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It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends.

Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serve them, naked except for my collar and tiny steel chastity cage. They all had great fun teasing examining my locked little peepee. As the evenings went on they'd take turns fucking my ass with strapon cocks and dildos, milking the cum from my swollen balls. I'd thank them by bringing each of them to orgasm with my mouth.

One night, as she was fucking my ass in the bitch position on a table, one of the ladies suggested that it was time for me to take the real thing. A discussion ensued, one in which was had no say. It seemed that this lady had a friend, black with a huge cock, bigger than any of the strapons or dildos I'd taken, and that he loved fucking the manhood completely out of little white boys like me. As the discussion went on I was filled with a mixture of excitement and fear. My caged little peepee was leaking cum on my belly. It was agreed that she'd call him and a date would be set for my deflowering party.

A couple of days later I was informed that the party would be the coming Friday night. All week long I was on edge wondering about my fate.

Friday eventually came around. Mistress gave me a bottle of Nair and a razor that afternoon telling me to remove all of my body hair and shave perfectly smooth. Half an hour later I was done. Just before guests began arriving she sprayed my lightly with some flowery perfume and applied just a hint of makeup to my face. She then had me put on some 4 inch heels and a silver anklet and practice walking in them, which to both our surprise I took to quite well. I quickly learned that it was easier if I adopted a more femine gait.

I greeted each of the guests at the door, naked except for my collar, cage and heels. The guests were mostly female, a few with boys in tow. Once inside the boys had to undress, house rules. I was pleased to see that all seemed so excited about the evenings events. At about 9 Eric arrived.

Accompanying him were two white boys, completely feminized in makeup, hairstyle and slutty clothing. Once inside the two white boys also removed their clothing revealing the tiniest shrunken little dicklettes I'd ever seen in person. And both had the beginning of boobies growing, with puffy nipples. As they turned around I notices that both wore butt plugs. I wondered if that was to be my fate.

Eric is a monster of a man. Well over 6 foot tall probably 250 lbs, muscular with a huge bulge in his khakis. He was very pleasant as he introduced himself, reaching down to give my little peepee a squeezes with his huge hands. He gently patted my ass saying we'd get to know each other better.

This evening I didn't have to serve refreshments. The other boys there took care of that task. That freed me to spend more time with rhe guests, all who delighted in telling me how the looked forward to seeing my tight white ass fucked. Many examined my locked little peepee and had me bend over so they could get a before view of my ass. It was all so enjoyable for them and humiliating for them. Likewise many of the ladiea were feeling up Eric to see what he'd be working with.

About 11:00 pm Mistress announced that it was time for the main event. A padded table was brought out to the middle of the living room. I was told to lay on it on my back and my hands were secured at my side, a pillow under my head so I could see all that was gpoing on. Eric's boi's removed his clothing revealing a chiseled body and a cock like a log. Still not fully hard it was about a foot long and as thick as my arm. The audience gasped. Both sissy's dropped to their knees and began stroking, licking and sucking on that massive cock and set of balls. It was obvious to all that they worshiped it.

Soon it was rock hard and pointing forward. Eric pushed his sissy's away and moved around so everyone could see his huge black cock. I was trembling, mostly due to fear when one of the ladies called for a measurement for the record. Another pulled out a cloth measuring tape and stepped forward. She pronounced the results, 14 inches long and 9 inches around om the shaft. The swollen head was even larger. As the room erupted in gasps and cheers I was nearly overcome with trepidation. Mistress could tell and soothed me by whispering in my ear that Eric's little pussybois take that cock regularly. If they could handle it certainly I could.

Two ladies grabbed an ankle each lifting them into the air and exposing my butthole. Another started preparing me by lubing me up with a large quantity of lube. First one finger, soon two, three and four. She pronounced me ready and retook her position in the circle surrounding us.

