Chastised Pt. 02

The complete story of how I ended up chaste and losing my freedom can be found in "Chastised Pt 1".

If you have been following my story you know that I have created a monster.

The monster is my girlfriend, Ann. Ann is only 5'3" with a cute little shape, including a perfectly round ass. Her pussy, was a thing to behold.

Unfortunately, I introduced Ann to chastity. Mine, not hers.

Ann has fallen in love with keeping me locked up. For me, the thought of locking up my cock so I couldn't do anything but pee was titillating at first, but the more rigid her rules and demands became the more frustrated I got.

Ann experimented with several penis locking devices and requested I model them and give input. I found out later this was only so I wouldn't get sore or injured during long term use.

Claims of "This is uncomfortable" were then crossed off the list of reasons for freedom. Not sure this was ever on the now empty list anyway.

Ann will video chat me, sometimes in the middle of the night and ask to see the cage on.

Occasionally she will demand, within minutes, I send her a picture of it.... in front of her picture on the counter....or next to the TV remote.... or soaking in a bowl of ice water, yes she has done all these and more.

She said if she does ever catch me without it on, she will "go see Neil"

Fucking Neil, the fabricator of my prison. As you read in chapter 1, Neil is an expert in metal and plastic fabrication and also knowledgeable in computer programming and app development. He designed and manufactured this little chastity cage and has a very obvious interest in fucking Ann.

Neil lives a few doors down the road from Ann's condo and openly flirts with Ann and she openly flirts back.

It makes me sick every time we go somewhere and he's outside yelling, "Looking good Ann"! and she yells back, "Wow, look at you, working out more I see, Neil"!

He then will give me a little smirk as he knows I'm wearing the cage and is the cause of my consternation.

Fucking disgusting and makes me want to pummel him.

Anyway, she considers removal of the cage cheating on her because "Why else would I remove it?" and if I cheat on her she will cheat on me as all she has to do is walk 50 feet down the street.

I have not been able too, nor have i tried to remove the cage without her permission since she gave me the "Neil Ultimatum".

So that's my trap. I have to leave the cage on which doesn't even allow me to beat off, believe me, I've tried.

I have had 2 wet dreams in the last two months but they are difficult to enjoy while sleeping. Apparently, they can be caused by high levels of fluids in the testicles due to lack of ejaculations.

While I would love to relieve myself of these pent up fluids I decided not to tell Ann about them. I have read of other men in this situation forced to go through the process of milking the prostate to drain the balls. This stops the wet dreams. This can be done without penis contact making the process unenjoyable. My frustration level is high enough. Let's not give Ann any ideas.

Today I flew into San Francisco for vacation and I met her and her teenage son Dillon at the airport. She made a point to show off a key on a necklace around her neck. I assume that's the key I need. It's been two weeks of "lock up" since I've seen Ann and even then she played a twisted game that ended with "no joy". Well, no joy for me but SHE was very "joyous" and showed it for days, but that's a different story for a different time.

It was late when we arrived at the airport and on the Uber ride to the hotel, Ann took advantage of the dark to do a quick check that my cage was in place. It was.

We checked into the hotel and while Dillon was in the bathroom Ann said, "Look, I know you're frustrated and I want to give you a chance for "early release".

I wasn't aware I had a release date.

My ears perked up.

She then handed me a piece of paper. It read:

"Rules,

Tonight it's late and we are tired from traveling. When Dillon falls asleep you can rub my pussy if you would like, that's it, you get nothing tonight.

Beginning tomorrow we are here for 6 more nights.

Every night we'll have a different event.

It will begin with me sending Dillon in to take a shower.

Put your phone on silent.

The shower is the start and stop signal. Shower on, it begins, you are allowed to cum, shower off everything stops including your time to cum.

Every night, before we do any of the events mentioned here, you need to get me off because my needs ALWAYS come first.

AFTER that, we'll focus on you and I will do progressively more stimulating things to you with each of the 6 nights we are here.

Again, when the shower shuts off you are done for that night!

First night I will just kiss you.

