Date: Sun, 23 Oct 2016 22:44:39 +0200 (CEST)
From: chastories@tutamail.com
Subject: Sixty-five - Chapter 1

Hi! I haven't posted anything in a while. I'm sorry. Here is a new story
that I hope you enjoy.

(gay, domination, chastity)

---

"Fucking faggot", she had screamed at me. "Get the fuck out of my
apartment!"

Fuck, I thought. How the hell had she found out about it? I really thought
I had been careful enough but somehow she knew that I had cheated on
her. She has said she'd followed me around someday and seen me get into a
strange man's apartment. I had tried to lie my way out of this mess but she
wouldn't believe me.

But it didn't matter how she had found out. She knew and now it was over
between us.

My sex life surely hadn't been perfect but she had provided a place for me
to stay and had even helped me pay my bills when I didn't have enough
money. Damn. Why did I have to cheat on her? But I know the reason all too
well. My fucking cock. I just had no control over it. Whenever I got horny
I just lost all inhibitions and did whatever I had to do to get my rocks
off. I've never even considered myself gay but when the opportunity had
come to get sex regularly without the hassle of having to seduce Jennifer I
had just jumped on it.

And Jake sure as hell delivered. Whenever I felt like it I just stopped by
his place. Most of the time I didn't even announce myself. I knew his work
schedule and he was always ready. Whenever I rang his doorbell my cock
would stiffen in anticipation. As soon as he'd opened the door he would
pull me inside and get to work.

My trousers would come off in a matter of seconds and my already hard dick
would be in his mouth.  And what a wonderful mouth it was. Whoever said
that men where better at sucking cock must have known what he was talking
about.

I had never come as fast as the first time he had deepthroated my entire
shaft. My cock went in and out of his throat while his hands massaged my
ass. His finger tickled my hole and I wanted to protest but he thrust my
entire cock down his throat again, making me moan uncontrollably. Before I
had realized it, his finger had been inside me, playing with my ass and it
felt incredible. I didn't know whether it was his throat or his finger that
pushed me over the edge. I remember warning him about my orgasm.  He had
just grabbed my ass and pushed even deeper so that I shot my load right
down his throat.  Amazing.

It had taken some time for me to get used to having sex with a man but once
I had gotten over it I was in heaven. Over the course of the last year I
must have had more sex than ever before. A few times I had even
reciprocated. We had both been naked and Jake had inched closer to a
position that allowed for mutual oral sex, so I just tried it. At first it
felt weird to stroke another man's penis and to suck him off but I got used
to it. I kind of liked it even.

But as soon as I had ejaculated that feeling was gone. I could never get
myself to suck him off, once I had come. Most of the time he just jacked
himself off while he stroked my muscles or nursed my softening cock in his
mouth. But after I had discovered the joys of anal sex, things changed
anyways.  Whenever I fucked him he would just masturbate. All I could think
about in that moment was my own cock. The feeling was just too amazing to
concentrate on anything else.

---

As I walk out of Jennifer's building I couldn't help but think to myself
that it had been worth it. But now I had to worry about the
consequences. She had packed two suitcases with all my belongings and
thrown me out of her apartment. I didn't have anywhere else to go. My best
friend, Mike, lived together with two other people in a tiny apartment. And
I sure as hell couldn't call Christian, Jennifer's brother. We were friends
but he would definitely be mad at me.

The only other person I could think of was Jake. His place had enough room
for at least two people and we'd known each other for a year now. Also, he
was at least a little bit to blame for my homelessness.  ---

"You want to live with me?"

"For a while, at least", I answered. "Jennifer found out about us. I have
no place to go."

"Look ... You're a nice guy, Derek, but I'm not sure about this."

This is the moment where I started to panic. I didn't have enough money to
rent a hotel room or get a new place for myself. I had to convince him.

"Please. There must be something I can do to make you change your mind." I
stroked my hand across the bulge in my jeans suggestively.

Jake was quiet for a while. Then he smiled. "There is something you could
do for me. Undress!", he said and left the room.

For a moment, I stood there confused. Normally he loved taking off my
clothes or watching me do it but then I heard him in the other room, going
through his closet. He was looking for something.

I undressed and threw my clothes into a corner. In the mirror, I could see
myself. Naked. I had been to the gym a lot lately and it was paying off. I
heard Jake opening the fridge now and then coming back. I lay down on the
sofa, crossed my hands behind my head and waited. A blowjob would be nice,
I thought.

Jake came in with a little bag in one hand and a blindfold in the other
one. The blindfold was for me.  He put it around my head, made sure that I
couldn't see anything and proceeded with his business. I didn't know what
to expect but my experiences with Jake made my cock hard already.

"Oh, don't get too excited just yet", Jake said. Then I felt something cold
on my dick. Ice cubes. He rubbed them all over my groin, effectively
killing my boner. It was a weird feeling but I kind of enjoyed it.