Eric approached stroking his monster cock before him. My ass was lined up perfectly. He smiled and told me and everyone there that I would be experiencing bliss like never before and that I'd never be the same. I had no doubt. "Ready sissy?" he asked. I meekly nodded accepting the inevitable.

That huge cockhead felt hot as it rested at my entrance. I concentrated on my breathing as he gently pushed forward stretching my ass like never before. I screamed in pain until his big cockhead was fully inside and he stopped to allow me to adjust. I could barely hear the small talk about how much he enjoyed breaking in little white boys and turning them into faggots for black cock.

My breathing returned and I adjusted to the stretching I was receiving. Eric soon started pushing deeper, thrusting back and forth, a little deeper with each thrust. Each thrust resulted in pain and I could feel my insides being rearranged. Soon he announced he was halfway home. Deeper he penetrated me. I could focus on nothing other than than the sensations I was receiving from the huge cock fucking me deeper with each stroke. Everything else was a blur.

After what seemed an eternity I felt Eric's balls and body press against my ass and thighs. He was all the way in! I'd never felt so full and twisted up inside in my life. I could hear the cheers from the audience.

Then the real fucking began. Eric fucked me in long strokes, slowly at first picking up the pace. Before long the sensations turned to a more pleasurable. The pressure and stroking of my prostate caused my little peepee to leak cum all over my belly, eliciting laughter from the audience. After only a few minutes Eric was fucking me long and hard, showing no mercy. He slapped my ass and asked if I was a faggot sissy bitch. As the pleasure built inside me I screamed out "Yes! I'm a faggot sissy bitch. Fuck me with that big cock please!"

Then it happened. I felt a wave of pleasure start deep inside of me and quickly envelope my body. I started shaking and my muscles tightened. My little peepee spewed a stream of cum all over my face and chest. My first sissygasm! I'd never felt anything like that before in my life.

Eric kept fucking me right through my sissygasm.I had no clue what he or anyone else was saying. I was sweating profusely and trembling. My eyes must have rolled back in my head as everything went black. I could feel Eric's mighty cock swell and his thrusts become more rapid. Then He thrust balls deep and I was filled with hot fluid squirting deep into me. The sensation, and the mental thoughts accompanying it, caused another incredible sissygasm. I bounced around, screaming in pleasure. Again my little peepee squirted. For several minutes afterward I spasmed in pleasure as Eric stayed inside me.

Eventually he pulled out. Cum was all over the place, pouring out my gaped and sore ass. As if on cue Eric's sissybois knealt, one cleaning his softening cock, the other licking up all the cum coming out my ass. Mistress scooped up my own cum off my belly and fed it to me. Eric, admiring his work, pronounced "And that ladies is how you turn a little white boy into a faggot sissyboi for black cock." I had to agree.

I could barely stand when untied. My legs were shaky and my ass sore. And I was dehydrated. As I drank a bottle of water everyone congratulated me on my performance. Apparently it was entertaining.

My eyes kept being drawn to Eric's big cock. He was sitting on the couch naked, his cock resting on his left thigh. Both his bois were sitting on the floor at his feet, their tiny dicklettes semi hard. Eric caught my eye and told me to come over and have a seat on his lap. Following instructions I sat on his right thigh putting my arm around him for support. His huge soft cock was mesmirizing. My mind was still entranced by the pleasure it had brought me just minutes before. He told me to stroke it with my right hand. My hand couldn't wrap around it completely. Soon I felt it getting hard in my hand. I noticed both of his sissy boys squirming and licking their lips. Obviously they were addicted.

"Make it real hard so you can ride it" Eric told me. I squeezed and stroked his big tool until it was at it's 14 inch length again. I could feel the heat building inside me, wanting to feel it inside me again. Somebody squirted some lube on that cock as I stroked it to full hardness.

I placed one shin in each of his powerful thighs and elevated myself. Holding onto that massive rod I impaled myself on it, taking almost all of it in one stroke. I could see everyone watching as I bounced up and down until I was taking it all. What a glorious feeling. Eric grabbed me with two hand on my waist and helped me speed up the pace. Up and down I rode.

