Matt's Story Pt. 05

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Matt submits to a couple of new Mistresses.
4.3k words
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Part 5 of the 5 part series

Updated 05/25/2024
Created 05/05/2024
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Shortly, Mother walked out of her bathroom and I couldn't believe my eyes.  She was wearing a tight, red bustier with her breasts exposed.  It was tight around her waist and my eyes were drawn to the six-inch dildo sticking out from the harness she was wearing.  She stroked it as she walked toward me lying on the bed, wearing high-heeled, red, knee-high boots.

At the edge of the bed, she reached down, and grabbed my hair.  She pulled my face toward her dildo, and said, "Suck it, bitch."

I opened my mouth and took the hard rubber schlong into my mouth.  I started to bob my head up and down on it.  Mother grabbed my head and began to fuck my mouth.  I could smell her sex as she did.

"Oh, yes," Mother said, rocking her hips and pounding into my mouth.  "You are a natural cock-sucker.  That will come in handy."

After some time, she pulled her dildo out of my mouth and told me to get on my knees with my face on the pillow.   I did and now had my ass sticking up in the air.  Mother grabbed a tube from the nightstand and climbed onto the bed behind me, between my legs.

I felt her run her hands over my ass cheeks.  "Such a beautiful ass," she said, "I am really going to love using it."

She slapped my ass hard, then ran her fingertips up and down my crack causing me to moan.  Then pulling my cheeks apart, she ran the tip of a finger over my puckered hole.  "Oh, my, yes," she said, "This is going to be so much fun breaking you in."

She pushed a finger into my tight hole, causing me to grunt.  Laughing, she pushed deeper into me, slowly turning her finger back and forth as she did.  Soon she bumped into my prostrate, and said, "Oh, there it is."  She rubbed it and I really started to moan,

"You like that, don't you slave?" she asked me as she now started sliding her finger over my spot.

"Oh, yes, yes, Mistress," I squealed at her, "That is wonderful.  Please don't stop."  

Laughing, Mother said, "Oh, you are really going to love it when I fuck you."   With that, she pulled her finger out of me and I felt something cool on my ass as she poured some liquid near my hole.  Then she pushed two fingers back into me, and without waiting started finger-fucking me hard and fast.  As her fingers rubbed against my prostrate, I humped back at her hand.  

After some time, she pulled her fingers from me, gave my ass a hard slap and I felt her running the tip of her dildo-cock up and down my crack.  I was panting and squirming.

"Want this, bitch?" she asked.

"Yes, Mistress," I answered, squirming, "Please."

With that, she pushed her dildo cock slowly into me, completely until her thighs were pressed against my ass.  She held it there, running her hands over my ass.

"Now," she said, "I'm really going to fuck you."

She started slamming her dildo-cock into me, hard and fast, holding my hips.  I was grunting and moaning with each thrust, pushing back to meet her thrusts.

I cried out, "Please, Mistress.   Please, can I cum?  Please."  

Laughing, she said, "Yes, slave.  Cum for me."

Without her slowing down, I screamed and shot the biggest load I had ever done until my cock was completely spent. Still, she continued.  Finally, holding my hips, she pushed into me, cried out and I felt her body quake against me.  When she finally stopped, still holding my hips, she continued to slowly fuck into my ass.

She pulled out of me, gave my ass a hard slap and stood.  I collapsed onto the bed, spent.  She pushed me over onto my back and grabbed my spent cock and started to stroke it, hard and fast.

"Please, Mistress," I pleaded, "I have nothing left."  But she just smiled and continued to stroke me, my cock trying to get hard, but not having much luck.

Finally, she stopped, my cock now rubbed red and a bit sore.  Looking into my eyes, she said, "It is always about what I want.  This is only for my pleasure, not yours.  And I will do anything I wish to do, regardless of your wants.  Now, leave.  Go to bed, bitch."

I stiffly climbed out of her bed and slowly wobbled up the stairs to my room.  My head was spinning as I tried to make sense of why I loved being dominated by my kid sister, my Mother, and other females.  As I thought about Mother just fucking me, even though my ass was a bit sore, I started to get turned on.  

I walked into my room, and Mary followed me in.  I glanced over and saw the red light blinking on the camera, and then saw the belt she was holding in her hand.

"On the bed on your belly, slave," she commanded.

"Please, Mistress," I begged, "I am so tired and sore."

Mary laughed, and said, "I don't care, slave.  On the bed.  NOW."

I lay down as she ordered, and buried my face in my pillow.  She pulled my head up and said, "No need to be quiet now, bitch.  Scream if you want."

