Hooker Strap

Paying a hooker to fuck you with a strapon. Sounds insane right? I'll admit it sounds crazy, but when a man is desperate he'll do anything, and I'm desperate. For years I've read strapon erotica, masturbated to strapon pictures and videos, and even fucked myself with various dildos. I've got a small collection in my bedside drawer. The small vibrator which buzzes my insides nicely, the large lifelike penis replica which fills me up, and then the gargantuan cock which I can barely get inside myself at all. There's a few more in there that I use from time to time; suffice it to say I'm into strapons and anal sex.

I'm a member of two different strapon sex paysites, which is how I get my internet fix for pictures and videos. I usually log on every day, sometimes twice a day, and I masturbate myself while watching some other schmuck get his ass pounded by a beautiful dominating mistress. Did I mention that I'm really into a dominant chick fucking me in the ass? Yeah, the fucking is one thing, but it's not really complete unless it's a chick talking down to me and slapping my ass and spitting on me, etc (in the fantasy at least). I've never actually experienced strapon sex with a real woman, which leads me to my current situation.

I logged on to Eros Escorts and picked out a beautiful blonde chick who claims to be a dominant gal who loves to entertain her dates. Of course, there's no mention of sex, but who would pay that much money just to have dinner with a chick (over $1000). Her name is Eden, and she stands at 5'11" tall with just 120 lbs on her slim frame. She sports a pair of 34C breasts and a finely shaped ass. The website featured lots of pictures of her in very sexy black vinyl clothing, which is also part of the fantasy. I like the shininess of the vinyl and the sound it makes as it strains against someone's body.

I think it's pretty rare when someone gets to live out an honest to god fantasy, and today was my day. I had an appointment at Eden's place at 6:00 to get my strapon fucking. I didn't have to do much when I called, I simply gave her my name and let her know what I was looking for. She sounded quite sensual on the phone, a well practiced manner I'm sure. I threw on a pair of jeans and a polo shirt before heading over to her place, which turned out to be a fairly nice looking two story house.

I knocked on the front door and was quickly greeted by a beautiful blonde (just like the picture) in a black silk robe.

"Welcome Robert, are you ready for your appointment?"

"Yes Mistress." She had instructed me over the phone that I was to address her as mistress.

"Good, come in please. I have prepared a drink for you, white wine as you mentioned on the phone. Why don't we sit down on the couch and talk for a bit before we get started."

"Yes Mistress."

Eden brought the two glasses of wine over to the couch and gestured to one of the cushions, pointing to where I should sit. I took one of the glasses from her hand and got comfortable.

"Tell me Robert, what do you do for a living?"

"I'm a systems engineer at a large consulting company. It's fairly mindless work, but I enjoy it nonetheless. The pay's quite good and I get six weeks of vacation a year." I took a sip of my wine. "How long have you been doing this?" I said as I gestured around the room with my hand.

"I've been an escort for three years now. I started after my husband cheated on me with his secretary and I was left with nothing. We were only married for 4 years and he hired a good divorce lawyer. I love sex and I enjoy socializing, so this seemed like the perfect job for me."

Eden's silky robe had parted slightly when she had sat down on the couch, and I was trying hard not to fixate on the partially exposed breast flesh that was currently on display.

"You're beautiful Mistress, this couldn't have worked out better."

"Why thank you Robert, you're sweet." She stood up off the couch. "I'm going to go change now. Why don't you stay here and enjoy your wine. I'll call you in when I've finished changing and we can get started."

She leaned down and planted a kiss on my cheek before running her hand down to my crotch, giving my cock a quick squeeze, and walking away.

I don't drink much, so by the time Mistress called me into the bedroom, my head was slightly buzzed, a perfect condition given what I was about to do. I hoisted myself off of the couch and headed down the hall towards Mistress' voice.

The door was open a crack already and a gently pushed it all the way open with my hand, revealing a fantastical site.

Mistress Eden was standing in the middle of a darkened bedroom. Against one wall was an elegant looking wooden framed bed. There were equally elegant matching dresser pieces in the room as well. The walls were painted a muted beige color, which worked perfectly with the rest of the decor. However, the main attraction of the room was the beautiful lady in leather standing in the middle.

Mistress Eden had changed into the outfit I had described to her when we talked on the phone. Starting from the bottom she wore a pair of black vinyl boots that ended just before her knees. Under those she had on lacy black stockings which came to mid thigh. The stockings were held up by a black vinyl garter, under which sat a pair of sexy vinyl thong panties. To top it off she was wearing a painfully sexy vinyl tank top, which fit her upper body like a glove. Her pert, sizable breasts were well accentuated by the top and her stomach looked amazing. The last touch to the outfit was a pair of vinyl gloves that went all the way up to her upper arm.

Sitting on the bed was a strapon cock, black and 8" in length. I took the whole scene in very quickly and found my cock stirring from excitement. Everything was just as I had imagined it.

"Robert, I want you to strip for me. Leave nothing on."

"Yes Mistress."

I quickly stripped my clothes off, with my boxers being the last item to hit the floor. I piled my clothes in a heap in the corner and stood there naked, waiting for my next instructions.

"Come to me my little slut. I want you to get on your knees in front of me."

I followed her instructions and was soon face to face with her crotch.

"Kiss my pussy, lick me right here" she said pointing to her vinyl covered pubic area.

I ran my tongue over the vinyl underwear, attempting to lick the spot where her clit was most likely to be. The material tasted interesting and I could smell her pungent pussy even with the vinyl barrier.