Second night I will kiss you and play with your nipples.

Third night I will grope your balls while licking the tip of your cock through the slit in your cage

Fourth night I will massage your prostate while pinching your nipples and licking your tip through the slit in your cage

These last 2 nights you will be allowed to remove your cage after my orgasm. Lucky you.

Fifth night I will put just the head if your cock in my mouth and might do some light licking.

Sixth night you can actually fuck me, something you haven't done since, gosh I don't know when.

If you cum, you cum. If not. I don't care. But you can only cum while I am in contact with you. You are not allowed to rub yourself with anything.

When the shower shuts off we both stop whatever we're doing.

On the fifth and sixth night, when Dillon comes out you will need to go into the bathroom, video call me, mute your phone and show me that you are putting that cage back on correctly with no "unnecessary movement". I will keep the key around my neck and watch you padlock your cage securely, giving it a tug.

Failure to follow any of these rules disqualifies you for the night. If you are caught without your cage on, delay the bathroom video call or try to beat off at any point, that's cheating and I will be forced to cheat on you with a visit down the street as soon as I get home."

That was the end of the "rules" and I sat there just trying to process it.

"I think your odds of cumming on nights five and six are pretty good, huh?", Ann said.

"Yea", I said quietly, of course they are I haven't come in like 2 months.

I was still trying to absorb all she said.

Of course, my preference would be to skip to nights 5 or 6 but this was obviously more than I could ask of my power hungry monster. So the 6 step plan to my orgasm will have to do.

Though content, my mind kept going back to the "Neil Ultimatum." I don't like him and the thought of him fucking Ann makes my stomach turn.

Nothing really to say. She wasn't asking permission, she was telling me what was going to happen. She was in control. It was her world now.

That night I rubbed her pussy, she came, I didn't, but my shaft certainly found the confines of its unyielding prison.

That first day of sightseeing was tough. All I could think about was my cock and that pussy. Alcatraz huh. That's what I'm wearing, "'lil Alcatraz"!

The first night went as predicted. I got her off and she kissed me for about 20 minutes before we heard the shower shut off. I was "hard" but not near orgasm. I liked Dillon's long shower though. Yes! Keep it up dude!

The second night was much like the first. Although I thought I got half way to an orgasm with just nipple play, not sure that it would have actually been an orgasm or just my balls exploding after 2 months' worth of teased cold storage (minus 2 wet dreams).

The third night I got Ann off with ease and she began stroking my balls and licking my tip through the slit in the cage. It was feeling very good and I thought, in my condition, this could work. But eventually, shower off, it wasn't to be.

Fourth night, now we are getting somewhere. The stimulation and frustration levels combine to make my orgasm something that could happen at any moment. Touch or no touch.

I hate to brag but I'm pretty good at getting Ann off and with all this on the line I was on top of my game. The faster I could get her off the more time I had to get off on her ridiculously light stimulation. It seemed she was trying to slow things but I was having none of it. I licked that clit with perfect strokes, swirls, pressure and coverage. In concert with proper hand and finger placement. Yep, she blew.

Now my turn.

She shoved her finger up there as promised and licked my tip through the slit in the cage and as a bonus massaged my balls. This was good. I have never had a prostate only orgasm but I hear they are great. Its building and building, I feel it starting. Then the shower, the fucking shower shut off. What was he doing? Why a short shower? He came out and Ann inquired. He said he wanted to watch a TV show. Ann just smirked at me.

I missed out on what could have been the best orgasm of my life and instead got a light, no penis contact, prostate milking for some stupid fucking high school drama fucking TV show. I shook my head the entire time it was on. FUCK!

Well, I still have nights Five and Six maybe both. I wonder, when I cum on night five do I still get to fuck her on night six? Not going to ask. We'll cross that bridge....

Night five, yay, shower starts, I get her off with all the skill of a senior tradesman working his honed craft.

I finally get to take "lil Alcatraz" off, it wasn't easy as I was fairly erect in it. No way that was going to stop me though.

She instructed me to kneel on the bed, I complied. She then got on all fours and put the head of my dick in her mouth.

