Tuesday, 4 October 2016

He spends the day in a g-string for me

Long time no post from me. Life has been interesting to say the least and done quite the number on me. Blogging among many other things has been the least of my priorities unfortunately. As always, I hope that you have been well. It seems surreal that it is already October. One of my favourite questions, where has time flown to! Hahaha! With a lot going on in my life and certain changes coming up. I have been debating whether I should indefinitely take a break from blogging or get rid of my blog altogether. I am leaning towards the former and time will tell. Should I settle on the latter, I will at least see to it that I finish some pending posts such as my relationship with Wall Street Sub and my meeting with CEO Sissy before I take the blog down.

I currently am single, not pursuing anyone nor actively looking. While it would be lovely to have a cultured, intelligent, alpha by day and in public and submissive by night and in private man, there are certain aspects of my life taking precedence. In an interesting turn of events however, SS reappeared in my life.

I thought my eyes were deceiving me when I got a chat message notification from him a while back. I had not heard from him in a while and didn't expect it to. He had sent me a one liner hello message which I forgot to reply to. In the almost three years, he had gone through a major change that I was a bit offended he had not shared with me earlier given that we had been friends, leave alone in a D/s relationship. As I had shared in the post addressing the end of our relationship, we never got around to discussing our feelings, what led to the breakup etc in detail. We skirted around it and since it made us uncomfortable, we avoided it altogether.

I teased him, asking him what he wanted after breaking my heart. And with that question he reminded me of a reason I liked him and Wall Street Sub. Their somewhat naivety and taking everything at face value. He was saddened by this 'revelation' that he had broken my heart and apologised. I could not believe that 3 years later he still could not tell when I was teasing him and chuckled on my side. He did not break my heart. My feelings were a bit hurt but I understood that we realistically could not have continued our relationship. His believing that he broke my heart however paved the way for the conversation we never got to have.

He explained to me that what we had was not sustainable. This I already knew however what pleasantly surprised me was his admission that he had grown to like me and get emotionally attached to me far more than he had intended to and in a manner that he was not quite sure how to handle given that he was married. He admitted that not meeting me was to date one of his biggest regrets however he felt that if he had met me, the feelings would have just intensified and made it harder for me. He realised that this was a case of careful what you wished for lest you actually get it and don't know what to do with it. I was grateful that even though it came 3 years later, we got to have the conversation.

We agreed to be friends. We chatted on and off for a few months. I shared with him an incredibly intimate challenge I am currently facing and he has been nothing but supportive. Our fondness for each other returned and with it, we fondly relived moments of our D/s relationship. He admitted that he had frequently looked back at our chastity contract. What was an innocent trip down the memory lane resulted in him sharing two Fridays ago that he had not orgasmed in almost a week. He came on chat just as I was basking in the afterglow of an orgasm courtesy of an afternoon masturbation session which I naughtily shared with him. He revealed that knowing this had him leaking at his desk at work, wanting to desperately orgasm. I told him to compose himself. I innocently told him that he didn't need to orgasm anyway since I had done it for both of us. He asked if I was controlling his orgasms again and I teasingly told him maybe I was. 

Again, his taking everything at face value can be rather humurous. My tease resulted in me telling him that he was not to orgasm all weekend. He agreed to it. In fact I decided on a week. I was testing to see if he was serious and he believed me. So much so that it turned into he was not going to orgasm for three weeks in total. I still had it in me. The right words and like putty I toyed with him. This was all meant to be innocent. I was not looking to rekindle our relationship and I certainly had no interest in one but I was enjoying what was happening.

Confused, he asked me whether that meant I owned his cock again and my reply was I was not sure but I wanted him to do it for me. He agreed to, because I wanted him to do it for me and nothing brought greater pleasure to him than pleasing me. To my delight, I found myself excited by the prospect once again. And with that, I mercilessly teased him. Reminding him that I was laying naked in bed, my wetness from my orgasm between my thighs, debating whether I should play with myself again while he was at work and could do absolutely nothing about it. Suffice to say, he was a tortured dripping mess, wanting to so badly play with his cock and orgasm then and there. 

I decided to further test him and ramp up the teasing. You would think that I would have mercy on him but I was not having any of it. I was not sure whether he would go through with it but he did, an even more pleasant surprise! I remembered that he had a suitcase that contained his kinky toys. I asked whether he still had it and he admitted that he did. I asked the contents of it. Chastity cages of course, butt plugs, dildos, lube. I asked what more was in there. He finally said wanted I was after. A garter and some panties. 

"I want you to put on a pair of panties to work on Monday," I boldly told him. 

I honestly didn't think he would. We had never explored this, even though on his blog he often reblogged images of men in women's underwear, while caged and while not. He agreed to it and admitted that the idea had him a complete mess, incredibly turned on. I asked for pictures, a few of him in his panties with his chastity cage on and without his chastity cage on but while erect, his erection being visible through the panties. He complied. I blame CEO Sissy for getting me excited about the prospect of seeing a man in female underwear. The pictures arrived on Monday as requested. His caged cock looked lovely in the black and grey panties with a tiny pink bow at the front. His free erect cock looked even lovelier in them. It was my turn to be a drippy mess. I didn't have to tease much, just being in the panties had him in a dangerous state of arousal all day.

Following the success of the day, I asked him what other panties he had. And his reply was that all he had was a couple of g-strings. And with that a delicious idea crept into my mind but would he actually comply? It surely was going to be uncomfortable but I wanted to see if he would do it.

