A Visit To A Mistress

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 2 weeks before my business trip took me to where she lived. She told me it would be $250 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 coworker 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 I looked like."

"Please don't tell my boss," I said. "I'll do anything you say." Quickly I stripped and stood before her naked.

She looked at me and laughed. "Well you are ugly, and your shriveled up cock is so tiny. I can't believe your wife ever fucks you."

I admitted that she didn't. "Because it takes longer to clean up than our fucking lasts."

She laughed again. "Well, ok. You can call me Mistress or Mistress Tessa." She tossed me a pair of aqua colored panties. "Put these on so I don't have to see that disgusting penis."

I stepped into the panties as she went over and sat on the couch.

"Crawl over her you sissy slut," she ordered, and 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 5" heel all the way in as she laughed and took pictures with her phone.

"Lick the 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, you 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. "Yes, Mistress." I heard her rummaging around in the next room, and then I could hear her footsteps as she reentered the room I was in. All was silent for a moment, and then I heard a swoosh and a smack as 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 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 7" strapon 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." I eagerly sucked it and could only down about 5". 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 10 minutes of this she pulled out of my mouth, put a condom on the strapon 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 cock and jerk yourself off into it." I did as instructed and I came on the second stroke and she laughed saying "Wow, you are a quick one."

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 is too much for me."

Abruptly she pulled out of my ass. "Flip over on your back." I did and she grabbed the bowl with her gloved hand and. "Open wide." As her knee was 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 the 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 $500, I have some fun planned for you.

The week went by so slowly and I was on edge every day. Friday at 5:00pm 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 then said, "Sissy fag, we have a treat for you. My friend here brought 2 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. I opened wide as each condom was poured in 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 strapon 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 my 8" strapon on you to get you ready for Jerry, my gay neighbor."

"No, Mistress, I really don't want to be fucked by a guy!"

She laughed and said, "You have no choice, sissy." Then as I started to protest more Mistress Tessa forced her 7" strapon in my mouth at the same time the 8" 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 was replaced her dildo. It was so big that I was instantly gagging as he face fucked me. Then I heard a voice which said, "He's ready," and the dildo was pulled out of my ass and the cock left my mouth.

Mistress Tessa said, "Fuck him bareback, Jerry".

I heard Jerry say, "There is no way I fucking this fairy fag bareback."

Tessa said, "Don't worry, I can honestly say that you are his first cock and there is no way with that tiny cock he is getting any from any woman."

I started to protest and then a pair of panties were showed 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 smile and I heard a camera click and then a gloved hand scooped up the cum on 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. I thought to myself that sound like my step-daughter Amy and then I dismissed it until I remembered that she was going to college nearby.

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 and now after seeing your tiny cock 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 up and 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 the cum filled condoms. There was also a short video of me begging for the 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 was fucking 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 that little cock off and cum on my strapon and then lick it clean. Make sure not to get any on my legs or we will get out the paddle. " I started to jerk off and 2 strokes in I came on the strapon. 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 strapon while Tessa filmed me. I knew what was coming next so I bent over the table and in 10 seconds the first hit of the paddle jolted me. First Amy was swatting my ass with it so hard for 50 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, or two, you agree to an extra $1000 per month allowance for me and an extra $100 anytime we are 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 with you to suck and fuck guys as well as eating your own cum. Anytime 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.