling her ass. Meg giggled and Virginia looked at her before grinning. I cleaned up after they ate and sent them to douche and use an enema. It wasn’t long before the doorbell rang and I let Mr Phillips in with eight clients. Meg and Virginia were waiting naked in the living room.
I walked to them and led the men towards the hall and one room. Mr Phillips came out an hour later and grinned as he held out an envelope, “this should be enough.”
I took it and glanced inside to see at least five thousand dollars. I smiled and nodded, “I’ll make sure they get it.”
He looked around and smiled, “if you keep them I can send a lot of business your way.”
I glanced at the hall, “they can start around three everyday except Saturday and Sunday, they can start at nine in the morning then.”
He grinned, “deal.”
After he left I went to put the money away. The men left before nine and I walked back to see a cum covered Virginia and Meg on the bed together. I stripped and reached for Meg and turned her at the edge of the bed and lifted and spread her legs. Her pussy gapped and looked puffy but no cum was leaking out as I pushed into her and started to fuck her slowly.
I used long thrusts and kept planting my cock to grind, “did you call home and tell mom you were staying overnight Virginia?”
She nodded and moved closer to suck on one of Meg’s nipples as I continued to fuck her. Five minutes later she was jerking and convulsing as I buried my cock to pump strong spurts of cum into her. She jerked and shuddered as I flooded her belly and pulled out when I was done. I turned her on the bed before reaching for Virginia.
I rolled her onto her stomach and spread her leg before moving onto the bed and pushing into her. I fucked her firmly with long, deep thrusts. Her pussy was hot and slick from lube she had poured in. It was several minutes before she shuddered and spasmed as her pussy grasped my cock. I began to fuck her with deep thrusts as I tried to cum.
It was several more minutes before I thrust into her and held her as I began to spew sperm. Virginia shuddered when she felt the warm cum pumping into her. When I was done I pushed her into bed and moved to pull the sheet up before turning out the light. I slipped into bed and reached for Meg. I fucked them several times before we slept.
I was up early and went to shower before coming back to rub Virginia’s butt to wake her. She groaned and turned her head, “again?”
I smiled, “you have until three before any clients arrive. Make sure you douche and use an enema, ask Meg to buy both of you anal plugs.”
She rolled onto her back, “my butt is a little sore.”
Meg chuckled, “I’ll get them.”
I nodded, “I left a couple of hundreds on the table. Buy a couple of bottles of lube, another box or two of condoms and the plugs.”
I went to work and had a few calls to fix computers that were full of addware or malware which are pretty much the same thing, a pain in the ass. Mr Lee, one of the firms senior partners stepped into my small office as I was replacing memory in a computer, “Tom.”
I turned, “sir?”
He smiled, “Mr Phillips told me you found entertainment for his clients. They seemed more than happy and I was wandering if they would be available for an afternoon party with a couple of my clients.”
I smiled, “After three in the afternoon on weekdays and after nine in the mornings on weekends.”
He grinned, “perfect, I have to have them back at their hotel by six.”
I wrote my address down and handed it to him before going back to work. I always set my own hours and ended up with two other partners making appointments for that night before I left. I got home in time to change and caught my sister coming out of the bathroom with Meg, “you have three parties tonight. The first should be here in a few minutes.”
It was a busy night and they took a shower and cleaned up after each group and ate. I relaxed and set up a few things like accounts for Meg and Virginia. I had deposited the money from last night and used some to buy company stocks. I was paid by each group when they arrived and the girls made over twenty grand.
I locked up after the last group left at ten and went looking for Meg and Virginia. They were in the shower together and I slipped in to wash them before pulling them both to my bed. They were sore and Virginia pressed against me, “can I ask Sarah if she wants to join us?”
I turned her to Meg, “talk to Meg first.”
Meg grinned, “one more would help.”
I nodded, “She was the one with the alcoholic father and crack head mother?”
Virginia nodded, “yeah, she doesn’t spend much time at home.”
I reached around to cup her breasts, “Is she safe?”
Virginia turned and stroked my cock, “she has had sex a couple of times and always uses rubbers.”
I pulled her against me, “go call her and see if she can come over to talk to you and Meg, this is your idea.”
She grinned and climbed out of the shower and Meg pressed against me, “I was thinking of a girlfriend too.”
I sighed, “call her if you think she is safe.”
I pushed her towards the shower door and followed her out. I dried off and slipped into bed. I must have fell asleep because I woke to hands and a warm, tight pussy forced down onto my cock. I groaned and opened my eyes to see a petite golden haired girl with her pussy stretched obscenely around my cock.
I reached up to cup her breasts and rub her pretty pink nipples, “Sarah?”
She grinned and wiggled as her pussy squeezed my cock, “hi Tom.”
I caressed down her sides to her hips as she slowly rocked and slid back and forth, “are you going to join my sister and aunt?”
Sarah shuddered and lay on me, “yeah, I need money to get away.”
