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A Visit to a Mistress – by fun4all6969 (edited)

I have always craved humiliation ever since I was with a girl who humiliated me for my premature ejaculation and my small penis. I saw an ad online for a girl who loves submissive guys and we chatted back and forth for about two weeks before my business trip took me to where she lived. She told me it would be two-hundred and fifty dollars for the domination session and that I had to prepare myself for two weeks without cumming. I shared with her my fantasy of her being my sexy co-worker who finds my stash of kinky porn. I also mentioned I would like to try forced Bi but she did not currently have a guy that she worked with. She had two rules: I could only touch where she approved, and she would not get naked.

The day of the trip arrived. I checked into my hotel and that evening nervously went to the address provided at a nice apartment building. She buzzed me in and up I went to her door. When she opened the door in a red plaid mini skirt and bra, I thought I had died and gone to heaven. Her breasts were the perfect size for me, round, and full, and large, but not too big. She gestured me in.

As soon as the door closed, she turned to me and sharply said, “I found some nasty ass stuff on your computer. If you don’t do everything I tell you I’m going to tell the boss. Now strip and show me what you look like.”

“Please don’t tell my boss,” I said blushing. “I’ll do anything you say.”

I quickly stripped and stood before her naked. She looked at me and laughed. “Well, you’re fucking ugly, and your shrivelled up cock is so tiny. I can’t believe your wife ever fucks you.”

I admitted that she didn’t. “It takes her longer to clean up afterwards than our fucking lasts,” I said.

She laughed again. “You can call me Mistress or Mistress Tessa.” She tossed me a pair of aqua coloured panties, saying, “And put these on so I don’t have to look at that shameful clitty-dick. That’s the smallest dick I’ve ever seen in my life.”

I stepped into the panties as she went and sat on the couch. “Crawl over here, you sissy slut,” she ordered. When I got to her, she stuck the heel of her boot out, and said, “Suck it.”

I did as she asked and sucked the five-inch heel all the way as she laughed and took pictures with her phone. “Lick my boot, top and bottom, bitch.”

I did so, and I was in heaven, stroking the boot and licking it, while she just sat there disinterestedly texting. “All right, that’s enough. Take off the boots and massage feet and calves. If you do a good job, I will let you suck my toes and lick my legs.”

I worked hard and she moaned a few times. “Mmm… You’re a good boy and worthy of sucking on my toes,” she murmured, leaning back on the couch.

As I sucked, I let my hands roam half way up her thighs. She instantly slapped my hand away. “How dare you! Stand up, fag.” As I did she laughed and pointed at my large precum stain on the panties. “Take those damn things off and put them in your mouth, then bend over the coffee table.”

I obeyed, saying, “Yes, Mistress.”

I heard her rummaging around in the next room, and her footsteps as she re-entered the room. All was silent for a moment, there was a sudden swoosh, and a huge paddle hit my ass. I jumped about a mile high and screamed out through the panties as she hit me again and again.

“This is my old sorority paddle,” she said a little breathlessly. She kept it up for a very long time. “All right, I think your ass is red enough. Now sit down on the floor until I come back.”

It hurt like hell and I hoped she came back soon. It couldn’t have been long, but it seemed like forever when she finally walked in wearing a seven-inch strap-on dildo and carrying something in her hand. That something turned out to be lipstick. “Pucker up,” she said, as she painted my lips red.

“All right. Suck it you sissy fag,” she commanded.

I eagerly sucked it and could only down about five inches. She noticed right away, and grabbed my head and fucked my face, causing me to gag and several times almost vomit as she laughed. After about ten minutes of this, she pulled out of my mouth, put a condom on the strap-on and put on a glove. She then forced me to turn around and used the gloved hand to lube my ass before forcing the cock deep in my ass in one stroke. I whimpered as she did so.

As she fucked me hard, she snarled, “Grab that bowl and put it under your pathetic cocklette and jerk off into it.” I did as instructed and I came on the second stroke, she laughed, saying “Wow, you are pathetic.”

My orgasm was powerful and seemed to go on forever and when it finally ended, she pulled back on me until my face was right over the bowl. She smiled evilly. “Lick it all up, fag boy.”

But I could only touch it with my tongue as the desire to eat it up had ended. She grabbed my balls with her gloved hand and squeezed as she repeated, “Eat it all up, you fucking loser.”

I buried my face in the bowl and started licking, but it still wasn’t fast enough for her. “I’m sorry, Mistress, there’s too much for me,” I whimpered pathetically.

Abruptly she pulled the dildo out of my ass. “Flip over on your back,” she commanded. When on my back, she grabbed the bowl with her gloved hand, and said, “Open wide, sissy boy.”

As her knee were pressing on my balls, I obeyed. I opened my mouth as she started pouring the watery cum in my mouth and all over my face.

She laughed, and said, “Get up, and look at yourself in the mirror.”

I saw my face covered with cum.

“Clean yourself up. No, use your fingers,” she said, as I looked for a towel. I scooped cum into my mouth until all that was left was dried cum. She then pointed to some drops on the floor and I knelt down and licked it up.

She tossed me my clothes, and said, “I expect you back here on Friday with five hundred dollars, I have some fun planned for you.”

