Starting Off on a High

Mistress and I have got our fifth year of chastity off to a great… make that, ‘PERFECT’ start, with a very hard orgasm for her and a hard throbbing, unsatisfied cock for me. 

After I had licked her gorgeous pussy to orgasm and worshipped her beautiful feet for a while, Mistress pulled me up the bed and started stroking me until I was fully hard. She soon straddled me and sank down on my rock hard cock, enveloping my shaft with her silky wetness… always feels so good!

Mistress rode my cock for some time, having me beg her to remove her bra and then allowing me to suck and caress her lovely breasts as she squeezed my cock with her pussy. I wondered if she might want me shoot inside her, being as it was our anniversary and all… but I guess it was more fitting to leave me hard and desperate, starting as she means to go on you might say. 

I had intended to ask Mistress how she felt about starting another year of chastity, giving her an opportunity to talk about it, and see if she was still happy with it all and whether she wanted to change anything or stop it altogether. On tonight’s evidence it would seem all is more than well, but a few weeks ago Mistress said something which made me wonder.

She said something about ‘The only downside of chastity is that we can’t just go and have normal sex’. Which I thought we’d long since established we can do, if that’s what she wants to happen. Then the next night we did exactly that, so I guess Mistress came to the very same conclusion. Still it wouldn’t hurt to sit down and talk about it, maybe review our chastity contract and see if there’s anything that needs addressing.

Would You Date a Former Porn Actor?

My absolute favourite TV show right now is called ‘First Dates’, it’s on its third series here in the UK and last night’s episode was a belter. For those who haven’t seen it, or for those who don’t live here and presumably aren’t able to see it, the idea is simple. There’s a nice restaurant in London, where loads of couples who are matched up via the Channel 4 website, meet for the very first time and go on blind dates together. The TV company films it all and shows us the best ones.

It is endlessly entertaining and at times hilariously funny. Last night a guy explained that his mother was half-Egyptian, at which his date looked confused and said ‘I didn’t know you could be Egyptian…’, like Egypt only existed thousands of years ago…? Later she was filmed in the bathroom moaning into her phone that ‘He isn’t even wearing a Rolex’.

But it was another couple who raised the question above. There was a girl and a big guy who had quite a lot of tattoos, and they seemed to be getting on well until he dropped into the conversation that he had made porn films. At which point she pretty much freaked out and disappeared to the bathroom herself. When she returned the situation quickly deteriorated and it was clear that this was not going to go any further.

After the show finished Mistress R asked me if it would bother me, to which I replied that, actually I had never really given it any thought. It’s a long, long time since I was single for one thing… but this got me thinking about this subject and I asked my friend at work for his opinions too. We mulled it over for most of the day, and decided that it would depend on a lot of things, but assuming all things to be equal and that you meet someone who you are attracted to, would it actually be any different from them having slept with loads of people and not getting filmed/paid for it?

In the case of this guy (and, let’s be honest most ‘guys’ in porn) if he hadn’t told her then she probably wouldn’t have known. Of course, other people might tell her, what I meant was it’s not like he was likely to be recognized in the street in the same way that, say Sacha Grey might be. In any case, if he had kept it to himself for a while at least, he might have had a chance to build a relationship with the woman first before revealing something which is obviously potentially quite contentious. True, she’s bound to say ‘Why didn’t you tell me this before… and what else aren’t you telling me?’, but the obvious answer to that is I wanted you to get to know me first, so you wouldn’t judge me unfairly.

Actually, in this instance, the main issue seemed not to be that he’d been filmed and that his porn stardom was an issue or likely embarrassment waiting to happen (funnily enough the woman had worked in a sex shop), but more that she felt like she couldn’t compete with the women he’d slept with because they must be young and have perfect porn bodies…

To be fair, if I was single and a *retired* Bobbi Starr or Ashley Fires wanted me to date them, would I feel secure enough about myself, when all it would take would be ten seconds and a Google search to find video of either of them being thoroughly pleasuredby guys with stupidly big cocks (on the plus side, both of those women have made Femdom / Chastity / Cuckold porn too :)).