"Good boy", he said and put the ice cubes away. The next thing I felt was a
cock ring that he pulled over my penis and my balls. It wasn't very tight
though so I didn't immediately get hard again. Then I felt something
different. He pushed my cock into something hard. Some kind of tube but not
as soft as the pocket pussy that I had once bought for myself. But it fit
my cock perfectly, encasing it completely. It felt nice. I wanted to lift
the blindfold, but Jake slapped my hand away.

"Be patient", he said and went on fidgeting around my groin. A few moments
later I heard a click followed by Jake clapping his hands together in
satisfaction.

Next thing I knew he was standing on the couch, his dick right in front of
me, as he told me to open my mouth. By now it had been at least a few
months since I had sucked his cock but if that was what it took for him to
let me move in with him I wouldn't protest.

I reached out and grasped his cock. It was as big as I had remembered
it. Jake had once told me that it was 7.5 inches long. Slowly I started
sucking it, tasting the unique flavor of his dick. I moved my head forwards
and backwards, jiggled my tongue across his frenulum and stroked his shaft.

Jake moaned whenever I his cockhead hit the back of my mouth. He grabbed me
by my hair and slowly started to take over the rhythm. His cock went in and
out of my mouth, sliding between my lips while my hands played with his
balls. A few times he went in so deep I could almost feel my gag reflex
kicking in just in time for him to pull back again.

This was a completely different experience to our normal sex dates. He had
never been this controlling but I didn't complain. I liked to try new
things and this was kind of turning me on. I could feel myself getting
hornier, my dick trying to harden, straining against the tube. I couldn't
get a hard-on in this thing, whatever it was.

I tried not to think about it and concentrated on Jake's cock. His moaning
was getting loader and his movements more rapid. I knew this could only one
thing and tried to get away. He stopped me though, holding my head even
tighter and ramming his cock into my mouth at an even higher speed.

"Fuck!", he exclaimed. "I'm coming."

A tremor went to his body, making him almost lose balance and his cock grew
even larger. The veins on his penis pulsed noticeably and something hit me
at the back of my throat. His jizz came, spurt after spurt, threatening to
spill out of my mouth. It tasted salty, but also kind of sweet. Not at all
what I'd expected.

In that moment, I didn't even think about it. I was so horny, my cock
painfully restrained from growing to its full size, that I just swallowed
it. I was so overwhelmed by the feelings I had, that I collapsed back into
the couch and sighed a sound of relief. Maybe I was bisexual after all.

"Well, you performed nicely." Jake fell down next to me and put his hand
around my shoulder.

"Thanks", I giggled. "Does this mean I can stay with you?"

"Well, that depends", he said while taking off my blindfold. I looked down
and saw the thing that he had put around my cock. A transparent plastic
tube that was attached to the cock ring. It encased my penis perfectly,
making it impossible to get an erection. And there was a lock. I looked at
it confused.

"It's a chastity cage", Jake said. "I bought it a few months ago for
another hook-up. He was really into being submissive and servicing me. Ever
since then I wanted to try it on you but I never had the opportunity to."

I was getting a little bit nervous. The lock seemed secure enough and there
was clearly no way for me to just slip out of it. I was trapped in this
unless Jake gave me the key.

"We can take it off now." Relief swept over me. "But..."

Jake stood up and went to my luggage. "If you want to stay with me you must
wear it for a while. To be completely honest I kind of had enough of your
selfishness in the bedroom."

I gulped. Fuck. What had I gotten myself into. I couldn't go back to
Jennifer. She would never take me back. Her brother was out of the question
and I'd rather not explain this whole situation to my buddy Mike. What was
I to do?

"How long?"

"Well, let's see. We've been seeing each other for about year now. You came
by at least twice a week.  Let's say we slept with each other a hundred
times. If we say that you helped me achieve an orgasm about a third of the
time that would leave you about sixty-six orgasms in my debt."

Holy crap. I could feel my stomach sink.

"Minus this wonderful blowjob you just gave me leaves us with 65 orgasms
that you owe me. So... If you want to stay with me, you'll have to make me
come 65 times."

"You... you want me to get you off 65 times before you'll release me from
this thing?"

"Don't worry. I really enjoy your company. If you want to you can get at
least two loads out of me a day." He smiled.

One month. One month in this hellish device. My cock twitched inside it. It
was struggling again, trying to get hard. Damn it, why was I so horny? My
head was spinning. I was looking for another solution but I came up
empty. I couldn't say no to this arrangement or I would be out on the
streets.

"Okay."

---

Hey, I hope you enjoyed the first part of this story. I wrote it a while
ago and never got around to editing but since I haven't been producing
enough content lately I thought I'd give it a quick edit and send it in. If
you enjoy it I'll edit the other chapters as well. There are several
already written.

Other stories:

http://www.nifty.org/nifty/gay/college/roommate-keyholder/

https://www.nifty.org/nifty/gay/relationships/making-me-choose-chastity
(sent in with a disposable email address a while ago)