date night

All posts tagged date night

In case you didn’t know, I’m kind of a control freak so I don’t really like surprises. I like to know what is happening, where we’re going and how we’re getting there. I like to be the one to plan it out all. I’m just not usually capable of handing over that much control without some anxiety.

I do love knowing that cagedmonkey is capable of thinking about me and wants to do something nice for me by taking me out. He’s planned on taking me on a date on tomorrow night but it is a total mystery as to where we’re going. I’m not that anxious about it this time because I know he’s been locked and denied orgasm for 3 weeks and his thoughts are about pleasing me. I know he’s taking me out to do something he knows I’ll enjoy because he’s thinking about me and my enjoyment.

You boys can be very selfish but I’ve noticed it is much less when you are locked and focused on your Lady/Mistress. I’m looking forward to what my sweet boy has planned. Although any precious time we get without the kids is always an amazing time even if we’re just sitting and watching tv. 🙂

On Sunday night, My Lady and I sat down together for a few drinks while watching some TV together. We probably should have prepared a little more for the drunkenness ahead, because in the past these types of “drinking nights” have led to weaknesses in ML’s resolve. In other words… when we get drunk together, we usually end up fucking no matter what the chastity situation is. Sometimes I’m a good boy and I hold back when ML denies me. Sometimes ML needs to feel it and she allows me to cum inside her. We felt that we had some added extra security, knowing that it was ML’s time of the month. Would this time be different? Well…

After a few drinks, kisses, and horny touches, My Lady began to tell me how badly she wanted to have a nice hard cock inside her. I told her I’d be happy to oblige, but I couldn’t unless she released me. At first she shook her head and told me that I should go get the strap on instead, but then she seemed to soften up a bit. She talked about how she really did miss my cock, the hardness of my shaft combined with the softness of my skin. Then I asked her the fateful question of the night…

“Would you be mad if you happened to pass out drunk, if I unlocked myself and fucked you?”

And she thought about it!

This comes back to a post ML wrote about whether or not she wants me to disobey her. We’ve talked about it before, and so I kinda already knew where she stood. But I had to ask anyway.

She responded with a long “Hmmmmm…”

Then she reached behind her neck and took the chain that holds my key off of her neck. I looked at her with a confused and excited face. “If you’re going to do it, I figured I’d start you off. But you gotta get me to drink more first.” She smiled at me. I jumped off the couch and poured her another glass of wine. While I was up, she also told me to get a porn DVD that we got for free with an online sex toy purchase.

WTF??? We’re going to watch porn together? I thought. But there was no way I was going to argue. I popped the DVD in and we started to watch.

We watched the first few scenes, and slowly both of us began to realize something – the movie wasn’t all that great. I mean, yeah, it was porn, so we were both getting horny… but it could have been so much better. The girls were obviously faking it (except for one girl-on-girl scene, one of the chicks was REALLY getting into it, you could tell!), and the guys were not even doing a good job with their dicks. I said casually to ML, “Man, I could fuck you so much better than that and make it look so much better.”

She whispered in my ear, “Oh yeah? Show me.” My eyes shot wide open. I asked if she was sure; she nodded. In an instant, the key was in my hand working on the security screw on my Jailbird. My cock sprang out and was fully hard in seconds.

So much for being locked in the cage 24/7 for two months!

I was ready to fuck her immediately, only one problem – the dreaded cycle. What to do? My Lady had a wonderful suggestion:

“Why don’t you just fuck my ass?”

Well then! Sounds like a plan to me!

I lubed us both up and slowly slid my cock into her tight ass. We both moaned loudly as I sunk in further. I was still wearing the ring of the Jailbird, so my cock was extra full and hard, and she definitely felt the difference. I fucked her ass slowly, making sure not to cum and ruin the ENTIRE chastity plan and start over at square one. But as we went on, the alcohol started to get my head swimming, which pushed my urge to cum at bay. Soon I was fucking her pretty hard in the ass, and she was loving it.

We stopped, and we planned to take a shower together. I stood up and ML went to get the DVD out of the player, which is located on a floor level compartment of our entertainment center. All of a sudden, the animal in me took over and I came up behind her and shoved my cock back into her ass. She moaned and squealed in that sexy “give it to me harder” way, so I did. HARD. FUCKING HARD. I pounder her until her face was pressed into the carpet. I pulled her hair as I thrusted into her. I slammed my cock into her as I spanked her ass and called her my anal fuck slut. And she loved every moment, asking for it harder and deeper. She really is an amazing woman. 🙂

After washing off in the shower together, we staggered into the living room to remove all evidence of our alchohol/porn fueled sex romp (just in case the kids woke up early the next morning, lol). We snuggled in bed together, sans clothes and sans cage. It was wonderful.