Honestly I think it would come down to a lot of factors, not least of which would be their attitude and personality. I certainly don’t think I would dismiss someone out of hand if they told me they had done porn, but I might if I thought it had negatively affected their attitude towards men, and more specifically their attitude towards sex within a normal relationship.

I’m not sure if Mistress R answered her own question or not, if she did I can’t remember what she said. Thankfully it’s not something either of us are likely to have to consider, but it is an interesting question and I would be interested to hear what my readers think?

Saturday's Still on My Mind...

Obviously the events of Saturday have been on my mind for the last few days, how could they not be? So you won’t be surprised that the image of Mistress’s cum covered ass was still vivid in my mind… even as I was licking her delicious pussy tonight and making her cum nice and hard.

Again, as soon as I was on my back and Mistress was stroking my cock, then sucking and slapping it, my thoughts drifted back to Saturday night… being on top of her and slamming my cock into her, getting close enough that I had to warn her, then being told to stroke my cock while she turned over and presented her amazing, sexy ass to me. Looking down at my slippery, wet cock. My hand stroking it steadily, the tip just a few inches from Mistress’s ass, and then hearing her say that she wanted me to cum all over her ass and lick it clean.

I so want to do that again, it was over so quickly. Last time I knew that it was going to happen, this time was a spur of the moment thing (at least as far as I know). On the one hand knowing gave me a chance to relish the moment, on the other, this time was better because it was less… awkward. I loved that after I finished cumming on her, Mistress got up on her knees and presented her ass for me to clean, that was awesome. It was much easier and hotter cleaning her ass like that. I absolutely loved every second of it.

Tonight I didn’t get to cum, but then I didn’t expect to. It’s only been three days. Which isn’t to say I didn’t want to… but no, one more orgasm for Mistress to add to her yearly total was the result. The end of our fourth year of 24/7/365 chastity is approaching, it’s kind of incredible to think about that fact. It’s mildly disappointing that Mistress is going to have less orgasms this year than last, but unless Mistress is going to let me cum an awful lot between now and the 31st (I think not!) then it’s a pretty safe bet to say that my allowance has shrunk significantly this year.

On the one hand I’m pleased about that, on the other I wish I got the chance to cum on Mistress’s ass (and other parts of her gorgeousness) more often… of course there’s always the ruined option. How mean (and hot) would it have been for Mistress to have had me ruin my orgasm onto her ass on Saturday, and then to have had to clean her with my cock still throbbing and desperate to cum properly?

My Last Orgasm This Chastity Year?

Wednesday night was amazing, redeeming my reward led to a wonderful session with some super-hot teasing and anal stimulation leaving me feeling very horny indeed. The last thing I expected was for this evening to be even better, especially since the last few days has been a bit fraught what with one thing and another.

For one thing, Mistress has been having some issues with her car this week, and so we decided to go check out some cars with the idea that she might want to replace her 10 year old Punto with a newer Panda. It was quite good fun test driving the cars and put us in a good mood when we got back. We may have discovered a solution to the problem she’s having, but we are not sure, at least now we feel that we have the information to make a decision if Mistress decides she does want to change her car and trade in her troublesome old model.

Mistress and I have been watching the latest season of The Bachelor (US) on the internet, and again, watching that this afternoon left us feeling very chilled out. We went to bed about 9pm and things began with me lying next to Mistress, gently stroking the insides of her gorgeous thighs until she slowly opened her legs wider to allow me access to her pussy.

I licked my fingers and gently teased her pussy and after a while she pushed me down between her legs. I carefully settled on my front, feeling my hard cock pressing into the bed as I first kissed all around her pussy, before beginning to tease her with my tongue.

