One of the most popular questions I get when someone writes me on CollarMe is: Will you humiliate me? Often times I tell them I don’t know what they find humiliating. I don’t know them well enough to do that. I know that dil and I had some running joke for a while about whether or not someone would find being stuffed in a closet full of bats humiliating and if so, where was I going to find a closet full of bats? Devin just recently told me that seeing his text messages while he was in chastity on my blog was humiliating. While I kind of hoped he would, I wasn’t counting on it, so was just pleasantly surprised by it. After today, I have a pretty good idea of what humiliates Joey, and that’s shopping with me.
The plan was for him to pick me up after work and to go out. Typically we see each other twice a week. Once during the week and then once on the weekend. This gives him enough time to hang out with his other friends and gives me time to see my other friends and time for Kitty on his days off. Also, the important thing here is that I don’t have a car on the weekends and I get cabin fever if Joey doesn’t come and spring me from the joint. Or at least make my house a little more entertaining for me.
The grand plan? Dinner, sex shop, book store, home. Nothing extravagant. I was expecting that most of our play would take place tomorrow anyhow. For today, I just wanted to get out of the house. Dinner was entertaining because we discussed what sex meant to us and also because I got to watch him suffer through every bite of food he took. A week ago I would have teased him about being a silly boy and not making an appointment with the dentist; this time I could only attempt to sympathize as his appointment had to be rescheduled. Unfortunately for him, I was still entirely too amused by his masochistic tendencies. Smoothies work just as well as real food, right?
The sex shop was where I found myself in all kinds of trouble. Originally we went in looking for stockings. We’d purchased three pairs before and the boy doesn’t know how to take care of his stockings so one pair has a run in it, another pair has a hole in it, and the third pair, well, I don’t remember what happened to them. Since then we’ve acquired some rainbow fishnet stockings (courtesy of yours truly) and possibly another pair but I can’t remember for certain. The point is, the boy can’t have too many stockings. Since it’s buy two pairs, get the third free, I was having a grand time picking out which ones I thought were sexy.
For the past couple of months, I’ve had this recurring dream/fantasy about seeing him in all white lingerie and stockings, bent over something, and being fucked in the ass by my strap-on. I used to have a similar fantasy with my first pet, although it was more of a trashy wedding night sort of setting that he would have never indulged me. Luckily Joey doesn’t mind. I even told him he wouldn’t actually have to marry me, just role play out the honeymoon.
As we were looking at stockings though, I noticed the panties behind us. Now, he has a pair of panties already. Hot pink and black zebra striped panties to be exact. We bought them as a size experiment from Victoria Secrets. Then, I just so happened to find some duct tape in the exact same color and pattern while pretending to be handy in the fix it yourself section of Wal Mart and so had to purchase it. I’ve meant to play with it, but so far I’ve been too busy shoving things up his ass to concern myself with taping his arms together.
At any rate, I found some cute panties, or something, that I thought would fit him. They were black and red, not quite ‘his color’ but they would do…if they fit. Being that they were nearly $20, I thought it would be best if he tried them on first. Of course, in saying that, he just stared at me like I’d lost my damn mind. Luckily he didn’t have to wonder for long, because I made my way over to the sales lady and asked her very quietly, using all the manners I could muster, if it would be okay if a boy used the dressing room, and she immediately shot a glance back to him as he stood there holding the frilly skirt/panties combo and looking like he wanted to die. She lit up! I swear she did. Of course she replied! He just couldn’t take the stockings in. I told her that was fine. We already knew he had sexy legs and they’d work just fine.
While he was trying those on, I found some nice white corsets that would have worked fantastically with my deflowering the virgin fantasy I’d been having, but despite the large size on them, they sure didn’t look like they were a size over small, so I decided to just leave them on the rack. When he came back out, face still red, he admitted that the size was too small. We’ll have to try a different store for his lingerie, but I don’t think it’s going to be a problem. He’s not that big — he’s just not the same size as my usual feminine pets, which means finding the right size is sometimes tricky.
After that, as he carried around his stockings, we made our way back to the actual sex toys. There we were looking at the remote controlled eggs that I thought would be fun to shove in him before we went out to dinner the next time we ate out. I think he agreed, but in that ‘Sure, whatever’ kind of way that he does when there are other people around watching us. None of them were anal specific, but that didn’t really bother me. I just wanted to shove them in his panties, right behind his balls, and buzz away.
Speaking of buzzing, our next stop was at some electro-stim cock ring and nipple clamps and anal plug. I figure the electricity in it wouldn’t be that bad since it was being sold as pretty much a novelty. For whatever reason I thought electricity was more of a hard limit for him, but since he was the one that pointed out the cock straps that went with it, I’m going to go ahead and say no, he’s okay with electricity. Then we browsed the poor, poor selection of hitty toys and almost gave up when I remembered that he wanted a vibrator and I would like a prostate massager for milking him. Lo and behold, I found exactly what I was looking for: a vibrating prostate massager!
As we stood staring at them, I had to decide between whether I wanted him to have a ‘boy toy’, meaning it was black in color, or if I wanted to match the soft purple to the hot pink gloves and stockings that he now had. It was a tough choice, but I figured black would do for this particular toy. There’s enough soft colors in his life because of me. Might as well let him have something black for a change. But the decision was tough, and I insisted he go find something ‘nifty’ for me to look at after I made my decision.
He decided to be the responsible boy and scope the latex-free condoms while I took a short cut through the ‘fetish’ section and happened to notice that the Japanese silk rope happened to come in HIS color! Bright pink! And they had black too, in the event that I needed a second spool. Already my head was swimming with ways to bind his arms with that and the tape and having him wear his panties and his stockings and gloves and all the pictures I could take and how could he not have seen this?! This was totally nifty. I tried to get his attention by sheer will alone but for whatever reason he’s not telepathic. That really cramps my style. So I tried clicking my tongue at him. Still no response. So he left me no choice, and I had to call him from across the store: “Come, puppy!”
Alright, I probably could have used better words, but it worked! I got a long drawn out ‘Wow’ from him, something he does when he can’t believe I’ve done said/done/proposed something, but he came straight to me. The girls in the store noticed too! I’m sure they thought he was adorable. Then I pointed out the rope and told him we should get that next. Meaning I should learn some rope work. I’ve been meaning to for the calendar I want to put together anyhow, but now there’s additional incentive, being that it comes in HIS color.
Finally we were ready. We took all of his stuff to the counter, meaning one pair of stockings and a vibrating prostate massager, and went to check out. I told the clerk how relieved I was that he wouldn’t be stealing one of my vibrators since we’ve found this one and that might have been embarrassing enough, but then I wanted to make sure we got our discount. TNG discount please! But no one ever recognizes that. After a moment or two, she hesitantly mentioned that there might be a discount for a kinky club and I laughed. That would be us. Honestly, if you ever hear someone calling somebody ‘Puppy’ and you see him answer to it, you may as well assume they get that discount and just go ahead and ring it up as such.
In the event that that wasn’t bad enough, Joey got to experience the joy of buying a vibrating toy and how they test it out in front of you. Additionally, I happened to find a huge rainbow colored cock sucker behind the counter that he is so totally getting the next time we’re there. It’s the only cock I’ll ever get to see him suck. And it’s rainbow!
Afterwards, as we left, he mentioned how that was quite the experience. I told him I got points for being very discreet about his cross dressing and he kindly pointed out that immediately after that, all discretion was out the window. Well, what can I say? I tried!