My legs weakened and I placed my hands on his shoulders for support. Soon I felt a stirring inside again and knew I was going to cum. All at once it hit me. I started trembling and my orgasm burst forth. Screaming in pleasure I collapsed with that massive cock inside me, head on his shoulder, arms wrapped around him.

Eric stood. One hand on each of my ass cheeks helifter me easily up and down. I was completely powerless, just his fuck toy at this point.

Eventually he took me over to the table. Laying me face down with mt legs hanging over he fucked me from behind. His stamina was amazing as he power fucked me pulling that massive cock head out with each stroke. He smacked my ass and pulled my hair. I offered no resistance. Again and again my body writhed in orgasm. By the time he filled me with cum again I had no idea where or who I was. The flooding of my insides was too much and I passed out.

At about 3 am I awoke on the floor in the fetal position. Everyone was gone and I was covered with a blanket. I crawled to the bathroom on as my legs were like jelly and my ass was so sore. Afterwards I returned to my spot on the floor and slept until noon. When I awoke I took a shower and examined my sore ass. It was swollen and puffy, and tender. I couldn't walk right for three days and sitting was rough. But I knew without a shadow of doubt that my locked up little peepee was of no consequence to me. Sexual pleasure for me henceforth would have to be obtained by being fucked by big dicked black men.

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I had worked at Stonecliffe School for 3 years as an assistant caretaker. My boss was an old guy who had worked there forever. He was nearing retirement and I was due to replace him soon and I was very happy about this. I had always enjoyed the job even though the pay was lousy, partly because there was never much to do. But mainly because Stonecliffe was a Private All Girls School! And it was stuck out in the country which meant all the students and all the staff lived on the grounds in...

1 year ago
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Sex With the Wife Of Caretaker of Guest House Free Sex Stories and Adult Erotica Stories

My name is Aryan and I was posted in Chickmanglur, an area with a lot of hills and coffee plantations. I was sent there for handling the production work. I was given a guesthouse to stay and a house-help, a man named Hari, who helped me with basic things I needed. His wife used to prepare food and do cleaning stuff for me. His wife, Rekha, was a very beautiful and desirable woman. I am going to share my story of how I came closer to her and had sex with the wife of caretaker of my guest house....

Maid/Servant
2 years ago
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Chinese TakeoutFor Breakfast

Jason quietly put his key in the lock. It didn’t seem to be going in, he panicked for a minute thinking Marcela had changed the locks in her anger, but when he realized it was his hand shaking, he chastised himself for being so paranoid. He steadied himself, taking a deep breath and then slipping the key into the hole, letting out his breath as the door soundlessly swished open allowing him to walk into their apartment. He looked around the corners, trying to assess where she actually was,...

3 years ago
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Sleight of Hand5 Caretakers

Days in Hades and nights in Paradise stretched on for months. I was working at physical therapy six or more hours a day. I was working in the store four hours a day where I practiced sleight of hand. I graduated from wheelchair to walker to crutches. Lisa worked right alongside me. Every exercise I did, she did twice. She was determined that she would be as fit as was required for an excursion on Chaos. When I was working at Shannara, Lisa took instruction in self-defense and Tai Chi. Not to...

4 years ago
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Picture Taker

Picture Taker I went looking for my camera and it was missing. When I asked Mom about it, she said that my sister had borrowed it, and that she had given her permission to do so. I had taken some nude pictures of myself beating off and they were still in the camera. My hard cock was in my hand with a lot of stroking and some pretty amazing squirting. I had to get that camera back. Mom said that they were out taking pictures somewhere in the woods in a clearing near a stream. I...

