Mommy's Chastity Boy Part II free porn video

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Months have passed. My son has gotten used to his tiny chastity cage without complaint. I have decided to start feminizing him and so I have been giving him homework assignments in addition to his usual chores. He is required to watch at least 30 minutes of sissy hypnosis videos every night before he goes to sleep. He watches them through a VR headset that I strap to his head. Over and over he watches them. Precum pours from his cage with no relief in sight. He also gets pegged at least once a week. I have been trying to get him to cum from pegging alone, with no success. I have worked him up to taking an 8" cock. Today is his birthday. Me: Do you know what today is? Him: My birthday. I have been waiting a long time for this. Me: You mean your milking? How long has it been? Him: Over seven months mommy. Me: Do you think you have earned a release? Him: Yes! I have done everything you want. I need this mommy. Please! Me: I know what you need honey. But first I want to fuck you with my new strap-on. Him: Ok...but afterwards I get a release? Me: Yes in a way. Why don't you go get ready? Him: Yes mommy! With that, my son went upstairs to my bedroom to get ready. With him gone, I make a phone call to my fuck buddy. He's a big, black stud who has agreed to help me with something... As I enter my bedroom, a familiar sight unfolds. My naked son has strapped himself face down to the bench. His arms and legs are strapped to the long legs of the bench. His ass is raised up at waist level and his tiny chastity cage hangs over the edge, dangling. He has his latex mask on with a blindfold attached. Me: Ready for your pegging? Him: Yes mommy. I am wearing my favorite leather cat-suit with 4" inch heels. I walk over to my dresser and quickly put on my 8" strap-on. I walk back over to my tied-down son and position myself right behind his ass. Me: I need you to beg. Him: Mommy please fuck me! Fuck me please! Me: Again! Him: Fuck my ass! Peg me mommy! With that, I slam my dildo into his tight boy-pussy. He lets out a slight grunt, but otherwise remains silent. He has gotten used to this dildo -I must have pegged him a dozen times with it. I rhythmically move my strap-on in and out. As I thrust, I can feel my son move against his restraints to meet it. He is enjoying it! The little slut! The sissy hypnosis videos must be working. I can't help but smile at this. He has never been with anyone else but me. My little virgin. But that is about to change. Me: Enjoying this sweetie? Him: Yes mommy! Fuck me harder! Me: That's a good boy! (I thrust faster and deeper) Me: I'm glad you are enjoying your peggings. Those hypnosis sessions are doing wonders. Soon you will be my little sissy slut. I can whore you out to all my friends. Him: Your girlfriends? (He says this as he is deliciously wiggling his ass on my strap-on.) Me: Them. Maybe my male suitors. We'll see... Him: I don't know about that mommy. I'm not gay. Me: You seem to enjoy being fucked in the ass right now dear. Him: But you are the one fucking me. I...I like girls... not men... Me: Whatever you say dear... The pegging goes on for a while longer. Eventually, I stop and move to the front of the bench and raise my son's head. Me: I have a surprise for you dear. Him: The new strap-on? Me: Yes. But let me go get it. Don't go anywhere. I slap his ass as I leave the room -leaving him strapped down, blindfolded. I go down stairs to bring in my newest fuck buddy. He has been waiting patiently and is already undressed with just a mask on. He is massive -with the hugest cock I have ever fucked. With my heels removed, we both quietly reenter the bedroom so my son suspects nothing. Me: Ready for my new strap-on my sweet son?! I specially ordered it. It is the most realistic dildo you can buy. Stays warm and everything! (I stay behind my son so my voice sounds the same; but my black stud begins to position himself behind my son's exposed ass.) Him: I'm ready mommy. Me: Beg for it son. Him: Fuck my ass mommy! Fuck my pussy! (He eagerly wiggles his ass.) On cue, my stud enters him. His cock slides quickly in but comes to a stop just a few inches short. My son lets out a scream before the cock slowly slides all the way in. Then my stud goes to town, fucking my son's brains out. Him: Mommy it's too big! I don't think I can take it! Red! Red! Red! (our safe word -he's never used it before.) Me: Shut the fuck up! (I slide a ball gag into his mouth.) Him: Hmmmph....mmmmph!! I silently drag a large floor-to-ceiling mirror in front of my son, just a few feet from his masked and blindfolded face. I silently go back behind him, next to my stud who is still pumping away. This is a moment I have been waiting a long time for. My son has started to thrash against his restraints, but he hardly budges -he tied himself down too tight. I laugh out loud at his predicament. Little does he know that this is good for him. He needs this little push. He is a very lucky boy. Me: You know son...I have one final surprise for you! (With that I reach over and pull the blindfold off his mask.) My son, through tears in his eyes, looks at the mirror. A huge black stud has been fucking him. For over ten minutes! His eyes bulge and he begins to scream through his gag and thrash against his restraints. But to no avail. Me: Why are you resisting? This is good for you! Have you learned nothing from your sissy hypno sessions? You are little slut that deserves to be fucked! By whomever and whatever! Enjoy it! My stud continues to pound away. But I begin to notice my son ease up a bit. He is no longer thrashing around. Me: I will remove your gag if you promise to be a good boy... (He slowly nods.) Me: Ok. (I peel off the mouth gag.) Minutes pass. To my utter joy, my son begins to enjoy it. He starts to back up to meet every thrust. I can tell he is enjoying it. My stud is a like a machine. Limitless energy -just like when he fucks me. Me: Having a good time sweetie? Him: It...It...it's ok. Me: Just ok? You better be loving it! (I smack his ass.) Him: Yes mommy! I love it! Me: Tell him to fuck you harder! Him: Fuck me harder sir! Fuck me harder! My stud doesn't need to be told twice. My panties are soaking from this. This is the hottest thing I have ever seen. Minutes pass. Him: Mommy...mommy... I think I'm going to cum! Me: What?! Really? Him: YES. Mommy can I cum?! Can I cum?! Me: Yes you may dear. Him: I'M CUMMING! With the biggest smile on my face, I kneel down to inspect his chastity cage just as he begins to squirt uncontrollable through its tight confines. My son moans and moans like a woman orgasming. After an eternity my sons stops cumming, leaving his cock dripping in his tiny cage. I stand back up, an accomplished woman. My son has finally cum from ass fucking alone. I bid my fuck body goodbye (we'll fuck later) leaving me and my son alone. Me: What do you have to say dear? Him: Thank you mommy. Me: Thank you for what? Him: Thank you for making me a sissy slut! Thank you for making me cum like a woman! Me: You're welcome dear. Now you understand that since you just came, there will be no milking later. You are going to have to wait another six months or so for any release like that. Him: But... Me: Don't you understand? You no longer need those releases. I have trained you to cum like a woman. Through penetration alone! Him: Yes but...but...YES! (It begins to dawn on him.) Me: I think we can get rid of your chastity milkings altogether! What do you say? Him: Yes! I just want my ass fucked from now on! Me: That's a good boy. Permanent chastity it is. I have wonderful things planned for you. Just wait and see. One last thing dear, I need you to request this. This needs to be your choice. Him: Please keep me in permanent chastity! Keep my tiny cock locked up forever! Me: If you insist dear. You're a good boy. I give him a firm slap on his ass as I leave the room, leaving him dripping in his tight cage, contemplating his new life. -End of Part II-