Mistress tasted absolutely delicious and I was rewarded with the feeling of her bucking hard against my tongue several times, before she finally pulled away and kissed my head. Then she allowed me to kiss her feet for a while, before having me move up the bed between her thighs.

Mistress grasped my cock and started teasing her pussy with it, before telling me to lick some of the juice off of her lips and then sliding the tip of my cock inside her. She pulled me fully inside her and lifted her legs up onto my shoulders, allowing me to stroke deep inside her, which felt wonderful of course!

Soon I was fucking her quite hard, and we continued like this for a while, since I was feeling very much in control, slowing occasionally to kiss her feet or to watch my cock sliding into Mistress’s beautiful, slick pussy. Mistress was really enjoying herself it seemed and we settled into a fairly brisk rhythm, and before too long I could feel the edge approaching.

I really thought Mistress would tell me to keep going and to shoot inside her, but instead she told me to pull out. “Play with your cock,” she told me as she lifted her leg over and moved onto her side, exposing her awesome ass to me as I gently stroked my slippery, pussy juice coated cock.

“I want to you to stroke your cock until you cum all over my ass.”

I looked down at Mistress’s gorgeous ass and started stroking my cock. Mistress shifted forward a little further, allowing me to see her sexy asshole, as I imagined what it would be like to lick my cum from her ass again. It’s been a hell of a long time since I was allowed to do that, and needless to say it wasn’t long before my rock hard, swollen cock began to erupt strings of cum between Mistress R’s cheeks.

I seemed to keep coming for a long time, depositing a fair amount of cum on Mistress’s ass. As soon as I had recovered my composure, Mistress got onto her knees and instructed me to clean her with my tongue. I moved behind her and eagerly set about licking up every drop of cum, gently probing her ass with my tongue as I swallowed every drop I could find on her skin.

I really didn’t expect tonight to be as good as Wednesday, but incredibly it was even better. And if that was the last orgasm I am to be allowed this chastity year (Apr-Mar), then what a way to finish! 

Redeeming a Reward...

You may remember that I have three outstanding rewards left for my weight loss efforts (though the last week was a bit of a disaster, we won’t talk about that now…). So tonight I thought I would redeem one of these rewards. I was tempted to go with the Oxballs ball stretcher, but I decided instead on the glass anal dildo again.

Firstly though I had to take care of my Mistress’s needs. As we lay together kissing, with my fingers caressing her sweet, wet pussy I wondered if she might want me to repeat last week where I used just my fingers to make her cum for the first time in at least four years…? But as she firmly pushed me down the bed, I realised this was not to be, though I was not in the slightest disappointed as I was eager to taste her delicious pussy.

Mistress had another lovely, hard orgasm and afterwards she lay back while I worshipped her beautiful feet for a while. Then it was my turn and I was soon on my back, kissing Mistress for a while before she slid the dildo into my ass. It felt so fucking good. It really did, and feeling Mistress sucking my cock while she manipulated the dildo with her hand was wonderful.

After a while the lube warmed up and the dildo was moving nice and freely and Mistress decided to climb on top of me, giving me a lovely view of her amazing pussy and ass, before sinking down and taking me inside her as she faced my feet. It was a really tight fit in that position, but it felt great having my cock inside Mistress R’s silky smooth pussy, with the added pleasure of a warm, glass cock in my ass too.

Mistress rode me for a while before lifting off and standing over me, I fucking LOVE it when she does that. I love to reach up and part her cheeks so that I can see her gorgeous little asshole. I love looking at her amazing legs and seeing her swollen pussy right there above me…so fucking sexy!

Mistress had me beg to worship her ass again, which was an unexpected treat and she jerked my cock hard as she allowed me to tongue her delicious, tight asshole two or three times. Needless to say my cock was throbbing hard and then Mistress knelt by my side, working the dildo in my ass as she stroked my cock. By this time I was super-horny and I would have welcomed a bigger toy in my ass, I would have loved her to have slipped her RodeoH’s on and fucked me. I’m pretty sure the dildo was all the way in, but I wanted more (what a shameless ass slut I am!) and by the time she called a halt I couldn’t have been more than a few strokes from cumming….

