Lost Sissy Virginity free porn video

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A few months ago I truly became a sissy. I was out of town on business and decided that was the night to be who I was meant to be. I invited a man over and I'll admit it was a bit awkward, but cooler heads prevailed! He pushed me to my knees and shoved his dick in my mouth! He didn't have too much stamina though and he blew in about two minutes. It was fun but a bit of a let down.

Don't worry though, my ass was still wet and my urges were still strong! After a little bit of searching a found another man to come over. When showed up it was clear from the start who was the real man and who was the sissy bitch. Within mere moments he had me on my knees and unzipping his pants. His dick was at least 7'' and had a nice thickness to it. We started off slow. I licked his length and took his balls in my mouth. He was clearly enjoying it. Enjoying it so much that after sensual sucking his dick for three minutes he began to force me down on him more. After about thirty seconds of this I stopped resisting. I let him violate my entire throat. This severe mouth fuck proceeded for about five minutes. On about three occasions I had force myself off of him. He gave about three seconds each time to spit on his dick or my chest and get a deep breath. After those three seconds he would go right back to plowing my slutty throat away.

When he finally let my throat rest he told me to get on the bed; ass up, face down. We had merely mentioned plowing my virgin ass, but never had agreed upon it. While that ran through my mind, my body took over and I threw myself face first into the mattress. I looked to my left and saw him grabbing a condom and some lube. He lubed up his fingers and simultaneously shoved two of his fingers in my ass and his dick into my mouth. He loosened me up with his fingers as he continued to make me gag on his seven inch dick for the next five minutes.

Once he felt happy with his preparation he positioned himself behind me. Without asking if I was ready he slowed shoved his length into me. After only a couple dozen or so seconds he had bottomed out in my ass. He started to speed up and after about five minutes he had fully taken control. He was railing my now formerly virgin asshole and shoving my face into the mattress. It was at this moment he said, "Do you like that faggot?" Without even a thought of hesitation I said, "Yes, fuck my sissy ass. Spank me daddy." Not only did he spank my ass, he punished me. He showed me I was the sissy and he was the man here. He continued to ram me for another five to ten minutes and that's when he told me to beg for it. "Beg for my cum," he said. No he didn't say it, he demanded it. I was now at a soft scream asking him, begging him, "CUM IN MY ASS." I begged for what felt like forever. He obliged after not too long. He filled the condom to the brim and ended my beginning steps to sissification.

He moved off to the shore and I continued to finger my asshole on the bed until I heard the shower turn off. Honestly I should have went in with him and sucked his dick again but I was just in such bliss. I saw him off after the shower and then spent about five minutes dripping pre-cum and my sissy seed on to my own face.

It was easily one of the best nights of my life. I'd love to explore more of my kinks like being sissified while getting in the ass, being commanded by a mistress (while with a master or not), being gangbanged/bukkake, experiencing bondage in various situations, and many more! Hope you liked my story. Reach out and talk with me if you have questions!

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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...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

2 years ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

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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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

2 years ago
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Cuckold Sissys First Meet Fantasy

This fantasy summary was sent to my wife and her prospective boyfriend to let her boyfriend know our fantasies and for me to know which bits got my wife and bf really wet? And feeling very horny? Which bits she really liked? And what they would you like to add to also?The text was sent to the prospective boyfriend's iphone with a picture of me on all fours showing my girlie soft pathetic knickered and caged boi-clit after he sent me a picky of his gorgeous cock which I had previously been lucky...

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