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Chastity with Ex as Keyholder Ch. 07bychastity_sissy©The only light came from the crack at the bottom of the floor. I tested my handcuffs as quietly as possible, verifying there was no way to squeeze my wrists out of their cold, metal clutches. I was completely stuck.I could hear my Ex on the other side of the door. She was panting heavily. I could only imagine her Boyfriend's cock ramming her inside and out, over and over again.I guess I should back up just a little bit, although there is...

2 years ago
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my life in chastity continues a true story

Before I agreed to be locked up. Before I agreed to be an obedient chaste husband to my wife. She had sexual needs and desires that I as her husband was able and more than willing to fill. The sex was good, or so I thought. We enjoyed the intimate pleasures sometimes two times a week. Or when I had time to get into the mood.Now, since I have taken to wearing a chastity cage upon my manhood. Now that we both agreed to turn the key over to a private third party. Well, it seems her sexual wants,...

2 years ago
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mommys little bitch5

She told me that she hated all men and that they were evil basterds. after that my Mom changed forever...... After about a month Mom started acting weird. never going out, telling her friends she never wanted to see them agian. she became a hermet and pulled me out of school telling them she was going to home school me. And then she started drinking hard. One night after a an all day binge Mom was very angry she said to me all men are assholes and so are you boy maybe I should have had a girl...

3 years ago
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CHASTITY FEMINIZATION PRODUCT TESTER

CHASTITY & FEMINIZATION PRODUCT TESTER "But I'm only going to be out of work for two weeks during thereorganization," I told my wife Annie. "And they're still paying me. SoI won't really be...""Dear," she cut me off. "I don't like the idea of you being idle.Remember what happened when I was away at my sister's? For only twodays?""Honey, nothing happened. You know Tess next door is kind of... anympho. She thinks every guy wants to jump into bed with her. All I didwas talk to her, and...

3 years ago
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Chastity And Feminization Product Tester

CHASTITY & FEMINIZATION PRODUCT TESTER by Throne "But I'm only going to be out of work for two weeks during the reorganization," I told my wife Annie. "And they're still paying me. So I won't really be..." "Dear," she cut me off. "I don't like the idea of you being idle. Remember what happened when I was away at my sister's? For only two days?" "Honey, nothing happened. You know Tess next door is kind of... a nympho. She thinks every guy wants to jump into bed with...

4 years ago
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Chastity Part One

Chastity was nineteen when I met her. I was nearly twice her age. Maybe I should have had more sense than to go all mushy over a girl so young. Maybe I should have given more thought to the risk, but truth is, she stole my heart. Then she stomped it and kicked it to the curb. She was a part-time writer at the suburban newspaper where I worked back then. I had noticed her but we hadn’t met. She was thin, with brown hair so long it brushed the delicious curve of her ass. Not beautiful, she was...

