The Passage of Chastity
- 2 years ago
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Nate's Chastity free porn video
After a little encouragement, Nate's soon to be wife, Sophie, agreed to
be his key holder on the condition that it would be on her terms - 'well
fine, that's kind of the point' he thought. However, he did not
anticipate how extreme she'd take things.
Day 0, the day Nate first put on a chastity device:
This evening (Friday: Day 0) was scheduled to be Nate's first time ever
in chastity, something he'd waited a long time for. Sophie had ordered
the chastity device she wanted him to wear and had put quite a lot of
thought into the night. First he was told to strip, lie on the bed and
watch porn as she went to get changed. Nate watched her head off into the
bathroom with some lingerie and eagerly anticipated what lay ahead. Nate
naively opened up the browser on his phone and started searching for
something to watch.
About midway through the second video, Sophie arrives back in the bedroom
as he is slowly playing with himself, just enough to maintain a pretty
hard erection but certainly not enough to allow him to climax. Nate
glances past his phone to see her in a black, lace covered basque and
fishnet stockings. She has bright red lipstick and nail polish to match.
She looked very seductive and yet ready to assert control if needed.
Sophie takes a few steps towards Nate before slowly climbing onto the bed
and crawling her way up between his legs. "Don't stop watching your
porn," she tells him in a sensual tone as her head lowers towards his
erect penis. She gently moves his hand out of the way and takes over
using her mouth and hands.
She soon has him building closer and closer to an orgasm as her mouth
slides softly up and down his shaft. Nate barely gets into the next video
before he is ready to blow and, sensing this, Sophie stops. Nate moans in
almost disbelief as he arches his back. Instinctively he wanted to ask
her 'how could you stop then' but he knew the answer already. Over the
course of the next 15 minutes she gets him close another 3 or 4 times
before stopping again. She eventually stops altogether and lies next to
him on the bed. "Keep watching," she instructs as she plays gently with
his balls.
After her short break, with them watching the porn together, she goes
back to sucking. This time she's paying close attention to the audio in
the porn. As the couple in the video build towards a climax, she speeds
up her actions, building him up to climax at the same time only to stop
seconds before. As the couple onscreen orgasm in unison, Sophie peers
over the top of his phone and say. "It's time." "Now?!" he responds. "I
can't. Please, just keep going," he urges her. Nate had been on the edge
for over 20 minutes and chastity is the last thing he wants right now.
This was not unusual for him. Although Nate loves the idea of being in
chastity and finds it a huge turn on, once he gets close to cumming, the
idea of being put into chastity seems like hell. Sophie knows this and
built him up to this point deliberately. She then went to get the
chastity device she'd bought and secures it around his penis/balls. It's
a metal cage that's quite small but surprisingly heavy. It takes her some
time to get it on, all the time Nate is begging her not to but she
doesn't listen. Once on, but not locked, she looks up at Nate and simply
asks, "Ready?" He's no longer sure he really does want to go through with
the whole chastity idea at all now that it's a reality and he's so horny.
Nate hesitates for a moment before telling her that he didn't think he
could manage a few days in chastity after being edged like that. But
before he could even finish the sentence, there's a distinct metallic
click and the chastity cage is locked, and with that, his option had been
removed. "Good," she tells him, "true chastity only really begins once
you no longer want it." She is now fully in control.
She then went on to tell him in more detail what he'd signed up for.
Firstly, it's not a few days like he'd wrongly assumed. He's starting off
with 2 months - that's 61 days! Plus, if he doesn't do as she tells him,
she'll add days onto that. Nate thinks to himself there's no way he could
manage 61 days; he wasn't sure he could even manage 6. On top of that, to
prevent more days being added, she tells him he must A) make her cum
every day and B) do anything she requests. If he fails to make her cum
one day, then he will endure another day in chastity. Any objections to
her requests cause another day to be added and if he doesn't complete a
task to "sufficiently satisfactory standards" he'll have yet another day
added.
Sophie decides they need to celebrate and go out for drinks that night.
They get quite drunk and Nate starts to ease up a little. Unfortunately,
with all of the alcohol and the late night, he misses any opportunity to
pleasure her that day and subsequently gains another day to his time in
chastity.
The following morning (now Saturday: Day 1, still with 61 days to go),
the two of them are equally hung over. However, this isn't much of a
problem for Sophie but Nate has to do everything she says or risk having
more days added to his chastity sentence. That day, Nate struggles
through as best as he's able to but he still accumulates a further 3
days. He accumulates a couple more days during the week as well as he
gets used to keeping up with Sophie's requests.
