Trust Fund

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

As, I followed Martha to the dining room, I could feel the suppository slipping around my anal canal and it felt kind of warm. A little warmer than my natural body heat as if it had a warming element to it. As my ass swayed back and forth with the movement of me walking behind Martha, my pussy started to betray me again. The warm sensation in my ass was making my pussy throb, and when my pussy throbbed it created juice!

Again the dining room was bigger than my whole apartment and had a table bigger than most people's car. As we entered the room, I caught my breath. This man, my uncle was the most handsome man I had ever met!! He was ruggedly handsome and looked like he belonged on a ranch or something. His tan skin reflected an active lifestyle and his dark hair was gray at the temples only adding to his handsome look. He looked strong and healthy, and nothing like I imagined when I thought about him. He looked like his son only slightly older.

Suddenly, I felt very embarrassed to be wearing such a slutty outfit to dinner. My cheeks were hot and my gaze fell to the floor in shame as I followed Martha to an empty chair to the left of my uncle. My cousin was across from me at the right hand of his father. I briefly looked at my uncle trying to get a reading on what he thought of my attire, and his face was that if a kid in a candy store. I was shocked such a slutty looking woman joining him for dinner would excite such a handsome and distinguished man. The dining room was beautiful with candles lit and beautiful china before us. After I was seated, Martha took the only other empty chair at the table, opposite my uncle and very far at the end of the table. I doubt she would even hear normal conversation, and I wondered why she was so far away from us.

I unfolded my napkin and placed it into my lap, one of the few forms of being polite and cultured that I knew, and my uncle started talking. He said, "Kendra, I'm so happy you have decided to join our household." "Has everyone been kind to you so far?"

I glanced at Martha and thought of her threat to tie me up and gag me if I didn't obey her, but then I thought about the orgasm I had. I felt the shame of being brought to orgasm without my minds consent. So, I replied with a simple, "yes."

He smiled and said, "Very good, I'm glad to hear it." "I'm pleased with your presents so far, and I look forward to starting my healing treatments." "I'm told it will start two weeks from now at the latest." He looked directly at me.

Was that a question? I wasn't sure how to respond, so I just said, "Yes, that's what I was told too."

He said, "I know all this is very unusual and complicated, just know that I really appreciate your presence and the healing properties of your breast milk." "It is my hope that you grow comfortable with this arrangement and even come to enjoy it." "It has been a very long time since I have had the company of a beautiful woman in my house." "You look very sexy tonight." He smiled, and with that dinner was served.

It had been several days since I accepted the strangest proposal I had ever heard, I was living in my uncle's house, and I was being prepared to breastfeed him. It was 6am, and Martha would be here any minute to stimulate my breasts, everyday I hoped my milk would just come; I was tired of having my breasts fondled and squeezed. Usually I loved having my nipples touched and pinched, but this was more for a purpose, and my pussy didn't get it. Since I had arrived my body was in a constant state of arousal, my pussy had never been given the chance to "dry up." Nor was it allowed to impale itself on a big cock and cum like I wanted to. I had been masturbating whenever I had the chance, but I needed a man inside me to fulfill my desire.

Martha had arrived to stimulate my breasts and help the milk flow, and it started as usual. I removed all my clothes and stood in the bathroom with my fingers laced behind my head, she pinched my nipples and squeezed my breasts. Today a tiny white spot formed at the very tip of one of my nipples and she smiled wide. She said, "very good!!" "Tonight your uncle will suck this milk from your breasts!!" "We will do suppositories for the rest of the week, but it looks like everything is working well." She gave me my daily enema, and I wondered how long before that would stop."

She picked out my clothes, and left, as was her usual routine. I climbed on top of the big bed that was covered with my own comforter, as my stuff had arrived yesterday and I was still unpacking. I was on my knees and ready to plunge two fingers into my sopping wet pussy when Martha appeared again. She was scowling and said, "I was wondering of you had been doing that without me."

I said, "thanks, I can do it by myself." I wished she would leave, as it would only take me 60 seconds or less to cum.