3 years ago
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Guest House Care Taker Took Care Of Every Need Of The Guest

Hi ISS readers, it’s been a while I shared my last experience. So here I am with a new story. So this  actually happened in Mumbai where I was for an official trip. I am 26 year old living in Delhi. I was in Mumbai for a project and I was required to be there for 2 weeks. The client has set me up in their guest house which was situated in Dadar. Guest house was simple, 4 rooms on the 4th floor of that building. There was a care taker named Vishnu, he was from Nepal and a cook name Preeti, she...

1 year ago
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Stake

What’s at Stake over at Stake.com? It’s a little different from the type of joints I typically review here at ThePornDude because usually, the wager is just on how hard you’re eventually going to cum into your old trusty, crusty gym sock. Here, you can bet and win real money instead of just hoping your orgasms are good. Some folks even say that gambling is just as much fun as masturbation and a lot nicer than fucking your fat wife, but it doesn’t take a genius to notice that not all online...

Betting Sites
3 years ago
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Train Full of Cocks

I stared at my exposed tit, and felt a rush of nerves get me.As I contemplated making a run for the exit, the guys around me circled around what little space we had in the train.I grabbed the broken piece of my red dress and pulled it back up trying to cover up my right tit, but the guy sitting next to me was keeping me by playing with my nipple."Um...listen..." I said as I looked for words to say to him with a devilish grin on my face."Will, My name is Will, sweet sexy foxy baby," he said to...

2 years ago
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Trained My Girlfriend To Be A Slut Now Enjoying Every Moment Of It

This is my first story, it will be bit long but it will be worth each second of yours so I won’t waste your time and will get down to details.My name is Akshat (24 yrs., 5.9 ft.) and my girlfriend name is Priyanka (21, 5.4 ft.). She is one hot girl every guy dreams to fuck. I know everyone in their story write the same thing but believe me if you see her in real, your animal behavior will go out of control and you will just want to shove your cock in each of her hole all day long. She has a...

3 years ago
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Lost Art of CockSucking

So if the title of this article makes you gasp, you now know why. I use the word cocksucking because it is what it is. It is not a blowjob; I am not blowing on it. It is not fellatio or giving head. I am sucking on a cock, and I have little shame in using such jargon. Besides, the very word, cocksucking, is an aggressive word, it sounds more sinister, more forceful. There is no weight to the other words.Cocksucking is a lost art, and in an age where sex is deemed as something impersonal,...

2 years ago
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Constrained in Corsetry

CONSTRAINED IN CORSETRY Although I am not into serious bondage I love the erotic pleasures of wearing corsetry and other tight feminine garments next to my skin. When wearing suspenders and stockings I love the erotic sensation from the tightness of the top of my stockings gripping my thighs and the suspenders brushing against my thighs as I walk, as I envisage my suspender belt and stockings framing my clit and balls. I also find the tightness of bras and corsetry such as a girdle or...

1 year ago
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LORRAINE AND COCKY

Lorraine works at the library, my home away from home. Over time, we’ve learned each other’s names, say hi upon greeting, and sometimes chitchat when things are slow. She’s older than I am and sometimes dresses a bit frumpy, but just when I’ve forgotten about them, she’ll wear a long, clingy t-shirt under a sweater that makes clear how big her boobs are. I love that about her. That and her way with subtle innuendos that keep me guessing whether I’m mistaking something innocent or being...

2 years ago
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Slow On The Uptake Ch 01

‘What the hell is wrong with you?’ Blake could not believe what he was hearing from his best friend. ‘Nothing, I just think that maybe he deserves a second chance.’ ‘A second chance? Really? I thought you already gave him that along with chances three, four, and five. ‘ Blake could not understand how she was even thinking about staying with her boyfriend Dev, all they did was fight and have sex. Dev never wanted her to do anything but sit around and wait for him, but he just went and did...

3 years ago
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Dont Sleep on the Subway Book ThreeChapter 34 Jan 1943 British Retake Tripoli

“I have in this War a burning private grudge—which would probably make me a better soldier at 49 than I was at 22: against that ruddy little ignoramus Adolf Hitler (for the odd thing about demonic inspiration and impetus is that it in no way enhances the purely intellectual stature: it chiefly affects the mere will). Ruining, perverting, misapplying, and making for ever accursed, that noble northern spirit, a supreme contribution to Europe, which I have ever loved, and tried to present in its...