The following Saturday morning (Day 8, 58 days to go), he's now just over
a week down, had his first (unfulfilling) experience of being milked, and
had only taken 3 days off the time remaining. "Seems as you'll now be
doing all of the chores around here, I've got you a little present," she
tells him. She goes on to reveal a bright pink, PVC French maid dress and
a matching pair of 4-inch high heels. Nate had no interest in
crossdressing and doesn't realise at first what she'd had planned.
"You'll look hot in those. But how does that fit with me doing the
housework?" he asks. Sophie smiles, shakes her head, and says, "Oh no,
you miss understand. YOU'RE the one who will be wearing this." Nate's jaw
drops. "I can't wear that," he blurts out in shock. "That's two days
added to your total. One for refusing the dress and one for refusing the
heels," she tells him sternly, "I also want you to keep your body hair-
free. Now go shave before you put your dress and heels on. And if you
refuse again I'll add a further 3 more days," Sophie tells him as the
volume of her voice rises. By the end she is almost shouting at him and
he had no leverage in the conversation.
Sophie sends him off to the bathroom for him to shave his body. It takes
a while but eventually he returns to find Sophie has left the dress and
heels in the bedroom for him. First he goes to his underwear draw but to
his horror everything's been replaced with knickers and bras. Grumbling
to himself, Nate takes out the set that was on top: a basic knicker and
t-shirt bra set that are made from a material that's as pink as the
dress. 'They're just underwear,' he tells himself as he slips on the
knickers. Hanging the bra from a couple of fingers, he wonders whether he
really needs to wear it.
Nate goes downstairs feeling rather embarrassed already in just a pair of
pink knickers to find Sophie. "Do I have to wear this?" he asks in a
defeated tone as he holds the bra up for her to see. "Yes," is all she
responds as she gets up from the sofa and walks over to him. Sophie takes
the bra from his fragile grasp and slides the straps over his arms. She
then walks behind him and fastens it securely. "Now, the next time I see
you, you better be in your dress and heels or I'm adding more days on,"
she explains.
Nate meekly leaves to go finished getting dressed, feeling well and truly
defeated. He picks the dress up and pulls it over his head. Getting the
zip pulled up at the back is a new and challenging experience. Once done
up the dress hugs much of his body and feels rather strange. The smooth,
shiny and yet hot material is not a sensation he particularly enjoyed.
The short flared skirt swayed gently around his thighs as he moved,
making him feel very exposed knowing that underneath was a pair of
knickers. Next he put the high heels on - they're tight and very
difficult to walk in. He's barely able to stand in one spot, let alone
walk with any elegance. He somehow makes his way downstairs holding on
tightly to the banister so not to fall.
"Perfect," Sophie says the moment she sets eyes on him again, "now you've
completed most of your chores during the week so I want to use today to
teach you how to walk, sit and stand in a dress and heel." She has him do
all kinds of activities while shouting things like 'knees together',
'back straight', 'head up'. He's drilled all day and by the end of it
he's feet and calves are killing him from walking and standing in heels
for hours. "Now, I've let you off easily today but any deviation from
what you've learnt will result in the usual punishment of additional days
in chastity. Do you understand?"
"How often do I have to wear this?" he asks. "I've got a couple more on
order so you can wear your normal clothes tomorrow but after that it will
be every Saturday and Sunday. Understood?!" she asks again more forcibly.
"Yes, ma'am," he response as she'd taught him earlier in the day.
Three weeks later (Monday: Day 31, 41 days to go), Nate is now a
perfectly obedient maid whenever he's at home. Sophie has not permitted
him to wear trousers for a week now except for when he goes out. He
hasn't quite gotten used to doing a bra up, the feel of a dress, or
walking in heels, but at least he's refined his abilities enough to
minimise the number of days in chastity that keep getting added to his
tally. However, he'd been dreading today since finding out he'd be in
dresses full time at home. Today, Sophie's book club (Lizzy, Kate and
Sarah) was meeting at their house.
Sophie's friends found Nate's predicament very amusing. They had a lot of
questions and the group spent more time talking about Nate's uniform,
chores and chastity than they did about the book. Nate spent much of the
evening fetching the ladies drinks and the rest of it waiting in the
corner of any further requests.
