Day 147

I had a wonderfully humiliating episode today when a stranger saw me wearing women's pants.  It was super embarrassing and exciting at the same time.

I also bought a pair of white cycling shorts today, but having put them on, I don't think I'd be brave enough to wear them in public.  Though they are so tight, I look very small in them.

Day 146

I have returned to wearing the cage.  It wasn't until I slipped it on that I realised how much I'd missed it.  It feels secure.  While the frustration is the same, there's the added security in knowing I can't get completely hard or squeeze myself.

I did feel a little conspicuous in a coffee shop today.  I realised, as I sat in my shorts, that the cage was pretty obvious.  Not as a cage, you understand.  It looked rather like I had a 3.5" erection!  I'm pretty sure the women sitting at the table next to me saw it.

Which makes me realise that when I'm wearing the cage I actually do have a pathetically small penis!  No wonder A suggested I wear it when she humiliates me in front of others.

Speaking of which, I read a great SPH challenge yesterday.  The idea is for a man with a small penis to, somehow, let a woman know about his size restriction.  This, in itself isn't much of a dare but the delicious twist is that the woman has to be someone he works with and dislikes.  The idea being she is the last person in the world he'd want to know for fear of her telling others and, basically, making his life hell.

The challenge I read was accomplished by a guy who set up a few fake email addresses and, by pretending to be a couple of women who also worked in the same company, gradually, let this woman know.  He reported that it was excruciatingly humiliating the next time he saw her at work and since doing it, he suffers every time they're together.

Makes me wish I worked with a woman that I hated!  Then I could get A to let her know.  Much easier than fake emails.

Yesterday I had a ruined orgasm and emptied my balls with no satisfaction.

Day 141

I had a very pleasant conversation with two slightly drunk women on the train last night.  After some light chat about their evening, we started discussing my small penis.  They thought it was ridiculously small when I told them it was 4" hard and 2" soft.  When they left the train, they waggled their little fingers at me.  It was deliciously humiliating.

When I told A, she reckoned they would have been more amused if they'd known I only wished for a smaller penis.

This doesn't look very big now, does it...

Day 138

I see that A has posted a few comments.  It always gives me a special tingle when she does.  I shall try and respond in this post.

In reverse order:

And how did the milking go? - It went very well.  This was a successful milking and it went something like this.  I took my time, pumping slowly until I reached a point where I knew I had to stop.  When I stop, I just let go and my cock bobs around uselessly.  If I manage to stop at the right time, a small dribble of cum seeps out.  I then leave it for a minute so the feeling can subside.  I then start again.  The second (and subsequent) time never takes as long as the first.  I'll try and do this four times and manage to milk a considerable amount of cum without any degree of pleasure.

And this reminds me, how is the publishing coming along? And the second memoir? - I am presently designing a cover for the Cuckold memoir and will publish it as soon as this is complete.  The second memoir is coming along very well.  I'm presently up to around 20,000 words.

I'm going to diarise 26 August. - Excellent!  Though today I was thinking I may have to go longer given that date and what I'll be doing then.  I also toyed with the idea of going 365 days...maybe next time.

You really ought to post a picture of said tight Lycra swimmers. - As you command, so shall I deliver:

I have a bigger tummy bulge!  Then I had a play with a banana:

A also told me she had an orgasm yesterday and made me all excited.

Day 127

Spent a lovely night with A and realised I hadn't blogged for ages.  I wasn't even sure how many days I was up to.  I have rectified this now.

My last milking was Monday June 3 so I'm due for another this coming Monday.  Other than that, nothing much has happened to report.

Day 104

Things were getting a bit rough for the last week.  I was unable to ruin an orgasm and was feeling extremely horny.  It was the most difficult period so far this time.

Yesterday I managed to milk a very big load and it was like a weight had been lifted from my balls.  Of course, it didn't do anything to help release me from the horniness. 

It also didn't help that A sent me an email detailing an extremely hot sex session she had had on Saturday night.

Still, all in all, the first 100 days of this 200 seems to have flown by and has been much easier than my previous 100.  Half way there...

Day 83

On Day 75, I was full of cold but I still managed to ruin an orgasm.  It took longer than usual and it was very difficult maintaining an erection but, eventually, it dribbled out of me.  I felt quite pathetic.  I'm going to be missing my next 14 day ruin so will be looking at 28 days before my next one.

I have finished my Cuckold memoir with some very helpful edits from A.  Hopefully I will be able to publish it on Amazon soon.  I am presently writing my second memoir, tracing my more sub experiences.