I screamed as she brought the belt down hard on my ass.  She gave me ten hard slaps with the belt, as I squirmed and screamed with each one.  Then she reached down and ran her hand over my very sore ass.

"Nice," she said, "It looks better now."

"Thank you, Mistress," I sobbed as she turned and left.  I rolled over onto my side and looked at the blinking camera. I reached down and slowly stroked my hardening cock and drifted off to sleep.

I woke in the morning to someone stroking my hard, morning wood.  Slowly opening my eyes, I saw Mother sitting on the edge of my bed, her hand slowly stroking me.  I moaned and said, "Good morning, Mistress."

Giving me a smile while she continued to stroke me, she said, "Good morning, slave.  How do you feel this morning?"

"Wonderful," I said, squirming under her stroking hand.

"Did you like getting fucked?" she asked, letting her free hand run over my chest and belly.

"Yes, Mistress," I said, looking into her eyes. "It was wonderful."

Giving me another smile as she continued to stroke my cock, she said, "Good.  This weekend your Sister Mistress is going to enjoy fucking you too.   Do you want to cum now?  Beg."

"Please, Mistress," I moaned, lifting my hips, "Please let me cum.  Please."

Laughing, she said to me, "Okay, slave.  You may cum."  As she worked my cock harder and faster.  

Just then Mary walked into the room, watching as I shot a big load onto my belly and chest as Mother continued to stroke my cock.   Finally, spent, I collapsed down onto the bed.  Mother squeezed and milked the last drops of cum from my cock, coating her fingers.  She brought her hand to my mouth and without a word, I opened my lips and let her push her sticky fingers into my mouth, which I licked clean.

Standing, and seeing Mary standing there, she gave her a hug and said, "Good morning, honey.  I think you have done an excellent job of starting his training."

"Thanks, Mother," Mary said walking over to my bed.  "I'll let him clean up this mess."

Mother watched as Mary scooped up some cum on my belly and fed it to me, my tongue licking it from her fingers. Mother continued to watch for a few minutes and then left, saying, "Come down for breakfast when you are done."

After feeding me the last of my cum, Mary stood and said, "Take a shower and come down for breakfast.  Play with yourself in the shower, but do not cum."

With that, she left.  I went to the bathroom, noticing the blinking red light on the camera.  I stepped under the warm water and washed my body with soapy hands.  Then turning so the camera could see me clearly, I started stroking my cock, soon getting it hard.  Remembering her words about not cumming, I stopped and climbed out of the shower to dry off, my hard cock swinging in front of me.

In my room, I dressed.  My usual outfit now, a pair of chinos and a sports shirt, no underwear.  Mary had removed all of my underwear from my dresser, so I had none to put on.  Putting on a pair of loafers, I headed down to breakfast.

As I walked into the kitchen, Mother was standing at the sink and when she saw me, her eyes got big and she screamed at me as she strode toward me, "What are you doing dressed?"

The look in her face was one of anger and I mumbled, "I had to dress for school, Mistress."

As she walked up to me, she drove her knee, hard, into my groin.  I cried out and slumped to the floor.

"Not until you are ready to walk out the door do you get dressed," she yelled at me.  "Now get up and get those clothes off.  You barely have enough time to eat."

I slowly got to my feet with Mary laughing at me.  I pulled off my shirt and dropped my pants to stand naked in the kitchen.

"That's better," Mother said, "Now stand there and eat."

I stood at the edge of the table, eating my bagel and having some juice while Mary fondled my cock.  When I was done, it was time to go to school, dropping Mary at her high school along the way.  I pulled on my pants and shirt, again.  As I started to the front door with Mary and Mother following, Mary told me to stop.

"Take it out, now," she said.

I unzipped my pants and fished my cock out, which was now starting to get hard again.  I knew by the time I dropped Mary at her school it would be completely hard.

We went out the front door and started down the sidewalk to my car.  Mother stepped out onto the porch, a big smile on her face.  Just then Mrs. Jacobs next door walked over, giving me a long stare.

She walked up to the porch and talked to Mother as Mary and I got into my car and drove off, with Mary's hand wrapped around my now hard cock, slowly stroking it.

Stopping in front of Mary's high school, she looked at me with a big smile, while continuing to stroke my cock.

"A long weekend, slave," she said with a sneer. "And Mother is going to show us a lot of new things.  I am really excited, it is going to be so much fun."

"Yes, Mistress," I said, trying hard not to cum.

"I'll bet your balls are really full, aren't they?" she asked.

"Yes, Mistress," I replied, "I am going to need to cum soon."  As I squirmed in my seat.  