Love Stories
2 years ago
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Sarahs chastity

I saw her face light up as she took the handcuffs from the rack and turned them over in her hand.I said, "You look like you've used those before."She smiled. "They remind me of a boyfriend I had in college. I spent quite a few hours in them then. It was fun, but that was as kinky as it got."Wow. When I invited Sarah up to see my shop, I had no idea she was into this stuff. I wanted to find out more, but I didn't want to push my luck, so I proceeded with caution. "Well look around anything else....

3 years ago
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The Chastity BallTuesday Chastity Gets With the Program

Tuesday - Chastity gets with The Program I was so mad about what happened on Monday afternoon that I wasn't even thinking about it might mean on Tuesday morning. It was bad enough that the school district lawyer forced me to leave the True Love Waits rally on Monday afternoon and I still ended up naked on the local news. I was shocked when Principal Johnson was waiting for me outside the front entrance the next morning. I knew that I would be expected to strip in front of everybody who was...

2 years ago
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Victoria and the ChastityGuard MK III

Victoria and the Chastity-Guard MK IIII had been observing her, and many others, for quite a while. I first noticed her whilst having a drink at the city bar where she had worked for a time. Although short, she was grossly overweight but with a strangely pretty, even attractive, face. But for the fat she would have been extremely attractive. At twenty four years of age she had not had a date for years, and never had a steady relationship beyond that of a high school friendship with a boy who...

2 years ago
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Male Chastity

Janice and Mike are a married couple in their mid forties. Married about twenty years. About ten years ago they started playing with a male chastity device and discovered they were having a lot of fun with it. They have been using it ever since.The device is a stainless steel or plastic tube about three and a half inches long and about an inch and a half in diameter with a forty-five degree bend in the middle of it. A steel ring is attached to the tube. The flaccid penis fits into the tube and...

2 years ago
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Chastity with Ex as Keyholder Part 6

Chastity with Ex as Keyholder Ch. 06bychastity_sissy©My Ex knew me. She knew me better than I knew myself. She knew it had been a deep, disregarded fantasy of mine to be a helpless maid amongst a variety of men and women, all dressed up in pretty outfits demanding drinks and snacks from the maids passing by.She had, without a doubt, put "the guy" in his place. My cock was completely locked away in full metal, and it would require an ER visit to physically remove the device without a key. I...

3 years ago
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Chastity with Ex as Keyholder Part 4

bychastity_sissy©Kneeling before my Ex exactly one week after she had discovered my chastity device and taken the key, along with several compromising photos on her phone, I was ready to do anything she asked.I know she had said all those things about keeping me locked up for a month with no orgasms, but I told myself this was only a temporary deal and she'd soon get bored and move on to something else.If you end up in this scenario, be warned that the skin under your scrotum will likely be...

3 years ago
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Chastity with Ex as Keyholder Part 2

Chastity with Ex as Keyholder Ch. 02bychastity_sissy©From what I could remember the following morning, I had definitely done something stupid. My memory became fuzzy after she had left. Just as she had predicted, I surfed the web and looked at my saved cache of porn. Unable to get off on it, I drank more and stayed up later than usual until everything became a blur and I woke up on the couch, still dressed in the corset and nylons.Good thing I had the day off.Work! How could I deal with wearing...

3 years ago
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Ginger Duck In Chastity

GINGER DUCK IN CHASTITY by Throne I sat on a kitchen chair, shifting my feet anxiously. My wife Desiree looked at me with barely restrained impatience, like she was dealing with a difficult child. Yet her green eyes held a hint of mischief. Those pale lips suggested the beginnings of a smile. I sat there trying to appear capable of reasoning with her, but that's not easy when you're dressed in a yellow top with a ruffled front and capped sleeves, and you're naked from the waist...

3 years ago
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Captain Creame Chastity Slave

Captain's Journal: February 19, 2004 Things are exciting! I have been getting friendly with this girl at work, Pamela, and taking her out to lunch, and sometimes we've taken the afternoon off work to go to the movies. Today Pam and I just went to the park and held hands and talked about our lives, and at the end of the lunch hour, she kissed me lightly on the lips. But just as she was going to kiss me again, I heard the roar of a motorcycle, and I pulled away, looking around wildly, but it...

3 years ago
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Male Chastity for the over 60s and ED corre

Male Chastity for the over 60’s.It’s interesting that all you read on Male Chastity seems to be for those in the years just after they have married and sex is getting a little dull for them so they want to spice it up a bit.My husband and I are not young he is 68 and I am 63, we have been married for some 21 years having met late in life compared to many. We have had a wonderful sex life until a couple of years ago when Ron developed Erectile Dysfunction. He had the tests, was psychoanalysed...

4 years ago
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Chastity Ch 03

King Garbin held his arm out straight through the bars, his fist clenched. Then his fingers straightened, and Kinlee’s eyes widened. Dangling from a long, golden chain that glinted in the flickering torchlight, was a delicately formed, intricate key. It swayed, and her wide blue eyes followed the tantalizing movement as her mind calculated all the possibilities. ‘Why?’ she asked breathlessly. ‘I don’t see how you will beget heirs locked in the dungeon.’ ‘Ooohh, you have a one purpose...

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