A Risky Return to Sin City

We are off again. DR. D is yet again cleaning me off with antiseptic wipes, leaving the ball strap in place but removing the gag, giving me a drink, collecting my pee and straightening up the van. Are we not going to the house yet? I ponder to myself. This is not at all what I expected. On the other hand, being bound and then sexually assaulted by people I can’t stop and don’t know is exactly the substance of my primary fantasy. DR. D knows it. He’s giving me exactly what I asked for in a unique and creative way, still I’m unsettled about it as it plays out.

Again, a quiet phone call, a short drive and we arrived. From what I can see looking out the front windshield we have left the business districts of Vegas, and we are now in a residential area. We pulled into a driveway and stopped. The boys open the side door, and DR. D steps out, leaving the door open. He’s gone a few minutes and returns with a friend. As she climbs in, she says “Hi Sweety, it’s so good to see you again. Looks like you’ve got yourself in another fix.” I immediately recognize her as the trans Dominant ‘Mistress’ that teased, abused and fucked me the last time I was here. She caused me the most mental angst on that trip as she, while packing a penis, is a beautiful and sexy dominant vixen that excited me and therefore threatened my line on sexually interacting with women. I wasn’t expecting her to be here. “DR. D said you couldn’t wait to suck my cock, and I can’t wait to fuck that tight ass of yours” she remarked in her very high sexy voice.

“Oh, look there, isn’t your ball sack all cute and sexy with its little leather strap. It makes your jewels look so delicious. Now, let’s get you ready.” And she begins to flog me. My back, my sides, my thighs, my butt and then my balls, especially my balls and penis. She is skilled and so I received my first real sustained whipping torment session of the night. The flogging goes on for a long eight to ten minutes as she verbally teases me while she moves about. And then she is in front of me. “Open, Sweety and show how you love my cock,” she enthusiastically states. In she goes and she is not covered. She wasn’t the last time either. She is on DR. D’s health approval list. Someone that he knows through both the circle of people they play with and actual medical testing, are known to be reasonably safe to have unprotected sex. In case you didn’t read my last journal, DR. D is a real MD. It is one of the reasons I ‘trust’ him, he does keep me medically safe.

I attempt my best efforts of this evening to suck her. She’s been good to me in the past. Not having my hands of course makes me less effective, but I use my tongue, lips and what little head movement I have. She does her part too, slowly moving her rigid dick in and out while moving my head with her hands. Her moans indicate we are making a good team. Already I start having troubling thoughts as this is arousing me sexually and I know it’s because she is as close to interacting with a woman who is not my wife, maybe too close, as I can get. I know she is a male, that there is a real functioning penis between her legs, but… She takes her time and enjoys the moment. When she has as much gratification she can handle without cumming, she extracts herself and then move to my butt.

“OK Sweety, I know this is why you flew all the way out here. You wanted me to fuck your bound tight little hole. I’m going to make love to it like no one else can.” She starts with a gentle finger penetration. With ample lube I am digitally violated for a good five minutes. My prostate was massaged. From it, I could feel my own cock grow. As said, she is good at her craft. And as my cock grows so does my guilt. She reaches under with her free hand and provides an awesome hand job of my now erect cock.

She is now done with her hand work. With her erect penis, she drives its full length into me in one swift motion. She reached far under me seeking out my nipples which are pressed against the platform on which my stomach and chest are bound. She wiggles her small hands in and squeezes my nipples as she establishes a slow but steady rhythm of thrusts into my rectum. She takes her time, taking full advantage of my undefendable availability. And I do my part, pushing back, squeezing my rectal muscles and then relaxing. All that I was taught.

I have described her in my previous writing. As I have alluded to, she is hot. Dress as a Dominant Mistress in black leather, she is the spitting image of the character Tiffany Chester, also a dominatrix on the cable TV series ‘Bonding’, played by Zoe Levin, who is a 5’5” slender, champagne glass busted, very attractive actress. They could be twins. And excitingly, just my type. Without the penis, it would almost be impossible to distinguisher her from a woman. And I am racked with guilt and deserving of punishment as I participate more than ‘just taking it’. I know DR. D is watching. I know he set it up. I know I am being turned on. I know this is his devious plan. I know he will get his kicks punishing me for it, knowing that I will accept that it is justified. He’s the devel at times. BDSM is his thing, pushing subs to their limits his pleasure and specialty.

She must have fucked me for a good thirty minutes. I have no idea how she can last that long, I surely can’t. She seemed to have enjoyed it all and was not simply roleplaying with me. What I know is she coated my insides with a large load of cum. I no longer have a cream free hole. “You do your best to keep me inside you all night, it will make you sleep better knowing I am still with you,” she says as she withdraws. Knowing it is there will help support the guilt, not make me sleep better.

She spends a few minutes gently rubbing my back and butt as she casually chats with the boys. Eventually, the chatting comes to an end, she comes to my face and tenderly kisses my cheek and departs.