*****

The week went by so slowly and I was on edge every day. Friday at five pm prompt, I was at her door and she answered, dressed in black boots, short black skirt and a bikini top. She gestured me in without speaking and made me stand in the middle of the living room. She blindfolded me, making sure it was secure. Then she had me undress and helped me into a pair of panties, a skirt, stockings and a bra. Lastly, she put lipstick on me and then tied my hands behind my back.

I then heard her calling out, “You can come out now.”

I heard a door open and then a gasp and a lot of whispering. Whoever it was did not expect what she saw.

Mistress Tessa said, “Sissy fag, we have a treat for you. My friend here brought two condoms that she tied and stuck in her pussy to keep them warm for you to eat. After you eat all the cum you will be able to lick the condom and taste her pussy juice.”

I licked my lips, and Mistress said, “See how much the sissy wants it? Oh, and I also have a condom from my fuck buddy fucking me last night that I left on the bedside table. I wasn’t as nice and didn’t keep it warm. So! Beg for the condoms, fag!”

I begged as they laughed at me. I opened wide as each condom was poured into my mouth which I had to hold open for a picture before swallowing. The first two were nice and tasty, but the last one was gross and I gagged. I was allowed to lick the condoms tasting rubber and some pussy juice.

Then I was led over and roughly pushed down. Mistress said, “I need you to admit something, fag. Last time you took my strap-on so easily in your supposed virgin ass, I think you have practiced before.”

I admitted that I had used my wife’s dildo before on my ass when she was out-of-town many times.

I felt lube on my ass as Mistress Tessa said, “My friend here will use the eight-inch strap-on to get your ass ready for Jerry, my gay neighbour.”

“No, Mistress, I really don’t want to be fucked by a guy,” I said in a whiny voice.

She laughed, and said, “You have no choice, sissy.”

Then, as I started to protest more Mistress Tessa forced her seven-inch strap-on in my mouth at the same time the eight-inch pushed deep in my ass.

Sometime during this pounding, I heard the door open. Mistress pulled out of my mouth and my first real cock replaced the dildo. It was so big that I was instantly gagging as he face fucked me. Then I heard a voice say, “He’s ready,” and the dildo was pulled out of my ass as the real cock left my mouth.

Mistress Tessa said, “Fuck him bareback, Jerry”.

I heard Jerry say, “There’s no way I’m fucking this fairy fag bareback.”

Tessa said, “Don’t worry. I can honestly say that you’re his first cock, and with that tiny pathetic cocklette there’s no way he’s getting any from a woman.”

I started to protest and then a pair of dirty panties was shoved in my mouth. Jerry then shoved his big cock right in my lubed and well used ass. Jerry fucked me in several positions for what seemed like an hour. My ass was so sore when he finally pulled out and sprayed his cum all over my face and in my open mouth. I heard Mistress say, “Smile,” and a camera clicked.

Then a gloved hand scooped cum off my face and fed it to me. I heard Jerry getting ready to leave as the girls thanked him and again the other girl’s voice sounded familiar. That sounds like my step-daughter Amy, I thought to myself. I dismissed the thought as I remembered she was going to college across town and should be in classes.

Just then the blindfold was ripped off and I was staring into Tessa and Amy’s faces. Amy said, “So, Dad, this is what you like to do?”

I started to say something, and she said, “Shut the fuck up and let me talk. I know Mom doesn’t fuck you except once a year on your birthday and I have a feeling she has several lovers on the side. Before today I felt bad for you, but after seeing your tiny, pathetic, clit-sized dicklette and experiencing what you like to do, I feel sorry for Mom.”

I started to say something and she slapped me across the face. She said, “I should tell Mom and get your loser ass out of our house, but Mom definitely loves having your money to spend.” Just then Tessa yanked me to my feet. Amy continued, “We want you to see the pictures we took of you.”

I saw on the big screen pictures of me sucking Jerry’s cock, getting fucked by Jerry, and eating cum filled condoms like a total depraved slut. There was also a short video of me begging to eat cum.

Amy then pointed down, and said, “How disgusting, she is getting hard seeing all the fun and look at those panties filled with cum.”

It was just then I realized that I had cum while Jerry fucked my ass. Tessa pulled off my panties and shoved them in my mouth and ordered me to lick them clean. Then, while I was sucking them clean she untied me and I stretched my aching arms.

Amy said, “Jerk your little cocklette off and cum on my strap-on and then lick it clean. Make sure not to get any on my legs or I’ll get out the paddle.”

I started to jerk off and after three strokes I shot a load on the strap-on. I looked in horror as one spurt hit her thigh. I knelt down and wiped it off her leg with my finger and licked it clean, then I sucked the rest of the cum off the strap-on while Tessa filmed me. I knew what was coming next, so I bent over the table and in ten seconds the first hit of the paddle jolted me. First Amy was swatting my ass with it so hard fifty times before she got tired and then Tessa took over.

When they finished as they surveyed their handiwork of my red ass and the tears in my eyes, Amy said, “We need to discuss the future. I see two options Dad, one is I tell Mom what a loser you are and she divorces you. Two is you agree to an extra one-thousand dollars per month allowance for me and an extra one-hundred dollars anytime we’re together for me to dominate and abuse you. Which one do you choose, Sissy?”

I answered that I would choose option two.

Amy said, “Good choice, and now an additional feature of option two is, I will be setting up from afar meetings for you to suck and fuck guys as well as eating your own cum. Any time I request this, you will be required to email me picture proof.”

I agreed and they tossed me my clothes and said get changed and get the fuck out.

The End.