My Sissy Life free porn video

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Years of emasculation and feminization by my ex-wife and her live-in lover, plus constant exercise and the female hormone drugs I take have paid off. Of course, I'm still a man, but a man with breasts, wider hips, and a rounder, more womanly butt.

I have no hair on my body at all. Oils and lotions have made my skin soft and smooth. Wigs and make-up contribute to my femininity.

I believe I'm too big at 6'5” to pass as anything other than the cock loving sissy I am. Being short-waisted, in the stiletto heels I usually wear, my long shapely legs attract plenty of male attention and I've become quite the exhibitionist.

What pulls my chain, so to speak, sexually is humiliation, degradation, domination, and rough sex by men. Lots of men! My appetite for cock is boundless. I'll drop to my knees anytime, anywhere to worship male cock and balls.

In the porn theaters and bookstores where I troll for sex, most men want their cocks sucked. I sometimes get lucky and meet a man who wants more. 

By request or on command, I'll bend my knees to lower my butt or lie down and raise my butt to give men easy access to my tight sissy fuck hole. Sometimes a man will pull me down to sit on his lap. I can take a hint. My hand will guide his hard cock to my dark cavern of earthy delight.

I'm in a relationship with a guy I met while sucking cock at a porn theater. His name is Ralph. I usually call him 'Master'. He calls me 'Slut' and sometimes 'Whore'. 

Ralph gave me a sissy name that I like a lot. I use it for my cell phone and email messages. When I meet a man who asks me my name, it gives them a good idea of what to expect from me. My sissy name is Ima Rimmer.

Ralph is not rich or handsome. His cock isn't huge. He's half a foot shorter and a few years older than I am. Even so, I'm pleased to be Ralph's submissive fuckmeat 24/7.

The night I met Ralph, I was wearing a short, tight undershirt dress I'd found in a thrift store. Thigh-highs and heels completed my costume. I had learned that when I was in drag, men would approach me in the theaters. As a submissive, I preferred men to initiate our sexual encounters, rather than me asking them.

Ralph wanted more than just a good blow job. He fondled my breasts there in the dark theater. I adore a man's strong hands on my body and urged Ralph to handle me roughly if that would excite him. He needed no more urging and dug his fingers into my soft tits and twisted and mauled them.

I was moaning and writhing in ecstasy there in the front row. That we were attracting the attention of other men seemed to turn Ralph on. Our growing audience certainly added to my pleasure. Ralph pulled my dress over my head and off when I whispered loudly. “Suck my nipples. Bite them.” 

Ralph pushed me down to kneel on the old and filthy carpeting and pulled my head to his crotch to suck his hard cock. Hard, the object of my desire was about seven inches long. The velvety, circumcised head was half again bigger around than the shaft, which sported an endearing pronounced bend to the left. 

I took the entire length into my throat and licked his golf ball-sized balls. He slid down in his seat and commanded me to "kiss my ass". I jacked his cock with one hand while I pushed my tongue as far as I could up his anus.

His cock began to jerk and I knew he was about to ejaculate. I wanted his cum in my mouth and moved my head back up just in time to feel big gobs of creamy jism shoot forcefully onto my tongue and throat. I milked his gradually shrinking cock with my lips, grateful for every drop.

Breathing hard I sat back up in the theater seat. I was almost nude and had no idea where my dress was. Ralph traded seats with a man who was reaching past him to fondle my tit and then I had a guy on each side. A hard cock in each hand.

I got back on my knees to suck and fondle those two and then one more horny male. I eagerly swallowed all their cum but the intensity I'd felt while servicing Ralph was missing. 

Closing time at the Palm Theater always comes too early. The movie screen went dark and the house lights came on. I was looking around for my dress when I felt a hand grab my ass cheek. My pulse quickened when I turned and saw it was Ralph.

He said he didn't want the night to end yet and if I would give him a ride back to San Francisco, where he lived, he knew I wanted to be fucked and he was willing to fuck me. Immediately my ass tingled with anticipation. I appreciated the way he'd propositioned me...He would be doing me the favor of fucking my horny ass.

Of course, I would drive him home. It would be my privilege and I'd be extremely grateful for a hard butt fucking. He complimented my figure and told me to forget my dress. He liked looking at my “pretty” body and planned to show me off in the city.

I felt this might be the start of a good relationship when he put his arm around my waist possessively and escorted me through the brightly lit theater lobby. On the street, the cool night air felt good on my overheated nudity. My nipples got hard and my little cock shrank to a nub.

In the parking lot, illuminated by the big floodlights and clearly visible to several men watching our exit, Ralph made me kneel. Sharp gravel dug painfully into my knees while he peed in my open mouth. I swallowed every drop of his golden elixir and knew I would do anything he wanted.

Ralph was pleased when I directed him to my nearly new van. 

“Yours?” he asked.

I said it was a work van that I had taken when I left the architectural millwork company I owned. I volunteered that I'd left the business and that I wasn't wealthy but could now afford to fulfil my erotic fantasies full time.

