Princess Call: How Princess Popped My Cherry

Well it took Her long enough! sheesh! I've been strutting around like some sort of tart for weeks now. Presenting my wanty needy bottom like some sort of dirty girl whenever Princess and I crossed paths. We had a stretch of bad luck and if you don't care to read about that scroll down to Prom Night and you can read what happened with me getting my cherry popped.

Back Story (pun intended)

Princess Grace has been yakking about this Aneros thing off and on in Her Tease Times (10PM EST Thursdays) for about as long as I had the pleasure of knowing Her. I've never dabbled in toys, never used lubes, I guess you could call me BoringBillyBear when it comes to that. Most of what I need is comfortably roosted in my head, which I usually have near by and means I don't need a lot of equipment to play.

Still billybear was intrigued. I believe I let this slip in a phone call with Princess and She pounced on that like a kitten on catnip giving me home work down the lines of acquiring one. There are certain harsh realities that I must operate under that made this a not so simple task. But as we all know and desire to make happen, what Princess wants, Princess gets.

Before the January 11th TeaseTime I had located one and my purchasing of the thing is a story in and of itself, let's just leave it at the fact that I had some fun with a cute little clerk (which was surprising in and of itself but this place was fairly upscale) named "Lacey" asking questions like, "and this will make me cum really, really hard?"

Lacey was far tougher to fluster than my dearest and closest friend in the world, Panty Princess Jessica. Lacey also knew what she was doing, suggesting an appropriate lube since I was unwilling to shell out $125 for a jug of Eros Lube that Princess recommends (they didn't have a smaller size). They had like five of the Aneros models and I decided that the Aneros MGX would be the best "fit" for me, kind of a beginner model I guess.

So I waited and dropped my Aneros bombshell on Princess during that January 11th TeaseTime. I think it was the only time that I flustered Her, which was nice. I think Princess realizes that it may take me awhile but I will do what I say I'm going to do. I'm not just a talker. I respect Her too much in that regard, if I'm on my cell and She's having me whack off in traffic then that is exactly what I'm doing. Thank God I don't own a cell (soft smile). My point being if She asks me to do something and I tell Her I'm doing it, well I really am doing it. That's why I tend to shy away from Her, "You'll do anything I want?" queries in TeaseTimes. That's a very dangerous question from Princess if you're really a player!

This Aneros business was important to both of us. She likes to play with this toy (a lot more on this later) and since I've never "gone there" with an anal toy I was determined that this Lady would be the one to claim my cherry.

Well bad luck after worse luck occurred. I had a series of RealWorld events, Princess got sick. We couldn't hook up. Suddenly I went about fourteen days without cumming (this just sort of happened, Princess has issued a "license to cum" for me since denial is a very dangerous game with billybear.) Anyway it just sort of happened. All the while that evil Aneros was in the back of my head whispering plaaaay with me, Princess will never know, come on. And I was thinking about Princess Grace and even though I hadn't been able to converse with Her nearly as much as usual (both of us being swamped) I had the impression that sharing this experience with me was important to Her. I knew it was important to me.

The incessant drone of the Aneros whispers faded into the background as the want and need of having MsGrace "do me" took over. It became a primary focal point for me. This was to be "our" experience, and only ours, other then the fact that I'm spilling details here (LOL) but not all of them just the experience of the Aneros. Finally the stars realigned and I was able to place my call!

Prom Night

What to wear? What to wear?! I finally decided to pass on the tux and went for a strapless pink prom dress since I was most definitely the girl tonight. I lit scented candles, put Possession on and started drinking. Princess likes her virgins tipsy, not drunk, that comes later.

Sooooo ...

First and foremost this was one incredible, awesome call on every level, across the board, just fantastic! So let's begin.

MsGrace was very aware of my nervousness on this. She knew exactly how to play me. We chatted for a few minutes and then She asked me if I had "it" nearby.

In case you don't know much about this device (I didn't and once acquiring it I kept myself deliberately in the dark about it, wanting to experience every aspect of it through Her) I was under the impression that it was made of latex from its pictures. Nope. It is hard as a rock. That intimidated me a bit particularly with those dangly jobbies coming out of the bottom. Billybear does his calls sitting up. I IMd Princess about this and she told me "it can be done but you have to be careful." Well I decided to do this lying down, I'll do advanced positions later if needed.

She tells me to stand up and coat the thing with lube, but don't make it all "gloopy." Gloopy is a technical term meaning "don't use too much."

"OK, it's coated but not gloopy"

"OK, insert it gently, relax 'down there' and press it in slowly"

This was an interesting sensation for billybear. It went in about halfway and then after getting it over the hump slid easily in. It also goes in a certain way. The device is bent and you want the bent end towards the penis. After it was in She told me to clinch (clinch will be my technical term for 'contracting the sphincter' since the word 'sphincter' grosses me out for some reason).

Princess asks me how it feels and I'm drawing a blank on the description and tell Her something down the lines of, "Well I'm definitely aware of it." Which drew a giggle. She tells me to sit down slowly and carefully. Billybear sat down slowly and oh so carefully. And then she tells me to lay down and I do on my back. Her tone and attitude is so sweet and gentle. That reads silly in a way but it was exactly what I needed. Reassuring.

Her cock is harder than the fucking Aneros. I'm continuing to clinch and relax and She's telling me that I should be noticing somethings. What I'm noticing is that Her cock is a leaky mess, precum just oozing out and that my mind is an equally deviant mess. I'm not exactly in the mood to chat about the weather at the moment I want to talk about very naughty things. Princess is aware of these effects and She's weaving one of my absolute favorite fantasies into Her instructions.

