I Miss My Sissy Football Player free porn video

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This is from a couple years back. When Craigslist still had personals.

I had an ad on CL. Looking for a sissy to suck my cock on a regular basis. I met several ... interesting girls ... on that site. In talking with one girl in particular we naturally hit it off. She loved sucking and pleasing boys. She had never been with a man. She was 19 and starting college. She was renting a room on the other side of town. After learning a bit more about her, I learned that she was on the football team, was very curious about being with a Daddy type like me, and she had never had a regular cock to suck. She was sweet and very submissive. Funny thing is ... she was taller than me and possibly stronger or as strong as me. But she is submissive and the boys she was with previously had a very difficult time being with someone who may possibly be physically stronger.
Submission is 99% mental and 1% physical. Too many Dominants do NOT understand this. I do understand. Many submissive girls are afraid to allow themselves to truly submit ... to truly allow a man to take what already belongs to him. When a sweet submissive sissy allows a man to take over, she is able to experience bliss. That bliss will be addicting. Bliss is deeper than pleasure ... deeper and stronger than happiness ... it is a state that is rarely experienced ... to be enjoyed and cared for ... not just accepted ... but cared for ... for who you are ... a true sissy. A true sissy who is only fulfilled when you are pleasing your Daddy/Dominant/Owner.
So getting back to the football player. We will call her ... Tanya. After talking a bit and exchanging many emails, I decided it was time to meet. She was going to wait for me in her room. All of her roommates were gone and she would be dressed and ready in her room.
It was mid-morning and the house was in a quiet neighborhood. I pulled into the driveway and texted her to let her know I was there. She left the front door unlocked. I walked into the house, shut then locked the door behind me. I walked around the house a bit to see if anyone was home. I needed to scout the place out a bit myself. I walked down to the basement and there was nobody home. I walked back upstairs then headed to the second floor where Tanya's bedroom was. After comfortably verifying that Tanya and I were the only ones in the house, I walked into her bedroom. She had on nice stockings, panties, bra, and she was dressed properly. Full makeup, bright red lipstick. I walked over to her as she lay on the bed. I sat down, then touched her leg. I could feel her muscles tense up a little and she said, in a shaky voice, "Hello". I said softly, "Hey sweetie ... I am here ... and I am not in a hurry". I put my hand on her chest and could feel her heart beating fast and hard. She looked into my eyes and I leaned in to kiss her cheek. I let her know that she had nothing to be afraid of. I let her know that Daddy was going to help her discover her deepest pleasures. Her voice still shaking a little, she let me know that she had never been with anyone my age. I was twice her age. She wanted to hurry up and pull my pants down to suck me off. I calmed her down and let her know I would be taking my time with her today. She was a little surprised to hear that. She seemed to calm down a bit when I told her I liked what I saw. She was ashamed of her muscles, and how she developed her body to look like a man. She said she wished she was a real woman.
I looked at her and in a firm voice told her that I know who she is. I told her she is a beautiful girl, a beautiful young woman, and is growing into a beautiful woman. She blushed as I made her look me in the eyes. I enjoyed her deep eyes, her deep green eyes. I gave her a kiss on the lips then stood up to remove my clothes. I sat back on the bed and made her get up. I had her put on her heels and walk around the bedroom for me. I made her walk toward me, then away. I had her stand next to me as I touched her body. She was getting excited. She apologized. After I decided she had done a good job of showing me her body, I had her sit on the edge of the bed as I stood up. My rock hard cock in front of her she put me in her mouth. She wanted to suck me hard and fast and she attempted to make me cum quickly. I slowed her down. I wanted her to take her time, licking, sucking, and licking my balls.
She was touching herself and that is when I decided to lay on the bed and have her suck on me. She was touching herself intensely. She said she had never sucked on a cock for this long without drinking cum. I let her know that I have a little more control than the boys she was previously with. She asked if she could cum. I firmly told her that she was not allowed to cum until she drank my seed. She asked me when I was going to give her my seed. After quite some time, I released inside of her mouth. My cock pulsating hard inside of her mouth. She tried to drink in every drop, but could not. Her eyes watered and she swallowed my seed then cleaned my cock, licking every drop off my cock and balls. I enjoyed looking at her clean me with some of my seed on her face. I let her know she could clean up a little and then she could cum herself.
