Date: Wed, 20 Jan 2016 22:53:20 +0000 (UTC)
From: chastories@tutamail.com
Subject: Roommate Keyholder chapter 5

Disclaimer:

All characters and situations are fictional. This story is intended for
adults interested in homosexual erotica. If that is not something that you
want to read or that is illegal for you to read, please stop.

Don't contact the author with commercial requests or advertising. E-Mail
contact to talk about the story, give critique, ask questions or send
messages or pictures of your own adventures is ok. This story already has
several chapters written, so any requests will probably not be worked into
it for a rather long time. Ideas and wishes are always welcome anyways.

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Each of the following days he let me suck him off and when he handed me the
key afterwards I almost hesitated to take it. If it wasn't for the dull
ache in my balls I would have told him to keep it so that nothing about our
arrangement could change. But as soon as he had left the room and I
unlocked I had jacked off twice and covered myself in my saved up juice.

I enjoyed my freedom, I'm not going to lie. But it was a bittersweet joy as
it also meant that Greg reverted back to his regular self. No strip shows
and absolutely no opportunity for me to pleasure him. It was a weird
feeling. I both dreaded and longed for the inevitable (and for me it was
inevitable) lock up. I only managed to stay unlocked for a week before I
caved. My need for Greg was stronger than my need for masturbation.

After I had locked up Greg immediately slid his hand down his sweatpants
and pulled out his already enlarged cock. I sank down on my knees and
engulfed his beautiful shaft with my mouth. I was so eager that it didn't
take long for him to shoot his hot cum in my mouth. He patted the back of
my head.

"Damn, you really went for it this time. And that after only a week of
freedom. Maybe that's a sign that you don't actually want to be
unlocked. I'll take that into consideration when I decide the length of
your lock up this time."

I expected to feel some kind of anxiety at those words but I just felt
happy. My own cock was straining against its cage but I couldn't have been
more content. I knew that sentiment would change as the days went by and I
would pray for release but at that moment I was happy.

We continued our new routine for an entire week. I would stay locked up, he
would prance around naked and horn me up all the time and once (maybe
twice) a day he would make me suck him off. I was getting hornier by the
minute and Greg knew it. Still he hadn't even mentioned unlocking me.

On the seventh day he finally told me his plan. We were sitting in our room
and I was expecting him to summon me to his bed any minute now. I had
waited the entire day for it browsing on the internet for hot pictures and
leaking into my underwear. All I could think about at that moment was
sex. But Greg didn't undress that night. Instead he talked.

"This time I'm not going for a set amount of days. Instead I'll give you
some tasks that you'll have to fulfill. Your first task is to write a
list. I want you to talk half an hour and write down every sexual fantasy
that you can think of. And I'm not talking about weird stuff that you've
thought about once.  Actual, real fantasies that you wish would come
true. Stick them into that envelope and close it."

He left the room and I began to write. It wasn't really that hard to think
of stuff but it took forever to write it down. I was embarrassed by my own
ideas even though Greg already knew about this chastity thing and was more
than fine with it. I considered leaving a few off but that felt like
cheating.  I wanted to fulfill Greg's task as best I could. After an hour I
was exhausted. I had filled almost an entire page.

When Greg came back I stuffed the paper into the envelope and gave it to
him. "What's it for?"

"Ah, I think you'll have to wait for your next lock up to find that out."
That grin. It drove me wild. My cage bounced inside my boxer briefs and I
could feel the wet spot that had formed while writing and fantasizing. "For
now we'll move on to the second task. This one will actually decide whether
you'll come out of that cage anytime soon."

I got slightly nervous. Whether? Does that mean he is going to keep me
locked for a lot longer if I can't complete his task? Is the task hard
enough for me to fail?

"Don't worry. I'm sure you'll enjoy what I have in mind for you. See, while
I enjoy what you are doing for me, I feel like I can't give you enough. I
can only come so many times before I'm spent and you are obviously still
hurting for more cock and more sexual stimulation. So my next task is
two-fold.  First for your stimulation; I've read a lot about chastity and
almost all people agree that anal stimulation is essential. So I want you
to go out and by a plug of any size you like. Unless you already own one."

I did not. I did own a dildo that I had occasionally used but I've never
had a butt plug. And since I've been locking up with Greg's help I had been
too nervous to use even that. I had already been so horny all the time that
playing with my ass had seemed like playing with fire. How would I be able
to stand that sensation on top of my already insane libido?

"What's the second part?"

"The second part is that I want you to find some guy to mess around
with. Now obviously you will only get to suck him off. Since I'm sure
you're not ready to reveal your chastity to someone just yet you won't be
getting fucked. So you'll insert your plug and find a nice boy that you'll
pleasure orally.  That should hopefully give you some satisfaction."

We talked a bit more about this task and I was just dumbfounded. What was
Greg thinking? Why did he want me to do this? He told me that he enjoyed
having that control over me and that he wanted me to make the most out of
my chastity experience. He reminded me of my own words about being so horny
that you spent all your sexual energy on pleasuring other people and that
it only follows that I should get out there and find another cock to
pleasure.

I wasn't quite sure that I agreed but I also couldn't deny that my cock was
hard the entire time we talked about it. After that I sucked him off and
went to bed, thinking about what I was going to do.

The next day I went shopping. I knew of a sex shop off campus that was
secluded enough for me to not be embarrassed. Still it felt weird to go in
their knowing that I was buying something on the command of another guy
that also held the key to my locked cock. I browsed for a while until I
found what I was looking for. Since Greg had said that I should pick
whatever size I felt comfortable with I went with a rather small one. Big
enough that I would feel something but nothing I couldn't handle for a
while. I quickly paid and went my way.

