Toy Chest

Pete was one of my regulars. He was a bit short and squat (which Mama don’t hate) with dark hair. I’ve never been good at pinpointing ethnicities, but he was something swarthy – Italian? Middle Eastern?

He worked with models, which is something that either a lot of guys who use hookers do or a lot of guys who use hookers claim to do. It kind of makes sense though; the mindset of commodifying beauty is the same, although Kate Moss’s face goes for a LOT more than my ass.

Anyway, I liked Pete. He was a nice guy with a sense of fun in the b-room, who was looking for a playmate more than anything. I generally just walked in, stripped down, and spent an hour rolling around with him on his king-size bed. As part of my continuing education on the various neighborhoods of New York, he lived on Wall Street, which is a weird part of town to come to at night because there’s literally nothing happening. I guess that’s why guys like Pete outsource their own entertainment. I saw him about once a week, and he was understanding about the scheduling conflicts of my class schedule and part-time job. I often went straight from my Thursday night class to his house, leaving me with the age-old debate: is it better to hook casual or learn trampy?

After a few weeks, Pete started to ask me what kind of toys I had. Since we were naked when he asked, I figured he didn't mean Slinkies and Silly Putty. At that point, my naughty toy collection consisted mostly of an aquamarine glittery vibrator and a red buttplug I’d gotten for free. The next email I received from him after this conversation read:

Can you pick up another buttplug (so we can both use them), some lube and a strap-on today, and then come over later tonight? I will pay for them. I am so turned on just thinking about it.

Well, HELLO!

My experience with the buttplug had been limited so far to admiring its cherry red color and feeling contentedly slutty for its existence in my night stand. I wasn’t at all sure I wanted the thing actually, you know, plugging my butt. I had used a strap-on once before, but it was with a girl and I was on the receiving end and the hotness of the experience was hindered by the fact that it kept slipping around and she had to keep one hand on it to hold it in place while she fucked me with it.

But when duty calls, callgirls rise to the occasion. And yes, I’m resisting the disgusting “duty” joke here. I decided one adventure was enough for a session, so I picked up another buttplug and tucked both of them with a vial of lube into my book bag next to my Anthropology textbook.

When I showed up at his pad after class, we immediately unwrapped my bounty (which had that gross, “new sex toy” smell). Once we got our clothes off and made out for awhile, Pete started out rubbing the lube into my asshole and pressing the little red rocket against my rosebud. I’ve trained my asshole to be suspicious of strangers, and it immediately clenched up against the intruder. With slow and careful prodding, he managed to work the tip of the plug inside. I had my doubts about it going any further, but slowly and surely he worked it up there until just the round base was visible.

I’m going to assume that everyone reading this has had SOMETHING up his or her butt, even if just the usual thing. So you are all at least passingly aware of the feeling of a stretched asshole. Once you get used to it, it just feels…kind of weird. Not good or bad really. Just different. And psychologically there’s something quite pleasingly dirty about it.

Once I was satisfactorily plugged, we moved on to the (bigger) buttplug reserved for Pete’s use. His browneye didn’t require the same finessing that mine had; I pretty much just popped that sucker in there and wiggled it around a little. As I moved my head closer to inspect my handiwork, I became very grateful for the piece of plastic between my hand and his ass. He totally had dingleberries.

That pretty much put an end to the ass play for me, and I guided him into less ass-related waters. He tried to use my freshly loosened butthole as a segue into anal, but it wasn’t for sale, so we ended up doing it regular-style with the buttplugs in.

I still have the red rectum raider but I don’t think I’ve used it since (I did wash it though, promise).