It seemed like she was doing her best to not move her mouth or tongue at all.

Frustration level, 10!

I said, "Come on your rules said light licking. We are following your rules right"?! My comment came out with a bit more angst than intended

She looked up at me with a glare I hadn't seen before which told me I was in uncharted waters.

She spit it out and with anger in her voice said, "The rules say I "might" do some light licking. Would you like to call a "time out" and review the rules?"

I said, "no, no, my mistake, sorry".

But she got up anyway to retrieve the sheet of "rules" and pointed out the word "might."

"I see, I see," I said, "you're right."

I just wanted to get my cock back into that mouth even if it was just the tip. After the "rules refresher" and a good long glare, she obliged.

This had wasted about 3 minutes of my precious "head-in-mouth" time.

However, in my mental and physical condition it only took about 30 seconds and things started moving along swiftly.

Spasms were causing me to jerk and increase th movement of her mouth on my head resulting in increased pleasure. I soon found myself fabricating spasms to cause this pleasure more often. She must have known my ploy but allowed it anyway. Maybe she's going to let me cum. Maybe I can finally get satisfaction after months of denial.

I think I'm going to lose it right here. I need to tell her. I had been warned that I couldn't shoot my load in her mouth and if I did she would never blow me again. So I need to warn her soon.

Wait, if I warn her and pull out of her mouth the stimulation would stop and if I'm not allowed to touch it and she doesn't touch it then it will be a ruined orgasm. No. What should I do? I'm very, very close now.

The shower shut off.

She removed her mouth..

No!

At this point apparently I entered an altered state as never before.

After months of teasing and denial my brain finally snapped and everything then got a little weird and fuzzy.

My body took over. My consciousness shut down

I was disconnected from reality and my hips naturally thrusted in an attempt to continue my stimulation.

Be it natural instinct or biologically determined, I continued with this out of control reaction.

I "woke" to the sound of Ann laughing and the sight of my uncontrolled rock hard cock fucking the thin air right in front of her face.

I had "blacked out", and cannot recall to this day what I was doing this before I came back to reality.

"Don't stop", I begged. She revisited that glare and said, "We are following my rules, right?"

Ann then escalated my embarrassment even more with her now roaring, snorting, belly laugh resonating through the hotel room in a manner that revealed the ever evolving monster that I am guilty of helping to groom.

The switching from glare to laughter was almost chilling.

She then told me with glee that during my "blackout" I was trying to reach and fuck something which resulted in me humping the air for about 10 seconds until I finally regained my senses.

How embarrassing. I hope no one finds out. I hope she doesn't tell anyone.

Dammit, this kid usually takes 45 minute showers. I was very near the point-of-no-return and your shower ended?

Now, 2 days in a row while I'm finally being properly stimulated, he takes 15 minute showers. Fuck!!

I can't believe it. I tried not to let my frustration show when Dillon came out from the bathroom. Still in my delirium, I'm not sure how I asked about the short shower but I did. He gave an explanation just as short, "No hot water."

Ann pointed me to the bathroom smiling and gave a "call me" gesture with her "hand phone" to the side of her face.

While in the bathroom, replacing my cage, on video chat, I checked, sure enough no hot water. I heard Ann laughing out in the room. Apparently, watching me check for hot water. Fuck! Fucking cheap ass hotel.

Things just aren't going well. My balls hurt. Never before have I had "blue balls." I now know what they feel like.

I'm not liking this game. Every time my frustration level goes up it just matches Ann's escalating level of enjoyment. I am beyond annoyed.

I swear I walked around the entire next day with "wood." Alcatraz? huh.

Ann on the other hand was laughing and giddy all day long. She kept saying "5 to 0" comparing her orgasms to mine. I guess we're keeping fucking score now. She even wore my favorite little short black skirt which showed her underwear with every San Francisco breeze and San Fran is breezy. She was discrete with it, at first, when a man would be checking her out she would let the breeze "do its thing" and give him a little show.