She had a funny look on her face, and she walked directly to me. She lifted her arm to reveal that she was carrying a strap on dildo. I'm sure my eyes got big, as my mind started to wrap itself around what she was offering. She moved her hand and the strap on just swayed back and forth as a teasing gesture. I had kissed another woman, but I had never "had sex" with another woman. Martha said in a deep throaty voice, "from now on, you will not cum unless I give you permission." "Do you understand?" I nodded in compliance, and again I was warned by something scary in the tone of her voice.

I carefully thought about her words as she removed her clothing. Her nakedness revealed a very tight body; her face had aged before her body had. Her tits were nice and round and I wondered if she had ever had children. She had a flat belly and no stretch marks; her body was gorgeous!! She was pulling the straps tight and the rubber cock stuck out like it was ready to fuck me. She got onto the bed and was on her knees when she asked, "Kendra, do you want to cum for me?"

I rolled over and spread my legs, and said, "Yes, I want to cum."

She positioned herself between my thighs and probed the opening of my pussy with her strap on dildo, and I couldn't wait for her to just shove it in. She stopped for a minute and put a pillow under my ass lifting my pussy slightly, she rubbed the wet lips of my cunt and again positioned her rubber cock for penetration. She slid it in very slowly. I couldn't take it any more, I grabbed her ass and started fucking her. I was pulling her into me, and forcing that fake cock to fuck me. My orgasm built very quickly, but I knew it would be better if I waited for another minute or two. I rode the edge of my orgasm briefly.

"Okay, cum for me girl!" she commanded, and I came with such force that I almost passed out. The humiliation of getting fucked by a woman had me turned on beyond anything I had ever experienced. My orgasm lasted several seconds, and the bliss would last all day.

I opened my eyes and she was looking at me with a smile and asked, "do you feel better now?" She continued, knowing I was listening to her every word, "that is the last time you will cum this week." I blinked realizing it was only Thursday, and I wondered if her week started on Monday or Sunday.

She leaned back on my bed and spread her legs wide giving me full view of her light brown pussy lips. She placed the tips of her fingers on her clit and started to rub. She lifted her head and said, "Start licking girl!"

I briefly wondered what would happen if I didn't do what she asked, but then I started to feel guilty because she had just given me a fantastic orgasm that I had been longing for since I got here. So I moved my face closer to her naked pussy and stuck my tongue out. I licked up and down her slit, the taste of her sweet juices started to turn me on again. Her soft moans and sweet sounds urged me to do more. I sucked part of her pussy lips into my mouth and swirled my tongue around, then I went for it. I stuck my tongue out as far as I could and inserted it into her wet pussy. I started to fuck her hole with my tongue, and she started saying things in Spanish. I understand Spanish enough to know she was saying good job my love, and sweet things she would say to a lover.

She grabbed a handful of hair and buried my face in her pussy; I could hardly breath as she humped my face. Her whole body started to quiver, and all of a sudden I could feel the flow of her cum as her orgasm ripped through her body. She released my hair and relaxed as her orgasm subsided. We both lay on my bed and relaxed for a few minutes. She turned to me and said, "I'm so glad you are here."

"Breakfast will be in an hour" she said and left.

I lay on my bed wondering exactly what was going on in this house. How was I going to breastfeed my uncle and fuck his son's nanny and keep my sanity all at the same time? I decided to think about it later, and got into the shower. I washed Martha's cum off my face, and my cum off my pussy. I dried off and dressed. This time my out fit barely covered my breasts. My tits were starting to feel full and kind of sore and uncomfortable, and this top was displaying their swollen nature very well. It was a white button up shirt, and it was cut very low, so low that I had to push my nipples down and tuck them into the shirt. I laughed at the thought of "tucking my nipples into my shirt." This time I got to wear shorts, but again they did not cover my ass cheeks, and the heels seemed to be getting taller.

Martha appeared to escort me to breakfast, but this time when we left my living quarters, my uncle was in the hallway to greet me. He said, "Good morning Kendra, you look beautiful as always." I thanked him. He said, "Will you walk me to breakfast?" "Do you know how to get to the dining room from here?" I told him that I did, to which he simply said, "Good, I'll follow you."