I looked at her as I put my arms around her, “can you stay with me?”
She lifted her head to look at me, “even after I fuck those men?”
I nodded and her pussy spasmed before she shuddered and pulled as she rolled over. I went with her until I was between her legs. She looked up into my eyes, “I’m fourteen Tom, I know I act older but it is just an act.”
I began fucking her, “stay with me?”
She wrapped her legs around my waist, “okay but I want to fuck those men to make money.”
I kissed her before fucking her with deep thrusts. It wasn’t long before she was shuddering and jerking as her tight pussy spasmed around my cock. She was lifting and thrusting up with her hips as she began to wail and I pushed into her completely before I grunted and groaned and began to spew a gushing stream of cum.
Sarah lifted her hips and screamed when she felt the warm sperm pumping into her, “YES!”
It was a few moments before I stopped cumming and kissed her as she panted and kept shuddering, “you can fuck the men but you use protection with them.”
She grinned and hugged me, “but you want me bareback.”
I smiled, “yes.”
Sarah nodded and pushed on me, “I think the other woman wanted to fuck you too.”
I pulled out and moved off the bed, “where is my sister and Meg?”
She grinned, “in Meg’s room.”
I helped her off the bed and took her hand as I went to look for Meg and Virginia. I found them in bed with a woman sitting on the bed talking to them naked. She was a stunning woman with pink nipples. Sarah let my hand go as she walked around to climb in beside my sister. Meg grinned, “This is Kathryn but you can call her Kat.”
I smiled as the woman stood, “you are a handsome stud aren’t you.”
I grinned as I stepped closer and sat her back on the bed before pushing her back as I knelt. She opened her legs as she laughed and Meg shifted to hold her. I smelled her pussy and licking through it before nibbling on her lips. I covered her clit and teased it before licking her again as she shuddered.
I kept licking her and teasing her clit until she finally spasmed and twisted away. I stood and lifted and spread her legs as I leaned forward to guide my cock to her pussy. When I pushed into her she was warm and very tight. She grunted as I began to fuck her slowly with deep thrusts.
It didn’t take her long to howl and start jerking around while her pussy began milking my cock. I held her hips as I fucked her hard and deep, planting my cock each time and grinding. Kat screamed and thrashed around as she wet me. It was a couple of minutes before she was wailing as she bucked and spasmed.
I kept fucking her through several more orgasms before burying my cock and pushing against her cervix. She jerked and looked at me when I grunted and began to spew cum, “yyyyeeeesssss!”
I pumped thick spurts until I was done and sighed before pulling out and turning her on the bed. I sat beside her and rubbed her tummy as she panted, “you use condoms with the clients or any boyfriend, I will fuck you bareback. The hours unless it is just you and Meg is after three in the afternoon on weekdays and after nine in the morning on weekends. That gives you time to rest, it also sets everything up for when Virginia and Sarah go back to school.”
I stood, “I will manage the money and give you your pay.”
She grinned at Meg, “how much are you taking?”
I shook my head, “I haven’t taken anything.”
I headed for the door and she rolled off the bed, “wait, I want to fuck some more.”
Sarah laughed and climbed out, “me too.”
I woke to my alarm and glanced at Sarah and Kat, I had fucked them both three times before we went to sleep. I slipped out of bed and went to shower and get dressed. I barely got into my office before getting a call to head up to a partner’s office. By the time I got off I had three more parties scheduled and had called Meg to let her know the first would start at three.
The men were already there when I arrived and found Virginia bent over the couch while a man fucked her. Luckily the men didn’t last or linger before paying me. I made dinner as they douched and cleaned up and after the second party began I got a call from Mr Lee who wanted to bring three clients by at midnight.
It was almost two before everyone was gone. The girls were tired and both Meg and Kat went to bed. I was tempted to fuck one of the girls but slipped into my bed with Virginia and Sarah. I held my sister and let Sarah put her head on my shoulder. I woke to the alarm I had set and moved my sister to shut it off.
I moved over between Virginia’s legs and kissed her before pushing into her. She groaned and opened her eyes as I began to fuck her nice and deep, “Tom?”
I kissed her, “its seven thirty and you have clients at nine.”
Her pussy tightened as she shuddered and lifted her hips, “mmmm!”
I continued to fuck her as Sarah came to rub my back, “how many do we have today?”
I buried my cock in my sister and kissed her before looking at Sarah, “four men this morning and another three groups this afternoon and tonight.”
Virginia shuddered and hugged me as I started to fuck her hard and deep. She lifted her feet into the air and wailed as I thrust into her and pressed before I started to spew and gush a thick stream of cum. She jerked and clutched me when she felt the warm sperm, “TOM!”
I pumped spurt after spurt until I was done and waited until she dropped her legs and relaxed to pull out. She panted and grinned at Sarah, “I like feeling him squirting in me.”
Sarah pulled on me, “fuck me.”