That was the easy part. That night I went inserted the plug while Greg was
out of the room. I used a generous amount of lube and was surprised at how
easily it went in. Normally it took me a few minutes to warm up but my
horniness helped apparently. I pushed it in a little deeper and let go of
an involuntary moan. I had always enjoyed that feeling but now it was even
better. It was as if I felt it throughout my entire body. I felt it slide
into place and I sighed inward. My dick was once again leaking.

Once I had it in I dressed and went outside. My plan was to go to a local
cruising place that I had heard of. I had never been there but one of my
gay friends had told me about it. It was quite a bit off campus but I could
easily reach it by foot. All the while I could feel the plug moving a
little bit with every step. Damn.

I came close to the park and hesitated. I hadn't even thought about it. I
had moved like a robot, determined to find a cock to suck and unlock my
cage. But now I was actually getting hit by the realization that I had
never had a random hook up in a public place and that I had no idea how to
approach this situation. My heart was pounding and before I could clear my
thoughts I was already turning around and heading back to my dorm.

Back in my room Greg was sitting on the bed. He looked at me
expectantly. "So?"

"I couldn't go through with it. I'll have to find someone another way."

"Oh, that's too bad. Guess you'll stay locked today. But at least you got
to play with your new toy, right? How does it feel?"

"Oh god, I'm so fucking horny. I've been wearing it this entire time and
it's driving me nuts. I have to take it out or I'll go crazy."

"Wait a moment. Since you couldn't find anyone else maybe you'll just keep
it in for now while you take care of me, what do you think?"

-

The next day I was thinking of another way to accomplish my task. Since
wearing the plug yesterday had almost driven me mad with lust I didn't want
to risk another failure so I wanted to make sure that I would find
someone. I downloaded two gay dating apps and made profiles that didn't
show my face. I made it very clear that I was only looking for a quick hook
up, nothing more. I didn't want to lead anyone on.

I was kind of shocked when just half an hour later I had found someone that
was actually willing to meet me. He had a nice picture that showed his
entire face and body and he even wrote like a halfway normal person. I had
equally high hopes and fears of being catfished. He said I could come to
his apartment in half an hour, so I put in my plug again and left my room.

The entire way I was trying to minimize the movements of the plug in hopes
that it would somehow lessen my horniness. But to be completely honest I
was enjoying it so much at the same time that I'm not sure if I actually
tried all that hard.

When I knocked on the door I was pleasantly surprised to be greeted by the
actual person that had been writing with me on the app. He told me to come
in and asked me if I wanted something to drink. He was polite but we both
knew that I hadn't come there for drinks so I declined and we just started
to make out a little bit.

Moments later I was undoing his belt buckle, slid my hand into his trousers
and started to massage his respectable member. He was cut and shaved and
got hard incredibly quick. I knelt down and pulled down his pants just low
enough. His dick sprung free and I could see that it was quite thick while
not as long as Greg's.

I started to play with his head a little bit and was delighted to see him
shiver whenever my tongue flicked over the underside of it. His balls were
deeply retracting whenever I went deeper down on his shaft.

"Wow, you're really good."

I just kept going. He caressed my head while I was bobbing up and down
rhythmically and massaged the base of his shaft at the same time. He was so
incredibly responsive to my touched that I could say without a doubt which
moves got him going the most so I could time them perfectly. I enjoyed it
so much that I just didn't want it to be over so quick. Kneeling before him
this way also made the plug move in very pleasurable ways inside of me so I
felt completely at peace.

I kept blowing him for a while when I finally wanted to taste his cum. But
then I remembered what Greg had said. He wanted some kind of proof of my
task completion. Damn. I could hardly keep his cum in my mouth until I met
Greg again. I held my head up and looked this stranger in the eye.  "Would
you mind taking a picture of me?"

He looked down puzzled. "What? Why?"

I didn't have a good answer so in my desperation I just told the truth. "I
kind of need to prove someone that this happened. You don't need to be in
the picture. I mean. Not much of you anyways."

I went back to sucking his cock hoping that this would persuade him while I
grabbed my phone out of my pocket. But before I could reach it I heard the
snapping sound of a phone camera. I looked up to him with his dick still in
my mouth and saw his camera light flash for a second. Damn, I had actually
meant for him to use my camera but whatever.

Moments later I could hear the hook up app buzz. He had sent me the
pictures. Now I was really ready to go for it. I increased my speed and
sucked a bit harder. I played with his balls and made sure to use my tongue
on his sensitive spots. Within moments I could feel him get even harder and
hear him breath heavily. Then he stopped breathing altogether before
exhaling loudly and shooting his huge load into my eager mouth.

As he pumped shot after shot into me my cock cage pressed against the
fabric of my underwear that was soaked with my precum. I swallowed three
times and enjoyed every drop of it. He tasted very different from Greg but
not bad at all. When he was done I let go and stood up.

"Wow, that was great. Do you want me to...?"

"No, that's okay. That's all I came here for today. Maybe another time."

I could see that he was confused. "Was this some kind of bet?"

"Not really. More like a task. A buddy and I have a bit of a weird thing
going on." He looked even more confused so I thought I'd leave it at that.

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I hope you enjoyed this chapter. Next one should be coming fairly soon.

If you want to speed things up I'm always happy to receive encouraging
emails with nice words, your personal stories and nice pictures. I'm
especially happy to hear from people who are new to the idea of
chastity. Tell me if this story inspired you to try it. Mail me at
chastories@tutamail.com

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