I felt quite strange walking in front of my uncle who was in a wheelchair and the perfect height for inspecting my ass as it fell out of the shorts he provided me, but like everything else weird and unusual here I just did what I was told. I started to walk kind of stiff and awkward hoping to reveal as little as possible, but it wasn't working. So, I just relaxed and walked like he wasn't there. He immediately noticed the change in my attitude, and said, "That's it, walk like you want me to see that sweet little ass of yours." "It's so nice to have something sexy to look at again."

My cheeks flushed, and I felt sexy all of a sudden. The encouragement and approval felt wonderful, and I felt a different kind of confidence at breakfast today. However about half way through breakfast my tits started aching and throbbing. They felt swollen and were getting sore. Breakfast was finished and I was relived, I wanted Martha to do something to make them feel better. Over the past week, and especially after this morning, I trusted her. My uncle escorted me back to my room and I strutted out in front of him again. By the time I got to my room my shirt was wet, and my tits felt like they were going to explode.

It felt like forever before Martha got there this time, but she was right on time. I was already naked and in the bathroom when she got there. When she joined me a wet little stream had formed and was dripping on the floor, and her eyes lit up. She reached out and squeezed my nipple and milk shot at the wall across from us. She looked into my eyes and asked, "How to they feel?"

I started to cry and exclaimed, "they hurt!" Tears were streaming down my cheeks, and I felt a mixture of relief and shame and I cried to her. She squeezed my tits and rubbed my nipples. She told me to wait for a few minutes; she was going to help me.

I felt like I stood naked in my bathroom for hours, but she returned within five minutes. She said come with me, and I followed her to the door of my living quarters. She was just going to lead me naked through the house with my nipples leaking milk all over the floor. I stopped at the doorway. She looked at me and asked me to follow her; I just stood my ground.

She said to me, "What are you waiting for?" "Your uncle wants to give you some relief."

I said, "But I'm still naked."

She replied, "he wants you naked when he breastfeeds." "You have two choices, get dressed and remove your clothes when you arrive in his room or just follow me now."

"I'll get dressed before I leave the room," I asserted. With that I picked up the wet shirt from breakfast and tried to tuck my breasts into it as best I could, but the had swelled even bigger since the last time it was on. My nipples hung out just like my ass hung out the back of the shorts I was wearing. I quickly followed Martha leaving a trail of breast milk on the floor everywhere I went.

She opened the big double doors to his room and he was in a bed on his side. Martha instructed me to remove my clothed and get into bed with him. I quickly did as she asked sensing there would be relief for my aching tits soon. I looked at my uncle on the bed waiting for me to join him, and dismissed the queasy feeling that this was sick and wrong and got on the bed. Martha helped me position my body so he would have access to my nipple closest to him. He looked me in the eye and said, "Thank you my dear, I know this is going to work."

He slowly sucked my large, dark pink nipple into his mouth. The warmth of his mouth and the gentle pull of him sucking felt wonderful. My other nipple started to squirt as my milk started to "let down." He simple pinched off the flow and sucked eagerly at the one that was in his mouth. The strange feeling of his warm mouth deflating and relieving the pain in my breast made my disobedient pussy start to ache again. I could feel the moisture collecting between my thighs, and the thought of the taboo nature of what I was doing with my uncle made my pussy start to burn. It took about twenty minutes for him to empty the breast he was working on, and the emptiness felt wonderful. I moved to the other side of the bed and Martha helped him roll over so he could empty the other side.

After my uncle had drank his fill of breast milk I was dismissed, as he had some meeting to attend. I picked the mysterious shirt of many sizes and put it on with ease now that my breasts had deflated. The shirt fit fine again and I tucked my nipples in and walked back to my room. Somehow Martha was there already. She said, "I'm just here to remind you that you may not cum unless I give you permission." "You may touch yourself as much as you see fit, but no cumming." She added, "I'm not usually this patient, but in your case I can tell you will need sometime to adjust." "I'm only asking for three days, and I will punish you of you don't follow the rules." She turned on her heel and left.

I quickly climbed on my bed and masturbated till I came and fell asleep.

Martha awakened me, and I had no idea how long I had slept, but I felt groggy when I opened my eyes. She was not happy, she said, "I see you have no respect for me or my kindness, now you will be punished."