I grinned as I rolled her onto her stomach and lifted her butt as I pushed her legs together. I straddled her legs and pushed into her before holding her hips and fucking her with long strokes. It wasn’t long before she was shuddering as her pussy grasped at my cock. I continued to fuck down into her after she wailed and started kicking the bed and shaking.
I was fucking her with long thrusts as her pussy kept grasping and milking my cock. It was awhile before I buried my cock and held her as I began to pump cum deep inside her. I kissed her shoulder and neck as I continued to spurt. When I was done I humped and she shuddered and looked back while Virginia giggled.
I pulled out and moved off her and out of bed, “come wash and douche.”
We were in the shower when Meg and Kat joined us. I started caressing and feeling both and my sister laughed, “he is warming us up for a morning with clients.”
Kat shuddered as I rubbed her pussy, “yummy, I love morning sex.”
I lifted and turned her to put her back to the wall as she wrapped her legs around my waist. I lowered her as Meg positioned my cock and she wiggled while I slowly impaled her. I kissed her before starting to fuck and hump into her. She groaned as her pussy squeezed and I began to fuck and plant my cock firmly.
It was a couple of minutes before Kat wailed as she wet me and shuddered. Her pussy tightened and I started to fuck her and hump into her harder. I pressed and jabbed before holding her as I pulled back to fuck up into her. She howled and spasmed as her pussy continued to grasp my cock.
It was several minutes before I lowered her and buried my throbbing cock. Kat was clutching me as her pussy spasmed and I began pumping a geyser against and through her cervix. She shuddered and jerked, “yyyeeeeesssssss!”
I groaned as I spurted a few more times before stopping. I held Kat for a minute as she panted and then lifted her off my cock and set her down. She leaned against me and giggled, “washed on the outside and sperm douched on the inside.”
They laughed and she stepped back and turned to start washing. After showers was a small breakfast and then the men arrived. We ended with an extra few men right before lunch but everything stopped by ten that night. I had been able to feed them lunch and dinner between groups but they were tired when I closed the door after the men.
They had made over a hundred thousand for the day. I stripped on the way to the spa and found all four already there. I sat and leaned back to let the hot water relax me. I had spent the day doing research and accepting a couple of appointments for tomorrow, “you have clients at twelve and five tomorrow. I’ll be giving each of you two thousand tomorrow to go shopping but be back before twelve.”
Kat looked at me, “Only two?”
I smiled before opening my eyes and looking at her, “are you going to spend the money as fast as you make it?”
She grinned, “well no.”
I turned to pull Meg onto my lap, “the money you made the other night I deposited and on Monday today’s and tomorrow’s money will be added and then invested.”
Meg turned and straddled me before slowly sitting on my cock. She sighed and leaned against me, “you know they won’t use us every day of the week.”
I grinned and caressed her hips as her pussy grasped my cock, “I know and on those day you get to relax or shop. I think during the week it will be slow so I was thinking of putting you to work doing something else.”
Meg began rolling her hips as she thrust back and forth while Kat, my sister and Sarah moved closer. Virginia leaned against me, “like what?”
I caressed Meg’s hips again and looked at my sister, “like learning to draw or paint or photography. You will use each other as models and wear gowns or negligees.”
They grinned and Meg bounced, “you are just trying to...”
I leaned back and reached up to tug on her nipples, “make you aware of how you look so you tempt men into returning. If you can keep them coming back I will make you enough in one year so that you never have to work again if you don’t want to.”
They grinned and Meg shuddered and jerked as her pussy squeezed. I rubbed her hips, “can we finish this in bed?”
She grinned and slowly stood before holding out her hand, “I was hoping you would say that.”
I grinned as I stood and took her hand and followed her out and dried us. She led me back to her room and laid back on the bed. I moved over her and kissed her softly as I pushed into her. I fucked her slowly with long thrusts that sank my cock into her nice and deep before I humped and pressed.
I continued to kiss her as I fucked her slowly and it was a couple of minutes before she moaned and shuddered. The others climbed onto the bed and laid back holding each other as I kept fucking Meg. It was a few more minutes before she shuddered and then spasmed as her back arched and she wailed, “aaaahhhh!”
I kissed her as I buried my cock to hump and grind while she kept thrashing around. When she started to relax I went back to fucking her slowly. She grinned and shook me before giving me a kiss. I began fucking her harder with long firm thrusts and she humped up to meet them. A minute later I pushed into her and pressed as I came in a thick spewing stream of cum.
Meg jerked as her pussy tightened and she shuddered while clutching me, “yes!”
When I was done she grinned, “that was so good.”
I kissed her and pulled out and Sarah moved to push me onto my back before straddling me, “you have to sperm me too.”
Virginia and Kat laughed as she wiggled and sat on my cock. I was wrong, it took barely three months to make enough for them to retire. They continued for over a year before quitting, my sister met and married a broker a few years later. Kat, Meg and Sarah still live with me and seem happy now that they have children.