The next morning, we got out of bed. ML looks at me and seriously asks me, “Did you fuck my ass last night?”

“Uhhhh, yeah!” I replied. “You don’t…”

She shook her head.

She didn’t remember ANY of it! She remembered the drinking and porn parts, but drew a total blank on the ass fucking!* I told her that was fucking hot, and she smiled a huge smile at me. I put my cage back on before heading downstairs, the two month plan destroyed but the four month plan very much still in play. And I ended up getting something I was craving very badly, but still I’m denied and needing to cum bad.

*Note: when ML reads this post, it will probably be the first time she hears about what happened. I didn’t give her many details when she asked what happened. So, look for her in the comments. She may have some interesting things to say about being my “anal fuck slut” for a night!

Last night  My Lady and I were able to get a babysitter so we could go out to dinner and start up our traditional Date Night once again. We dropped the kids off and headed over to the restaurant that serves the drinks perfectly to ML’s liking – yes, we choose our place to eat on how well the drinks are made.  🙂

In the past, ML and I have gotten somewhat freaky in the car ride to and from dinner (one time, I actually made her squirt all over the floor mat!). I didn’t expect too much craziness tonight, though, due to it being ML’s “time of the month.” We had our normal touchy/squeezy/feely time on the way to dinner, enjoying our time without the kids in the car.

When we got to the restaurant, we were seated in a booth, and ML and I sat on the same side – awwwww, how cute, right? I wouldn’t say “cute” exactly, since ML was planning to touch and tease me throughout dinner! ML had me unlocked for most of today, and she wanted to take full advantage of that PLUS the fact that the kids weren’t around.

After a few drinks, ML was feeling frisky and she told me to take my cock out of my pants so she could stroke me at the table. I sneakily slid my cock through my zipper, and her hand gripped me tightly as she slowly stroked me. I had a difficult time keeping my moans under control as she delicately teased the sensitive spot under my cockhead. I could see ML was enjoying it too, as she was rolling her hips slightly, almost as if she were riding me.

A few more drinks, and ML was certainly having a good time. I was rubbing my hand up her back and down to the waistband of her pants, slipping inside to rub her ass from time to time. Then, inspiration hit me… I slid my hand down further and pushed my middle finger into her asshole. She gasped and then she moaned softly.

“Yeah, do it,” she said. I needed no more encouragement. I began tiny thrusts in and out of her asshole, and soon she began to moan a little louder. It was when she started to bite on her thumb I knew I was making real progress.

“Oh, God, I’m gonna cum…” she whispered. And cum she did! She wasn’t too loud, but it was loud enough for me to hear, and get VERY aroused by. She was grinding down on my hand, cumming pretty hard from just one of my fingers in her ass. After about 20 seconds, she started to come down and regained her composure just before our waitress visited our table. It’s too bad, really… I was hoping to make her order another drink while I was one knuckle deep in her ass. 🙂

Needless to say, we got the check shortly after and bolted for the car. Once inside, My Lady took the opportunity to do something she gets to do very rarely – cum LOUD. We kissed and she rubbed her horny pussy through her pants (period be damned, lol). She was ready to cum very quickly. I slid my hand down between her legs and began rubbing with her, and I whispered in her ear, “Cum, nice and loud for me.”

She totally let loose. Saying she came hard and loud is an understatement. She kept going for a good half minute, moaning louder and louder as waves of pleasure coursed through her entire body. Higher and higher she went, louder and louder she got until she was basically shouting out her orgasm. I absolutely LOVE it when she cums like this. I couldn’t take my eyes off of her. When she holds nothing back, she is so amazing and beautiful. It’s beyond words.

My Lady wasn’t finished even then. On the ride back home, the aftershocks of her massive orgasm kept hitting her, and each one seemed to trigger its own (admittedly smaller) orgasm. My Lady was cumming in the passenger seat next to me as I drove, without even touching herself. She writhed and squirmed in the seat, moaning almost the whole way home. Luckily, she was able to compose herself by the time we picked up the kids. She must have been completely satisfied because she dozed off in the car on the ride home.

It was a fantastic night, except for the fact that I had to go to work following all of this. I would have much rather spent the night with ML – snuggling, kissing, perhaps giving her more orgasms if she wanted them. Instead, I’m stuck at work, once again locked up and denied orgasm. After twelve days of not cumming, I’m patiently waiting for my turn to have a massive orgasm. When it will be is up to My Lady…