I sat up wondering how she knew! How did this woman know I came after she left, but I didn't have time to think anymore? She clicked a handcuff around one wrist and dragged me out of my room. To my horror I was naked still, I struggled, as I knew this woman couldn't be stronger than me. Somehow both my wrists were locked behind my and she was leading me down the hallway like a cop with an unruly criminal.

I was naked and bent over at the waist with my wrists locked together in a set of handcuffs and lifted high in the air to keep me from struggling too much. She marched me into my uncle's room completely naked, and I was horrified! I had felt humiliation several times since I came to this house, but this was far worse than anything I had experienced yet. Martha shoved me towards his bed, and I fell to my knees.

She swiftly unlocked my wrists and repositioned the cuffs so my arms could reach above my head. She pulled me to my feet and my locked wrists together in front of me, and then hooked the cuffs to something suspended from the ceiling. She moved with the precision that told me she had done this many times before, every movement was calculated and efficient. Martha put cuffs on my ankles and locked them to a spreader bar so I stood naked and on display to my uncle and Martha.

Until now I hadn't said a word. I was feeling a mixture of panic and lust, but I was sure I had, had enough and I said, "I think I want to move out."

Martha's head snapped towards me, and she said, "Choose your words carefully." "Tomorrow will be one week that you have lived here, and you will receive $3,000, and $3,000 will be deposited into an account for your baby." "Are you sure you are willing to give that up?"

I blushed at her familiarity of the exact arrangement I had with my uncle. I said, "I do not want to get hurt."

Martha asked, "Have I hurt you?" "Are you hurt right now?"

I answered, "No, but I don't like this."

She said, "You poor sweet thing, you like this very much, and she ran her fingers up my thigh to my treacherous pussy that was mutinying against me and creating a slimy trail down both legs, and chuckled in my ear. She put her fingers to my lips and said, "see, you are liking this very much." "However, I will stop right now if you want." "Tomorrow you will receive $2,000, and $2,000 will be deposited into the account for baby."

She stood behind me and plunged two fingers into my pussy and ran them up my crack towards my asshole and she whispered in my ear, "if you want me to stop, your safe word will be trust fund." "Do you understand?" I nodded my head, and she said to repeat the instructions. If I wanted her to stop what she was doing all I had to do was say, "trust fund." I hated her right now. How dare she use my baby's future to hold me hostage emotionally so she could screw me!! Literally.

As angry as I was, my pussy burned with lust, and that fuelled my anger. I was going to have to figure out how to get out of this the old fashion way. I needed leverage.

Smack!

I was snapped back to reality when my ass was suddenly on fire.

Smack! Smack!

I hardly had time to react; I didn't even know how to react.

Smack! Smack! Smack!

Then Martha started to talk to me, She said, "I am punishing you for disobeying me and cumming with out permission." She was rubbing something cool and hard on my ass in a circular motion, as she was talking to me.

Smack! Smack!

Those two were the hardest ones yet, and I cried out, "ouch!"

Smack! Smack!

She said, "That was ten." "If you do it again I'll give you twenty." "Next we will address your sloppy wet pussy."

I had no idea what she had planned, but I didn't think I would like it. She pushed a table towards my position in the middle of the room, and towards my belly so I was bent over the table with my ass and pussy pushed out and on display for Martha and my uncle. Martha didn't touch me for a few minutes and I could hear her at my uncle's bed. Then I heard the hum of his wheelchair. I was mortified to see him come into view.

He leaned towards me and said, "I do hope you like to be as rebellious as I think you are." "I feel more turned on and sexually charged than I have in years." He wheeled back, and said quite loudly, "Thank you, please continue Martha."

My heart sank; I was hoping to have his sympathy. I was hoping he was somehow understood my misery and I could count on his kindness, but at that exact moment I realized Martha was doing this for him! Not herself, but to please him.

Suddenly, I could feel my ass hole being probed. Her finger was rimming the hole and shoving lube inside. I could feel pressure being applied, and my hole being stretched. It was being stretched bigger and bigger. It started to burn and I knew it would split open at any moment, and the pressure stopped. No more no less. The burning continued, but my ass actually was accommodating whatever huge thing she was trying to stuff into it.