I lay in the bed waiting for her to come back out of the bathroom. She walked out and was a little surprised that I was not getting dressed and heading for the door. I told her I was not finished with her. I told her to lay next to me in the bed. She was hesitant, but I knew she needed to lay next to me. She was next to me and I could tell she was nervous. I leaned over to her and whispered into her ear that she was a good girl and she had done a very good job. It was at that moment that she leaned into me and put her head on my chest as I lay on my back. She didn't say anything for a while. I could just feel her heart beating slower and her hands touching my body. After what seemed like 20-30 minutes, she softly said "Thank you ... Daddy". She seemed to enjoy touching every part of my body. She enjoyed touching my face and looking into my eyes. I told her she was going to be mine and she was going to enjoy it. She smiled and called me Daddy a few more times as she seemed to accept that I was going to see her many many more times.
As she touched my body I told her to lick me and get me harder again. She smiled and swallowed my soft cock in her mouth until I was hard as a rock. I carried a small bag with me into her room. It had a cock pump, lube, cock ring, and condoms. I had Tanya open the bag and she had never seen a cock ring or pump. I had her put the cock ring on me and she enjoyed how my cock bulged and became redder. She grabbed me and said "That's pretty thick Daddy". She enjoyed licking my cock. I told her that I was going to make her mine. It was now that she had some idea of what I meant. I asked her to get her toys and her lube out. She did. I had her lay on the bed, roll over, and put her tight muscular ass in the air. Her body shaking a little as if she was cold, but she was a little nervous. She had never had anyone use her toys on her. I lubed up her ass and started to put her small dildo in her sweet hole. She enjoyed how deep I could go. I slapped her ass with my cock. She knew I was going to penetrate her, but she still asked "Daddy ... are you really going to be in me? I've never had a man inside of me." I knew from our conversations that I was going to be the first cock inside of her tight hole. She wanted me inside of her, but nervously asked "Are you safe?" about a dozen times. I let her know I was. I started to press the head of my cock inside of her very tight hole. I let her know how good she felt. I told her to lean back on me slowly. "Oh Gawd Daddy ... it hurts ... but I like it" "Are you sure your safe?" I asked her if she wanted to stop. She said that she wanted to keep trying. Slowly she backed onto my cock. Slowly she moaned, in pain, in pleasure, and I kept letting her know how happy she was making me. "Good girl princess" I let her know.
When I got to the point where my entire cock was inside of her I could see her arms shaking as she was not sure how to feel. She loved having me in her, but was uncomfortable with the pain of a cock inside of her. I could tell she wanted to say something to me ... something very emotional. "You are sure youre safe ... Daddy? She then asked me if it was normal for her little clitty to get excited while a cock was in her. I let her know that is was very normal. I began to slowly pull out ... just slightly ... as I started to fuck her sweet hole rhythmically. "is it normal that my ass feels numb Daddy?" Yes, princess ... it is perfectly normal". She loved feeling my balls slap against her body. She loved feeling my hands all over her body. "You sure you're safe Daddy". I thrust myself inside of her one last time then grabbed her hips firmly. "I'm going to give it to you sweetie ... here it is" "Please ... yes Daddy!"
I released inside of her ...pumping my cock several times. She could feel my seed filling her. I pulled out and her hole was very red. She was bleeding slightly. I told her to stay bent over then I put my cock in front of her mouth. I told her to lick my balls. She lifted her head and got the rest of her red lipstick on my balls. I let her sit up and told her to finish pleasuring herself until she came. She asked me where my cum was. Why it wasn't dripping out of her. She was getting hyper and nervous. She thought she had done something wrong. I comforted her and told her that the first time her muscles need to learn to relax. She asked me to stay a while. I did. We cuddled until my seed started dripping out of her hole. I got up, got dressed, and left just as one of her roommates was coming home. Her roommate was a cute college girl who was staring at my face as I left. I got in my car and noticed I had some lipstick on my face from Tanya's kisses.
I visited Tanya at least weekly over the next year. She transferred schools and got hurt playing football. We talked daily ... then weekly ... then moths would pass. She sometimes will message me with questions about what a man likes. Deep down I know she enjoys my approval on her dress, and who she fucks ... I also know that she needs to find a real Daddy where she now lives.

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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year 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...

1 year 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...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

3 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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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

2 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

1 year ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

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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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

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...

1 year 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...

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