"So you don't have sex?" asks Lizzy.
"No, but I still get some," Sophie replies.
"You mean like cuckolding?" Kate asks with some shock.
"What's that?" Sophie enquires taking her phone out to google. "Oh no, I
meant I make him pleasure me. I don't want to miss out just because he
has to."
"You know you could get a strap-on and make him wear it?" Lizzy suggest.
"Yeah. With him wearing it, you two could still have sex," Sarah adds.
Sophie ponders for a bit. "That would be nice. I do kinda miss actually
having sex."
The ladies begin browsing online for strap-ons and come across a few
varieties while Nate looks on in horror. Sophie eventually picks out one
and orders it using Nate's card without Nate knowing exactly what kind
she had purchased.
That evening, after Sophie's 'book club' had left, Sophie turns to Nate
as says, "You know, I was thinking. I like to try to up the ante
throughout your time in chastity - you know I don't like to stagnate."
Nate thinks to himself, 'Oh God, what could she have planned this time.'
"What do you think to being my cuckold?" she enquires. Nervous about
going against his key-holder but not wanting to be emasculated that much,
he replies with a sheepish, "I don't know. I know it was my idea to make
sure you still get pleasured sexually while I'm in chastity but that's
not what I meant. Plus this is bad enough as it is." Before this whole
chastity escapade began, he might have found the idea of mixing chastity
with cuckolding a turn on. However, the reality was very different and a
month in chastity changes your perspective somewhat. "Here's the deal: if
I happen to find a guy to go along with this, I'm going to add two months
to your chastity for every time he makes me cum. But if your chastity
ends before I find someone, you'll be safe from ever being my cuck," she
tells him. Sophie had no intention of ever doing that and Nate knew it
deep-down. She'd only said it to tease him and it worked. There was
sufficient doubt in his mind to keep him inline so that no more days were
added to his chastity. Nate tries to protest but Sophie threatens to add
more days to his chastity period for doing so, so he very quickly stops.
A couple of days later (Wednesday: Day 33, 39 days to go), the strap-on
arrives and Sophie decided they should try it out that night. With Nate
naked except for the chastity cage and Sophie in a robe, she removes the
part designed to sit inside a woman before handing it to Nate. He, fully
humiliated by being made to wear a prophetic cock while his real one is
locked away, docilely steps into the leg/waist straps before securing
them in place. With the fastenings tight and the strap-ons penis sitting
comfortably above his own, Sophie moves forward to touch it. "Oh, it's
bigger than you are...erm, were," she tells him with a gleeful smile,
correcting herself as if he was never going to be erect again. She flicks
a switch on the box attached to the waistband and it starts vibrating.
"I'd bought some lube but I don't think we need it," she says while
smiling uncontrollably.
Sophie removes her robe to reveal the same sexy underwear she wore when
first putting Nate into his cage, except this time without any knickers.
She lies down on the bed and beckons him towards her. He climbs onto the
bed between her legs and lowers his body on top of hers. She takes
control of guiding the strap-on where it needs to go. As he slid into
her, it was clear this new toy was doing its trick. The vibrations
combined with the extra length and width compared to Nate's erect penis,
quickly brought Sophie towards a climax. Nate, on the other hand, was
fighting against a building erection. Having Sophie moan and squirm in
pleasure beneath him, while he rhythmically thrusted as if he was having
sex, triggered him to become even more hornier than he'd been up to now.
Sophie began moaning louder and louder, and with that he involuntarily
built his rhythm for longer and deeper thrusts, as he would do if they
were actually having sex normally. Sophie quickly climaxes and hugs Nate
close as she does. She lies under his weight, with the strap-on still
vibrating within her. "Ooh, you're never coming out of that cage. That
was incredible," she whispers to him.
As the weeks go by (now Day 50, 25 days to go), Nate becomes more skilled
with the strap-on and, as this becomes the new norm, he stops needing to
fight so hard against developing an erection while using it. Then Sophie
suggests they switch it up; while holding the strap-on aloft one evening
she asks rhetorically, "How about I wear it tonight?" Nate feels a pit in
his stomach hearing those words. It had crossed his mind that Sophie
might suggest this sooner or later but hoped she never would do. He knows
he can't say no. After Nate gives a submissive nod, he's instructed to
get onto all fours on the bed as she gets ready. Sophie puts it on and
adjusts the straps to fit her body instead of his. Once secured, she
turns the vibrator on for the part that is sitting deep inside of her
and, unprepared for the power of it; she instantly goes weak at the
knees.