Hopefully Things Are Back on Track...

There’s not been a lot worth writing about over the last few days, the weekend was pretty shit (Saturday was at any rate…) and the Femdom session on Sunday was quietly forgotten about.

Thankfully, tonight was wonderful. Mistress had a really good orgasm on my tongue, which put a big smile on her face, and indeed, she’s already told me she wants some more attention tomorrow night. 

After that Mistress started playing with my cock and got me really, really hard. It’s hard to believe it’s only a few days since I was allowed to shoot my huge load inside my Mistress’s beautiful pussy (and lick her clean), it feels more like I’ve been denied longer. But this often happens, I find the first few days are harder, rather than easier as you might imagine, and then everything settles down for a while, and then it gets tough around the 35 day mark again.

Mistress was teasing me beautifully, and while she was sucking and slapping my cock I was allowed to tease her ass with my fingertips, this makes it even harder to resist cumming of course, and eventually I begged Mistress to allow me to worship her gorgeous asshole with my tongue. Mistress obliged and quickly straddled my head, stroking my cock hard and fast as I tongued her sexy asshole. She tasted so hot and I nearly came right there, but after a brief pause I was able to continue, until I had to warn Mistress that I was getting close at which point she called a halt.

I was pretty close, and I was half expecting to see my throbbing cock slowly leaking a stream of cum, but it didn’t happen. Instead I just stayed rock hard for about five minutes while Mistress and I cuddled. I can’t tell you how much I wanted to push Mistress onto her back and fuck her hard and fast until I exploded inside her tight, wet pussy… just like last time.

But that was Mistress’s choice… so of course, I didn’t… and Mistress seemed unusually amused by my frustration (which itself is pretty hot of course…) as I casually rubbed my aching, throbbing length against her soft, silky skin.

A Great End to a Tough Week

This last week has been a bit shitty. I’ve had a cold, not so much in the runny nose and coughing sense, more in the kind of feel like I haven’t slept even though I have sense. That, along with Mistress’s period arriving at the start of the week, has meant not much to write about this week.

However, tonight things took a turn for the better. Firstly I got to worship Mistress’s beautiful pussy and made her cum nice and hard, which instantly made me feel better of course. And then after I had made her cum, Mistress pulled me up between her legs and curled her hand around my cock. She stroked me until I was hard and then dragged her nails across my balls to make me even harder.

She pulled me closer and I felt my cock slide easily into her silky, wet pussy. It felt absolutely amazing and I felt so happy to be on top, pushing my hard cock inside her. Despite having not been allowed to cum for 31 days (not even a ruined one) I felt very much in control and was able to fuck my Mistress quite hard and deep.

After a while she turned onto her side, which gave me a perfect view of her wonderful ass. Even so, I still felt surprisingly relaxed and began fucking her harder still. I grabbed her ass and gently pulled her cheeks apart so that I could look at her oh-so-lickable asshole as I pounded my cock into her, and then decided to step it up a gear.

I had a strong suspicion that when the edge came it would be abrupt, I also strongly felt that Mistress was going to tell me to cum when I got there… but, you know, I could have been wrong. On this occasion I was 100% correct, and as I pounded Mistress’s slick, wet pussy hard and fast I felt that (not so) familiar feeling of approaching orgasm. I warned Mistress that I was getting close and she ordered me to cum inside her.

For once, my leg didn’t go into cramp, and I got to enjoy the wonderful feeling of over four weeks of hot cum spurting into my beautiful Mistress’s delicious pussy. Then Mistress ordered me onto my back and she straddled my face, planting her cum filled pussy right over my mouth. She tasted very creamy, and as you can probably imagine I swallowed a fair amount of cum before she got off of me. It was really hot and just what we both needed after a not very fun week.