I am immediately and completely "subbie" at this point in time. Just clinching and relaxing and listening and participating to the best of billybear's abilities. Normally in our phone calls I'm no where near as subbie as I am at this point in time. I'd guess we're maybe five or ten minutes into the call.

On one of the clinches Her cock suddenly coughs up a pretty good blob of precum mixed with cum on my tummy. It says something like, "Bleagh, uh, sorry, I over ate, I feel a little better now."

I relay this information to MsGrace and She tells me to lay off the clinching for a bit, that this device can be used for milking (which is not our objective for tonight) and that we have to be cautious because I've been in denial for awhile. She tells me to roll onto my side.

Now before I get into the rest of this She made one more observation at this point in time. She said with Aneros play most of Her pets get very vocal. Loud. But naturally Her billybear is different (of course - why be normal? - lol). The more turned on I get the quieter I get. During this call I was very quiet but I was trying very hard to give Her the feedback She deserved. So, in a nutshell if you're a screamer, you're most likely going to be a louder screamer.

So I'm on my side and She tells me to reach back with my hand and grab the little curly queue thing that's at the back of the Aneros. I do so, then She tells me to move it front to back, front to back. Her voice was very rhythmic and soft. Then She said side to side, side to side. She would very the pattern, I preferred the front to back (which puts the device into more contact with the prostate) over the side to side but believe you me, it was all good. While She's doing the pattern thing She's also weaving in the fantasy and working the instructions into the fantasy. I am astounded I'm recalling any of this to this level because I was soooo gone, soooo completely into Her.

I have yet to touch Her leaky dibbly cock. It's starting to complain down the lines of, "Oh I know it's all about the ass tonight but come on, toss me a bone, give me a little shake dammit!"

I've said nothing to Princess about this little whiner but being the absolute best She knows and weaves permission into the fantasy. In my little fantasies it's always Princess touching me. The skill and depth of knowledge on display by Her during this entire call is beyond impressive. I hope I'm giving you an idea of it. Her ability to work how to use the Aneros and keep it working within the fantasy was fantastic. Once She started the fantasy was never broken by just instructions.

I am very, very deep and She's speaking softly, wuving Her billybear, deep inside me in every sense of the word. I'm on my back, my eyes closed, listening intently to every word, trying to provide feedback, not sure if I am but trying hard. Wuving Her right back.

She's coaxing me to cum now. Gently, taking Her time but building it up. Her cock is unimaginably hard at this point in time. I don't think it's ever been harder. I'm getting to the moment of going over and I'm subconsciously clinching at this point. I'm not trying to fight it at all but I am trying to preserve that moment in time when you actually do go over. You know what I mean I think, that one moment when you know the next stroke or dirty thought or trigger from Princess will "do it" and your orgasm will begin. For me the Aneros helped stretch that moment, I don't know if that's true "real time" but it's true "in my head time."

I literally feel my eyes roll back into my head and Her cock goes off like a rifle! I know this because the spasm of Her cock, the cinching, the "trigger" and everything else lined up just right and a huge wad of cum splashes against my chin! Like from a squirt gun. I am not kidding. Sheesh!

This unexpected event jars me a little bit and I'm cautiously opening my eyes to get an update. My Princess is saying something, encouraging and calming words I think. I've been reduced to some primal state, I can hear Her in the background but I'm not really listening or understanding. The splash of sperm has caused me to snap Her cock into an upright position. Normally I'm more of a dribbler but in this case Her cock is proud and hard and and cum is flowing out of the head with littler eruptions shooting up. Her little Vesuvius.

The orgasm rolls on but Her cock is loosing steam turning more into the Wicked Witch of the West, "I'm shrinking, what a wicked world ... what a wicked world" while still spasming and cumming. I'm starting to understand what MsGrace is saying now. She's calming me, telling me to breath slowly, calm down. I have no idea what She heard from me, what I said or moaned or anything. I'm pretty sure She heard me though because as I was starting to come to my senses She was right there with me. Her timing perfect! So I think I was giving back.

I'm figuratively laying with my head on Her lap at this point. Relaxing, listening to Her, calming down, heart rate slowing. Spent.

The Aneros is starting to bug me a little and I ask Her if I can take it out. She says sure, roll on your side and gently pull it out. Well my ass seems to have fallen deeply in love with the Aneros and wasn't real willing to "let go" with out a bit of a fight, it clung tightly to it's lover as it was withdrawn. I think it still misses it :-)

We chatted for a bit. I was glad I brought a towel because I was a real cummy mess! And the Aneros will get "dirty" and it's very easy to clean.

It was an incredibly intense, long orgasm. I know that the Anerose helped with that but would have been not nearly as intense or enjoyable or long without the presence of my Mistress, my Princess Grace. This entire unbelievable, erotic, fun experience I gratefully lay at Her feet.

So if you're thinking of playing with this device or even have in the past I can guaran-fucking-tee you that your experience will be oh so much better under the guidance of Princess Grace.

Billybear turns his trusting eyes to his Mistress. Princess Grace words fail me. You know what you mean to me. You know what this meant to me, You were there. Wuv You and Thank You so very much!

Your pet, Your billybear

PS: Princess you should consider making an Aneros type mp3 (but purchase stock in the company first, billybear expects there will be an uptick).