Sissy Meets Her New Daddy Ch. 1 free porn video

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So I took the plunge and put out an ad on Craig’s List. I was travelling in a city about 120 miles from home and figured this was far enough to not be found and close enough to go back if I had success meeting a fuck buddy that could be longer term. I got myself all primped and wore a tight print dress, matching bra panty set subtle yet slutty makeup and my fave long blonde wig.

The ad attracted immediate attention and I was sure to mention I was a sissy who wanted to be treated like a girl. I was NOT into topping a guy…no. So I finally chose this guy Rich, who happened to be black, because he seemed so polite and chivalrous. We agreed he’d come to the hotel in 30 minutes which gave me time to calm my nerves and give myself a ‘once over’. He knocked on the door and I felt a chill but answered it quickly. When he stepped in I was surprised at how much bigger than I he was. At least 6’4 and a solid/muscular 225 lbs. If not for the tiny bit of grey, I’d have thought he played for a college football team. After I poured us each a drink we sat on the sofa and made some small talk, He confessed he had never been with a sissy before but loved the idea of a man willing to degrade himself so low that he’d wear panties and a bra just to get some cock. To be such a faggot that he would dress like a girl to get fucked. I tingled at the thought of what the night would bring me and felt myself blushing a little. I was a little embarrassed that he could tell I was exactly what he thought I might be – a sissy slut. He put his hand between my legs and reached over and kissed me on the neck. I let out a little moan and felt my little thing start to twitch. I did not want to get an erection but it seemed he was going to insist as he rubbed between my legs. I had to stand up to get it to stop, more than a little ashamed of myself.

He asked, very politely, if he could watch me masturbate while he played with himself in front of me. He said this way, my tiny nub would be out of the way for the remainder of the night. Made sense I think so I took it out and started to play with it. He took off his shirt and pants and began to stroke himself. Seeing this got me excited and I started to get into it. He told me to close my eyes and think about his dick. He began to walk towards me and I could feel it rubbing against my cheek. Rich told me to talk to him and tell him what I wanted and that I am a faggy sissy who loves cock. He had me begging him to take advantage of me while he rubbed his huge semi-hard cock all over my face. I finally came and he told me to eat it all up like a good girl. Of course I did.

I came out of my trance and realized he taped the entire session with his iPhone. I asked what was up and he just laughed and said ‘insurance’. I was told to tuck and pretty myself up in the bathroom and to get back out quickly. When I did, he told me his plans – they weren’t good.

Rich decided he needed a regular sissy to do what his girl wouldn’t. He told me he planned to make an edited version of the film to show me begging for his cock while he rubbed it all over my face then eating my own cum with his cock rested up against my cheek. He didn’t say it but I knew he had my face in the video and anyone who knew me would clearly KNOW me through the makeup. I was fucked.
Rich said ‘come here pussy, it’s time to care of your new owner. Let’s see how good of a cocksucker you are. I reluctantly went down on him and started to lick and suck his cock. He was delicious but I was now scared of what was to come. He put his hands on my head and guided it up and down almost gagging me. I’ve practiced for so long on a dildo I didn’t choke but it was hard to keep the rhythm. I asked him to warn me when he was going to cum and he laughed. Turns out his warning was a tight grip over the top of my head while he drove it deep into my throat and spurted gob after gob of cum into me. Of course, this was all on video too. Relieved it was finally over, I figured I was done being used. Wrong.

Rich told me to get him another drink and come sit next to him. He told me to kiss and lick his nipples while he laid out my future. I was now his. He knew my name by running my plate through a friend and confirming it with the front desk. Everyone I know will get a copy if I don’t comply. I explained I lived far away and he calmly replied ‘so what the fuck do I care? You will drive up here whenever I say and stay as long as I want. I OWN you sissy.’ Yup, I was fucked. He laughed and said it was too easy. He had me begging to suck his cock while I jerked off then he had me ACTUALLY sucking his cock and swallowing it – all while dressed like a slut in dress, wig, makeup. I could see him start to get hard again, no doubt from my playing with his nipples. He told me he needed one more video to seal the deal. He wanted one of me fucking myself with his cock. He told me what he expected to say in the video and warned me not to fuck it up. I promised I would do as instructed so he patted my head and said ‘good sissy’. Get to work.

He laid back on the bed and started filming. I walked up, as sexy as I knew how, and asked ‘Daddy Sir, may I use you cock to fuck myself? I’m so horny and I really need to get off on your cock.’ “Sure” he replied. So I pulled up my dress a little, pulled aside my pantied and lubed my pussy. I climbed on top of him, facing him, and worked his magnificent dick into my ass and slid down on it. It hurt but I’ve had quite a few things up there so I adjusted quickly. I did as previously instructed and rolled on him and really worked it in and out of my pussy. Funny thing is, I really enjoyed this although it was extremely humiliating. “use my cock you sissy faggot, you like my cock, faggot?” “Yes Sir, your cock is awesome, thank you so much for this Daddy.” I worked harder and harder and felt a weird feeling in my inner groin. I kept grinding and the feeling started to overwhelm me.

Grinding on his cock I buried it to the hilt and felt waves of pleasure flood through my groin…..unbelievable. My little nub dribbled out some goo but was still pretty much soft in my panties. I fell forward and kissed him instinctively and he tongued my mouth while still buried inside me. I found myself begging him to fuck me and he did. Hard, long strokes. He rolled me over on my back and got between my legs .I raised up my knees and brought them back so he could settle in between my legs and have proper access to my hole. Rich leaned forward and our chests met. He nuzzled his face in the nape of my neck and went to work. I had both hands on his ass pulling him into me. ‘please fuck me daddy, I need your cum.
Holy Shit! Did I just say that. ‘Don’t worry sissy’ you’ll get every drop’ he said. Uh-oh.
He pumped then put his lips on mine, I held his ass tightly and he gave a single deep final thrust filling me with cock. I felt him empty his bowels into me and could feel it already leaking out. He pumped slowly forcing all of it deep into me as if we were trying to get pregnant. I was whimpering and could only thank him and meet his kisses. I truly felt like Rich’s girl.

When he finally pulled out he said ‘you gotta clean it off now. If you’re going to be my regular thing, I need to leave here clean. And you ARE going to be my regular’. I trembled and went to work. “so let’s set up some ground rules Jim.’ Shit he really did know my name. I kind of snapped to attention/reality. “your name is jamie now. And you WILL come to me when I want where I want. And I WANT you back here Tuesday next week. This hotel and be dressed to go out to dinner.’ Oh shit, ‘but I am not passable’ I pleaded. Riche snickered, ‘I don’t give a shit, you’re going out next week. It will be hysterical seeing you humiliated in public like a little faggot trying to get laid. And in case you get any ideas, I’ll be emailing you a copy of your performance. Bye sissy, see you next week.’

I’m fucked.

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Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 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...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven 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 Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - 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...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sissy gets a black master

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

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm 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 Doctor Shirley Williams. 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 Peregrine's...

2 years ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen 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...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

2 years ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

3 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl 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, fictional fantasy work. No references...

2 years ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

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