Sophie positions herself behind him, applies a healthy amount of lube to
the strap-on and his arse. She lines the head of the strap-on up and
slowly begins to add pressure. It doesn't take her long before she slips
in. "Wait, wait, wait," Nate calls out in reflex. "Don't worry babe. I'll
be gentle, she tells him in a patronising tone. Soon she's pushing harder
to go deeper into him before smoothly moving most of the way out again.
With one hand around his waist and the other bracing on his back, she
starts increasing the speed and depth of the thrusts. Nate cries out as
his arse is being stretched.
Sophie loves the power; the authority that's come from Nate being locked
in chastity, the feel of the vibrator pushing into her from the
resistance as she pushes into Nate, the control she has over him and over
the whole situation. She has all the power right now but she's losing
control of herself as she becomes hornier and hornier. The more she
thrusts into Nate, the greater the feeling from the vibrator pushing into
her. She can't help but thrust harder, deeper, faster, again and again.
She fucks Nate for several minutes building ever closer to a climax and
as she does, she notices soft little moans from Nate in between her own.
"Are you enjoying this?" she asks, truly intrigued. Nate lets out a
whispered, "Yes," ashamed to admit it too loudly.
Not long after, as she's building faster and faster, she climaxes with a
powerful orgasm that halts her movements. Eventually regaining her
composure after a few seconds she notices Nate asking her to carry on.
After several more minutes of receiving anal, Nate is still unable to
climax, however Sophie does for the second time and with that loses any
strength to continue. She slumps down on the bed next to him and he, also
weary but significantly unfulfilled, lies down too. With a relaxed
exhale, Sophie turns to Nate and says just, "Wow." Sighing in
disappointment Nate responds by telling her that he felt like he might
have actually cum then. "I'm glad you didn't. You are in chastity for a
reason," she tells him with a sadistic smile on her face.
Day 85, Saturday morning, and Nate had finally got his tally down to one
day to go. He woke up that morning alone in bed. Sophie had gone out the
previous night and planned to stay at Kate's house. This didn't mean he
was able to relax that morning though as he still had to complete a long
list of chores that day if he did want his chastity cage removed the
following evening. He gets dressed in his maid uniform and heels, which
had become standard for him by now. He's not been dressed long when his
phone goes off with a message from Sophie. He opens it to see a picture
attached of her in bed with a large black man and a message that reads
"oops, looks like you're now my cuck :)." Nate is stunned and has to sit
down to stop himself toppling over in his heels. Then another message
arrives: "BTW, you've had 4 months added to your chastity and Aaron wants
to make it another 2 before he gives me a lift home." SIX MORE MONTHS!
Nate's had so far endured almost 3 and in that time has been completely
dominated and feminized in numerous ways. Now, with the end in sight,
he's suddenly had his chastity extended to be 3 times as long and in
possibly the most emasculating way he could imagine. Then his phone goes
off a third time. "Make sure you're wearing your maid uniform when I get
home, Aaron wants to see. Just between us two, I'm not sure if he's got a
little kink for French maids."
Day 187 (203 days to go), it's been around six months and Sophie's had to
stop adding on days every time Aaron makes her cum. It is now Nate and
Sophie's wedding day, or more specifically wedding night. Sophie had Nate
wear wedding lingerie under his suit. He'd worn a white satin basque,
matching thong and white stockings (and of course his chastity cage).
Luckily for Nate, his black jacket and waistcoat generally did a good job
of hiding what he had on underneath during the ceremony. Now in the
bridal suite, Sophie had Nate undress down to his lingerie and lay on the
bed. Before Sophie is able to undress, there was a knock at the door.
Sophie walks over to Nate and gives him a single lingering kiss before
saying softly, "That'll be your surprise." She makes her way to the door
still wearing her floor length, princess-style wedding dress and opens
the door. Nate remained hidden from view so not to be seen but he could
hear clearly Aaron's deep voice say, "Hi babe," as the door opened. "Hi,
come on in," Sophie responded almost instantly before stepping aside to
allow him to enter. "Now you two have fun," she tells Aaron before
walking out of the room without saying a word to Nate. Nate watches
Sophie walk down the hallway, she doesn't even turn back as Aaron slowly
closes the door. Nate heart is filled with dread but Sophie knew without
doubt that Nate would make her proud.
Emely
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