Laughing and finally removing her hand, she said, "Don't you even think about cumming.  You will be severely punished if you do."

She opened the door to get out, I looked at her and said, "Yes, Mistress."  A few students and teachers passing by had a nice view of me sitting there with my hard cock sticking out of my pants.  

My day at school was very difficult.  I could not keep my mind on my studies and had a hard time trying to keep my cock from staying hard and leaking in my pants.  Having no underwear on, it presented an obvious wet bulge in the front of my slacks.  I tried my best, carrying a book in front of my pants anytime I had to stand and walk.

After my English class, as I was walking out of the room, my Professor, Mrs. Carman, called to me.  "Matt, may I have a word with you?"

I stepped to her desk where she was sitting as the last student left the room and the door automatically closed.  

"What is going on with you?", she asked me.  "You seem very distracted lately."

Blushing, I just stammered, "Nothing.  Just some things on my mind.  I am sorry I am not paying attention in class."

She looked me up and down, then said, "Let me see that book."  Holding out her hand.

Not knowing how to avoid handing her my textbook, I did.  Her eyes fixed on the front of my slacks, eyeing the bulge and wet spot at the top of the bulge.

She smiled and said, "I know you Mother quite well. I think I might have to give her a call."  She picked up her phone and made the call.  She put the phone on speaker so I could hear the conversation.

"Susan, this is Marge Carman," she said.  "It has been a while since we've had you over to the house."

I could hear the delighted surprise in my mother's voice.

"What a wonderful surprise," Mother said.  "Yes, Marge, it has been way too long.  How is your wonderful subby husband?"

Giving a chuckle, Mrs. Carman said, "Oh, he is fine.  He could use some of your special discipline.  It has been a long time."

"Far too long," Mother said, "Maybe I should stop by soon and take care of it."

"Please do, it is so much fun," Mrs. Carman said. "But what I'm calling about is Matt."

"Okay," Mother said, "What has he been doing?"

"Well," Mrs. Carman said, staring at my crotch, "He has not been paying attention like he usually does.  And I think I know why.  He is standing here in front of me with a large bulge in his slacks and a wet spot at the top of the bulge.  I do believe his mind is elsewhere."  She gave me a big smile when she said that.

Mother gave a short laugh.  "I can imagine what that slave is thinking.  Marge, maybe you'd like to help out and take care of his problem.   Matt, you do anything that Mistress Marge tells you or you will be sorry when you get home."

"Yes, Mistress," I said with a red face.

"Okay, Susan, I will be sure to take care of it," Mrs. Carman said, reaching forward and squeezing the bulge in my slacks.

"Thanks, Marge," Mother said, "Let's all get together real soon."   And hung up.

"Okay, slave," Mrs. Carman said to me, "Drop your pants."

"Yes, Mistress," I said, unfastening my pants and letting them fall.

"Oh, my," Marge said, staring at my hard cock, "Such a nice, hard one.  No wonder you were having trouble." With that, she wrapped her hand around my cock and started stroking.  

I moaned and thrust my hips toward her.

"Do you want to cum, slave?" she asked me, one hand cupping my balls while she continued to stroke.

"Yes, Mistress," I moaned, "Yes, please.  I need to cum.  Please."

With a chuckle, she said, "Okay, slave.  Go ahead and cum."

As I started to spasm, she took the head of my cock into her mouth and she swallowed as I shot my load.   Finally, I was spent, standing there panting, while she continued to hold my cock with the head in her mouth.

"Thank you, Mistress," I mumbled.

Sitting back in her chair and looking at me, she said, "Okay, pull up your pants."   She stood and walked toward the door and opened it.  After I pulled up my pants and walked toward the door, she stopped me with a hand on my chest.  

"I'll make sure your Mother brings you over to my place for a visit," she said, "She is lucky to have such a good slave as you at home."

I finished my day of classes and headed to my car. As I started up, before heading to pick up Mary, I fished my hardening cock out of my slacks.  I drove over to the high school getting more excited by the minute.

Mary walked out of the school and toward my car, talking to Irma and another girl.  They laughed as they walked.  I had a book covering my now hard cock.  As she got to the car and opened the door, Mary said to me, "Ditch the book, slave."

Without hesitation, I said, "Yes, Mistress," and tossed the book into the back seat, exposing my hard cock sticking up out of my slacks.  Both Irma and the other girl giggled.

Irma said to me, "I wish I could ride home with you, slave."

"Me too, Mistress Irma," I said.  The other girl stared wide-eyed.