That piqued Ralph's interest and he wanted to know all about my fantasies. I told him what I craved was total submission and servitude to a demanding, masculine, and imaginative master. One who would dominate me day and night. I told him of my need for public humiliation and especially to be used by many men for their sexual satisfaction.

During our conversation we had climbed into the back of the van, which was so far, devoid of any creature comforts. I lay on my back on the floor and pulled Ralph on top of me. Even though he had clothes on I wanted to protect him from the cold hard steel. I have a strong masochistic streak. The discomfort I felt added to my pleasure. His hands were again fondling my breasts and he was dry humping me.

He took his weight off me and told me to roll over and spread my legs. Now I was face down. I felt bolt heads pressing into my cock, thighs, and breasts. Ralph spread my ass cheeks with both hands and I felt his hard cock pressing the entrance to my tight and unlubricated fuck hole. I pushed back and tried to stifle an involuntary shriek of pain as his cock penetrated me.

He knew he was hurting me but I urged him to fuck me hard and fast. I was crying and moaning but pushed back to meet his every stroke. He cursed me and I tightened my sphincter to increase the pleasure he took from my pain.

Ralph had already ejaculated in the theater, so he fucked me for about an hour, there in the van. When he slowed the rhythm of his assault, I urged him on, panting “Harder” and 'Don't stop, please don't stop”. With strong hands, he ground my sensitive nipples into the hard steel floor. My legs were trembling and shaking and I felt my tiny cock cumming beneath me. At last, with a shout, Ralph shot his second load into me.

We lay there, both breathing hard. Ralph's cock slowly shrank and a contraction of my ass ejected it. Underneath him, I rolled onto my back and pulled him up to clean his precious tool with my tongue and my lips. He sat on my belly and toyed with my tits and thrilled me when he agreed to make me his slave and fuckmeat.

We got out of the van and once again I squatted in the now deserted parking lot to be used as Ralph's urinal. This time I was able to press and grind my balls into the gravel. In my zone of mindless erotic submission, the pain was pleasure and Ralph knew it. He made me crawl on the gravel to the van.

He pushed me over onto my back with his foot. He stood over me and hacked up a mouthful of phlegm which he drooled into my receptive mouth. As the huge gob of slimy mucus trickled down my throat I knew I was owned.

Ralph said he hoped I could drive while he played with me when we were in the van. I hoped so too. A traffic ticket or worse, an accident would spoil one of the best nights of my life. It wasn't easy to concentrate on the road with Ralph's hands mauling and milking my breasts. He played with my tits and my thighs and told me he knew a lot of men that would appreciate my femininity and my talented ass and tongue.

Thankfully we made it to the city without incident. We were in the Tenderloin district. An especially seedy downtown part of San Francisco. Even at three in the morning, there were men on the street and a few hole-in-the-wall sandwich shops open. There was at least one dingy looking bar on every corner, all closed at this hour. Shops that advertised porn and adult novelties and little movie theaters were everywhere and a few were open.

Ralph told me I couldn't come into the hotel. No women, gays, or visitors were allowed. He would move to an apartment and pay the rent by whoring me out. Until we had our apartment, I would park the van in the alley behind his hotel. The van doors would only be locked if I was with a man who wanted privacy.

Ralph told me the word 'no' was no longer in my vocabulary if I wanted to be his sissy. I would never say no to him or any other man. If a man wanted sex with me I would ask Ralph's permission but if Ralph wasn't available, I would willingly provide any service demanded.

Looking at a gnarly old wino staggering along the sidewalk I pointed to him and asked Ralph if that rule included any filthy old bum who noticed me. Of course, the answer was yes. 

If I wanted any clothes, other than the heels and thigh-highs I had on, or a blanket or mattress to make the van more comfortable, I would have to earn the money to pay for them. Ralph said we could go shopping the next day if I turned some tricks that night.

I told him I'd like to do that. It wouldn't be the first time I'd been used as a whore. The thought of displaying myself on the street for any man to use was both frightening and exciting. Even though I was exhausted from my cocksucking in the theater and then Ralph's hard fucking, I perked right up.

Ralph directed me to his hotel. Before he got out I asked him how much I should charge. I was his whore and any money I made would be his to spend, setting a price was his chore. He liked that and told me to collect $5 for my worthless ass that night.

He thought for a few minutes and added I had to guarantee satisfaction. No cum meant no charge. After a little more thought, he told me to offer a senior discount. Many old men living in the Tenderloin had a very small fixed income. 

He told me again if I needed to sleep, to park in the alley behind the hotel and reminded me to leave the van doors open. He told me to expect company in the morning. After I serviced his and his friend's “morning wood” we would get breakfast and go shopping...Assuming I had made any money for him.

Ralph went into his hotel, leaving me naked and alone in the van. 

To be continued

 

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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

2 years ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

2 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

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