By the end of the ferry ride she must have found a way to sneak her panties off. I swear I saw that lasered pussy that I haven't been allowed to touch in months when one of those breezes came up. Then she went a step further. Ann bent over facing me giving the man standing alone behind her a great show including separating her feet a bit too much. From the frozen look on his face he must have seen that spread pussy. It was probably wet too. A better show, for sure, than my angle looking down her blouse. Fuck!

All this "mind fuckery" has caused me to leak like a sieve and it was becoming noticeable with a spot on my pants. Ann sat on my lap. Hugged me and whispered in my ear, "I see you're having problems with excess fluids. I've been reading about this. I believe I know how to reduce your fluids. Don't worry, it won't involve any pleasure.....for you." Her laugh seems to be most hearty when it's at my expense.

That evening my frustration level is off the charts and we are eating at a downtown restaurant.

Suddenly I ask Ann and Dillion, "Do you guys feel that?"

Ann asks, "Feel what?"

"The vibration coming up through the floor."

They both look at me blankly and say, "No".

I soon realize I'm the only one feeling the vibration because it's actually me.

I pretended to just shrugged this off as me "imagining things" and went back to eating. I know I wasn't imagining things though and discerned that it was my blue balls, prostate and pelvic floor all spasming in a pre-prostate orgasm.

OMG, I'm so horny and pent up I almost had a mind induced physical orgasm. Can that happen?

That would have been embarrassing right here at the table.

That night after Dillon went in the bathroom Ann said, "Good Luck" to me. Ridiculous statement, I knew full well I would need no luck at all. At my pent up frustration level maybe 3 strokes inside that tight pussy was all I would need to blast my load deep into her walls.

The shower started and I went to work. Ann must have been excited too as she came in record time. Awesome! My cage came off and I was ready to go.

I now figure I have at least 20 minutes to fuck her. Only needing about 30 seconds it was money in the bank. I hopped up on that mound with reckless abandon. She was already naturally lubed from her own juices and my cock slid into that pussy like a hot knife through warm butter. I hadn't felt her pussy with my fingers let alone with my cock for months but it seemed more like years. That first penetration was pure ecstasy and I knew I would be in the throes of orgasmic waves within seconds. I pulled back and thrust deep into that cunt all the way to my balls. The feeling? Like the world was mine. I had it all. King for a day. A feeling unmatched by any drug real or imagined. Moments away from the best orgasm anyone in the world has ever had. I pulled back for another, possibly final thrust and....

Suddenly my text message tone went off on my phone.

Ann pushed me back while pulling that perfectly wet pussy away and my cock was suddenly very alone. "What?"

"Your phone was not on silent," Ann said.

"Yea well it's quiet now. Get that pussy back here," I said "I was seconds from finishing."

"That's too bad." She gave me that devilish glare again and said matter-of-factly, "We are following my rules, right? Your phone was not on silent, you broke the rules, and you're done for the night."

During this scolding I hadn't noticed my hand naturally going to my nearly exploded cock and started moving.

"What are you doing? Are you beating off," Ann yelled almost loud enough for someone in the shower to hear.

My hand stayed as still as someone who just triggered a land mine and couldn't move.

"No", I said and eventually, slowly, removed my hand from my cock.

She disgustedly said "You have time to put the cage on before Dillon comes out. Do it!"

I did. It was easier than I thought as I had quickly lost my hard-on thinking about her accusation and possible consequences.

I looked at my text message. Oh great, Harbor Freight is having a fucking sale.

She locked the cage and put the key on the necklace around her neck.

She said she wanted to "spoon and snuggle" and think. Yikes!

Ann was obviously tired from having 6 orgasms in as many days.

We kept this position for what seemed like an eternity as Dillon took the longest shower of his life. Sure.

She said, "I'm too tired tonight to make a judgment as to if you cheated on me with your hand. I will decide tomorrow. If I determine you did, when we fly back to my place tomorrow, I will be with Neil tomorrow night on your final night in town before you fly home the next day."

"Maybe you and Dillon can watch one of his shows while I'm gone."

"We could video chat then."