I sneakily granted him 3 strokes of what I had now claimed as my cock yet again and he was not allowed to play with without my permission. He frantically stroked and said he was so desperate for more. Aaah, the perfect opportunity for him to walk right into my trap. I told him he could have 7 extra strokes but if he did, he would have to spend the following day in a g-string. I thought he would draw the line at that but was again surprised when he said that he wanted to take the extra 7 strokes and spend the day in a g-string because he knew it would please me. By now you should know that he was a dripping mess. The powers of orgasm denial! It had only been a week and he still had 2 more to go. To what lengths would he go in future? I am open to any kinky ideas!

I asked him to send me a report of his day in a g-string. Given that he is now 6 hours ahead of me, by the time I was getting up, he would have long got into his day and gone through the motions of being in a g-string at work, giving him material for his report. Besides, he is a brilliant writer and I always enjoyed his written reports of his days in chastity for me when we were in a relationship. I wanted to understand what the experience was like for him.

Below is his report. Humourous, well written, insightful and arousing to me as always.

Dear LD,

Last night I was given a choice, and as usual, I didn't really think it through. Go to sleep with three strokes of your cock, or get the privilege of seven extra strokes with the proviso that I wear a G-String today. I jumped at the 7 extra strokes, but any pleasure was short lived, and I had a tough time falling asleep, trying to NOT think about stuff that makes me horny (and also trying to not hump the mattress).

A deal is a deal, and so I got the G-String out of the suitcase this morning. It's not a sexy, silky G-String - something from China that looks like it was made on a budget. Blue and green. I waited until I got to work to put it on, and had a chuckle at how ridiculous I looked. G-Strings are clearly not designed for people with cocks (well, at least this one wasn't). I was more out than in, and the string part didn't do a very good job of dividing my balls. Also, I was quite aware of the string as it went round the back - all tingly and sensitive.

Once I had put my trousers back on, I almost felt more naked than if I wasn't wearing any underwear. It was odd - this strange sensation that people can tell. Like they could see something was different. And oddly enough - that turned me on. Almost from the moment that I put the G-String on, I've been continuously dripping. I suspect partly because of the perviness of wearing women's underwear, and partly because I haven't cum in over a week now.

Work has been tricky today - I haven't been able to focus - my mind keeps wondering off. Not with dirty thoughts, but about the secret in my pants. And then there is the awkwardness when talking to female colleagues. It almost feels like they know. It must just be in my head, but it feels like they are giving me some sort of knowing look, like I'm one of the group now. I feel quite self aware.

I also find myself checking for wet patches, as it feels I must have leaked litres over the course of the day.

I quite like the feeling of the G-String over my anus area - and I have caught myself more than once rocking back and forward on my chair - sort of like grinding on the string bit. Also, when I walk about, there is quite a bit of movement of the G-String, both over my anus, as well as my balls and *your* cock. The result is that I have been sexually aroused for most of the day - either sitting still and trying to think happy thoughts, or walking about trying to ignore the sensations in my crotch area.

Obviously, all this makes me think about you. And to tie in with something you said last night. That you wouldn't have sex with me. At first I thought I would be offended by that, but the reality is that I am not. It doesn't feel like our relationship ever had that as an option. I'm not your sexual partner, and I don't crave sex from you. I crave your attention, and your control. I enjoy being your "plaything". I enjoy hearing about your antics. I enjoy trying to make you laugh. But I can't actually picture myself having sex with you. I don't think I am worthy of that. (Right now, you'd just have to look at me in a sexy way and I think I would cum!)

(Enough spilling my thoughts!)

Back to the report.

I wonder what it would be like to go further. To be riskier. Would I be as turned on? And why am I so turned on? Do I like dressing like a woman? Or do I like the element of danger? Or is it because I am doing something you asked me to do?

Given the choice of 3 strokes of your cock and sleep or 10 strokes and wearing a G-String again, what would I do? (I just coughed, and a huge gooey drip escaped from your cock!) Take the lack of contact and touching, or go with the heightened arousal, risk of being caught, and general horniness? Both have their upsides and their downsides. But I think we both know what I would choose. And we both know that I didn't choose the extra 7 strokes of your cock - I chose the option of wearing a G-String!

Thank you for this highly entertaining day - it's been quite a roller coaster with lots of bad thoughts, good thoughts, introspection, and a gooey mess!

SS

We are not pursuing anything seriously at the moment and never will. I am simply enjoying him as a friend and "plaything". He made it to 2 weeks without an orgasm today. One more week to go. His longest record was 45 days. I am tempted to propose that we try and see whether he can beat it. 7 weeks perhaps? * I hope he does not still read my blog. I wouldn't want to ruin the surprise. He really should have followed his own realisation. Careful what you wish for lest you actually get it. *wicked grin*

5 comments:

  1. I hate to hear that you may be ending your blog. I found your blog late but I always enjoy reading your words.

    Also just writing to let you know yhat I enjoyed reading this post and to wish you a good day.

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  2. Like Miss Lily, I have recently discovered your blog. I've enjoyed reading your thoughts and ideas for submissives. Thank you for sharing them. I do hope you decide to continue writing.

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  3. Thank you for sharing LD.

    I would be bummed if you shut down your blog.

    I hope you are doing well.

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  4. hot...............

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