Mary climbed in and said, after closing the door, "Okay, slave.  Home."  As she wrapped her hand around my cock, giving the two staring girls a good look.

I always drive faster going home, with excited anticipation of what was to come.  Mary noticed, "In a hurry to get home?" she asked.

"Yes, Mistress, to serve you," I said with a touch of excitement in my voice.

Mary laughed and said, "You might regret that thought."

We pulled up in front of our house and got out of the car.  I walked around the car, my hard cock sticking out in front of my slacks, and followed Mary up the walk to the door.  I was grateful that no neighbors were outside to see us.

Stepping into the foyer, Mary turned to me and said, "Strip, slave."

I immediately took off my shirt, dropped my slacks, and stepped out of them and my shoes until I stood completely naked in front of my kid sister, my hard cock pointed at her.

She smiled and said, "Go get the mail."  I opened the front door and stepped out onto the porch just as Mrs. Jacobs walked up to the steps.  I froze, my heart sank as she stared at my naked body.  Excited, my cock spasmed and twitched at her stare.

Mary stepped out onto the porch and said, "Well, hello Mrs. Jacobs.  So nice to see you", as she stood next to me, her hand sliding down to wrap around my hard, leaking cock.  

Mrs. Jacobs gave a big smile, her eyes never leaving my naked body, and said, "Hi, Mary.  Nice to see you two.  I had a nice talk with your Mother this morning.  She said if you needed any help to discipline your slave, I was to offer.  So, do you need help to correct your slave?"   And she gave Mary a big wink.

"Why, yes I do," Mary answered, as she fondled my cock, "He has been bad and needs to be disciplined.   Can you help me with that?"

"Of course, honey," Mrs. Jacobs answered.  "It would be best if we went to my house so I can really help you."

"Perfect," Mary answered, "Let's go, slave." With my face turning more red from the humiliation, I followed Mary down the steps.  Mrs. Jacobs wrapped her hand around my cock, and pulling me along, said, "This way.  I have just what we need to discipline this bad boy."

We walked into Mrs. Jacob's house, where I had been many times growing up, and headed down to the basement.  Both Mary and I were shocked by what we saw since we had never been there in our previous visits.

A bench, a large wooden X frame, and many items of discipline and bondage hanging on the walls.  I gasped and my cock twitched, anticipating what might be happening.

"Over here," Mrs. Jacobs said to me, pulling me by my cock.  "Stand right here.  Raise your hands above your head."

Mrs. Jacobs went over to the wall and removed a few items.  Walking back over, she handed Mary what looked like a leather-covered board with a pair of restraints on each end.

"Get him to spread his legs and attach these to his ankles," Mrs. Jacobs told Mary.  "They will keep his legs spread."

She grabbed my left wrist and snapped on a fur-covered handcuff with a ring attached to it.  Then she did the same to my right wrist.  She clipped on one of the lines hanging from the ceiling to my left cuff and then did the same to the one on the right.

Meanwhile, Mary knelt behind me, pushing my legs further apart, and then attaching the board between my ankles.  My legs were now spread apart and locked into place.

Mrs. Jacobs went over to the wall where there was a switch.  She held the switch open and the lines from the ceiling started to rise.  They pulled my hands up until I was standing, legs spread, on my toes.  Then she stopped and smiled at me.

"Come pick out something you'd like to use," Mrs. Jacobs said to Mary, who walked over to her by the rack on the wall holding all of the implements.   After picking up and discarding a few, Mary settled on a tawes.  Mrs. Jacobs said, "Good choice. I'll take this," as she lifted a cane from the shelf.

Walking back over to me, she said to Mary, "Give it a try."

With a smile, Mary smacked my ass with her tawes.  I yelped and jumped, being restrained.

"Oh, honey," Mrs. Jacobs said to Mary, "You need to be a lot harder than that if you want him to scream.  Try again."

This time Mary smacked my ass with the tawes as hard as she could and I screamed and jerked.

"Yes, that is better," Mrs. Jacobs said.  "What do you think, six each?"

"Well, he was very disrespectful to you," Mary said, "How about eight each."

Laughing, Mrs. Jacobs said,  "Good girl, you are a perfect Domm.  We will alternate strokes."

With that Mrs. Jacobs hit my ass hard with her cane, bringing forth another scream from me.

The two of them settled into a quick rhythm, alternating blows on my ass and the back of my thighs, causing a scream from me with each.  And my cock really betrayed me, twitching with each shot and leaking a large amount of precum, dripping to the floor.

Finally, they were done.  Tears ran down my cheeks and my ass and thighs were on fire.  But my cock was near bursting as precum continued to leak.

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