3 years ago
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Fucked Kakinada Office Caretaker

Hello Friends   This is Sarma,38, currently based in Hyderabad. This incident that I am about to recount happened some five years ago. At that time I used to live in New York with business interests in Kakinada. I used to travel to India every few months, usually short arduous and busy trips.   In January 2011 I came to Kakinada and straightaway dived into our business with my local partner. Business was expanding and my partner just set up a new office on the top floor of a three-floor new...

4 years ago
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Caretaker Cum Maid For The Hostel

Hi friends, I’m Ted. I am living in Kerala. Please forgive for any mistakes. Also, do send Feedbacks on All types of feedbacks are welcomed. CARETAKER CUM MAID FOR THE HOSTEL The heroine of this story was our caretaker cum maid. She lived adjacent to our hostel. Since the owner of our hostel lived abroad, he made her in charge of the hostel. She used to collect our rents and took care of the hostel. She also used to clean the hostel. Speaking about her, she was about 45-50 years old. I didn’t...

3 years ago
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Our horny caretaker

Hi am Nicks a guy of 26 who was working abroad and right now back in Bangalore heading a pvt. Ltd. Co. This is a real incident which happened to me a couple of months back. I stay in a PG Accommodation and my room comprises of one bedroom, drawing/dining, attached bath and balcony. Our caretaker is a lady of 36 who is a widow. When in got accommodated soon after I returned and joined with my new firm in Bangalore this lady was serious and she used to talk to me less compared to other occupants...

1 year ago
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Trained by a Shemale Mistress Part 2

Several weeks passed. I was thinking about Ashleigh almost constantly. I did not know it at the time, but she would be the transexual that would change my life forever. Some ways quite positively, and in at least one a whole lot negatively, but more of that later.Our second encounter was in NJ. I was on a business trip when I saw Ashleigh was in NJ, near Philly. I made my appointment for that very day, but arrived about 15 minutes late. Ashleigh was sitting on the couch in her room. she looked...

2 years ago
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Trained by a Shemale Mistress Part 1

I did not know it at the time. I thought I was just sleeping around with shemales that I found attractive on Eros, Backpage, and other sites. What I was looking for, subconsciously was a 100% top dominant mistress. In retrospect when I saw the first shemales of this journey I was turned on by their control, but immediately turned off when they submitted to my cock, either sucking it or taking it in the ass.Not until I met Ashleigh did I realize that I wanted to be dominated, not hurt or...

1 year ago
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Trained by The Tranny

I have always been considered a strong athletic straight black man. I have fucked a plenty of women being an executive in a high profile position. I had everything a man could ask for Power, Property and Plenty of Pussy. Well in life, all things change. I had just landed another two million dollar client and was out celebrating with friends over a local bar. I was feeling real good and I never believed in going home alone…..so why should tonight be different. Then after a few or too many drinks...

She Males
2 years ago
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High Stakes

HIGH STAKES By Ken Meredith John Groom had it all. He was 35 years old, rich, single, and handsome. He owned numerous mansions, cars, boats, toys, and even a private plane. John groom had made his fortune by working 14-hour days, seven days a week. When he had graduated from MIT at the top of his class, Groom received many offers from the top technological firms in the country. He turned them all down, because he knew the real money was in owning his own firm. He created one of the...

2 years ago
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High Stakes Golf

Tuesday Night It was a Tuesday night and I had worked late and didn't get home till 7:30 that evening. When I walked in the door my wife Lori told me that Ben called three times. She said, "He said he needs to talk to you tonight. I asked, "Did he say what he needs to talk to me about?" Lori said, "No. I asked he if he wanted to leave a message and he said he would call you later" I said, "Well it must be important if he called three times. I better call him before dinner." I went...

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