"That's a good boy. Lick my pussy you little slut. Lick it good."

Mistress Eden threw her head back and moaned. Then she grabbed my hair and pulled me away from her crotch. She reached over to the bed and took hold of the strapon harness, giving it to me.

"I want you to help me get into this."

I was momentarily transfixed by the harness, salivating slightly at the cock, conjuring imagery of it fucking my asshole in my head.

"Don't worry slut, I'll be fucking you with it soon enough."

I helped Mistress into the harness, sliding it up her legs and buckling it tight on the sides. I returned to my knees, only this time instead of her vinyl covered pussy at my face it was a cock. I simply stared at it, unable to tear my eyes away from the vision of my fantasy.

Mistress Eden stroked the cock slowly, starting at the tip and running her hand all the way down to the base. It was incredibly erotic and I was suitably turned on, my cock standing at attention now. Mistress put her other hand on the back of my head and brought it forward, pulling me towards her cock.

"Kiss it for me Robert. Kiss my cock."

I planted my lips on the head and gave it a kiss, but that was hardly enough for me. Without waiting for instruction, I opened my mouth wide and took the head of the strapon in. I worked my tongue around it, spreading my spit around.

"That's a good boy. Suck my cock baby. Suck it good."

Now with two hands on the back of my head, Mistress began a fucking motion, pushing more of her cock into my mouth. She never over filled me, but each stroke seemed to push another fraction of an inch into my waiting mouth. I did my best to lube the cock each time it entered my orifice, and as it was lubed further it became easier to take. Before long I had taken 6" of the 8" cock, which seemed to be my limit. Mistress was pushing it no further, but she had adopted a nice fucking rhythm, driving the cock in and out of my mouth at a good pace.

"Does that feel good slut? Do you like sucking my fat cock? Do you like being a little cocksucking whore? You're pretty good at this. A natural cocksucker I guess. You were born to suck dick you little slut."

I was in seventh heaven. Having Mistress talk down to me while fucking my mouth was an erotic experience on a level I hadn't experienced in a long time.

"You've got such a good mouth slut. You're taking most of my fat cock, I'm amazed. You're a skillful cocksucker, we'll see pretty soon just how skillful your asshole is. I can't wait to fuck you slut."

I couldn't wait either. My jaw was getting a bit tired from the pounding it was taking, but Mistress Eden was kept a tight grip on the back of my head, continuing to pound away at my face with her lengthy cock.

"I think I wanna fuck you now slut. Get on the bed, on all fours."

I let the strapon cock slide out of my mouth and I got up, crawled on the bed, and placed myself as Mistress had instructed. I faced the headboard and my ass was pointed towards the footboard awaiting Mistress' invasion. Mistress Eden pulled open her nightstand and produced a bottle of lubricant, essential for any assfucking.

She got on the bed behind me and I felt the cool sting of the lubricant, which she was spreading around my asshole with her fingers. She probed me with two of her fingers, fucking them in and out and getting a liberal amount of lube up inside me. Her fingers alone felt so good that I began pushing back on them, hoping to drive them further into me.

"You like that slut? Do my fingers feel good in your ass?"

"Yes Mistress, please fuck my ass. Your fingers feel so good, I need your cock in me" I begged.

Ask and ye shall receive I suppose. Mistress removed her fingers from my ass and replaced them with her thick cock, putting pressure on my anal ring and begging it to open up with her cock. And open it did, as she pushed half of her 8" into me in one hard thrust. I grunted and took in a sharp breath, the pain was intense. It always is the first time in. Mistress held her cock in place, letting my asshole adjust to the size. She leaned over and placed her mouth at my ear, whispering in a sultry manner.

"Does my cock feel good in your asshole slut? You're tight down there. Such a nice tight pussy. Answer me, does my little slut like getting fucked by a big cock?"

"Yes Mistress, I love getting fucked by a big hard cock, yours in particular. I want you to pound my tight ass, loosen me up."

Mistress Eden was in control here, and she let my asshole know by thrusting the rest of her cock into me, burying all 8" of her hard dick inside my rectum. She held it there briefly before pulling it all the way out, leaving me gasping and my asshole gaping wide open. In mere seconds she thrust it back in, roughly fucking all 8" into me again.

The only sound I could manage was a pained groan. It felt so damn good though to be so thoroughly penetrated and dominated. After repeating the pull out maneuever a few more times Mistress Eden settled into a fast rhythm, pumping her hips rapidly and fucking the full length of her strapon cock into me over and over. She was pummeling my ass with her dick, sawing it in and out of me with abandon.

"You're such a worthless little slut. A real man wouldn't need to be fucked in the ass, only pussies take it in the ass, especially from a woman. You're just a worthless cunt who needs to be fucked like a whore, and that's what I'm doing. Fucking you like the worthless piece of crap that you are. Just a tight hole is all you are, a tight little pussy hole for me to fill with my cock."

"Yes Mistress, I'm just a worthless cunt. Fuck my tight man pussy, please fuck me harder."

Normally I jerk myself off when I fuck my own ass, and I expected to do the same tonight, but I guess you get a little extra when you're paying for the sex. Mistress Eden continued fucking me relentlessly from behind but she added a little wrinkle by grabbing my cock and stroking it. She was masturbating me while fucking me, and I was in erotic heaven. She alternated between stroking my dick and squeezing my balls, which has always been a turn on of mine. I love to have them squeezed, kneaded, and abused in general.

The stimulation was getting to be too much for me, and I was close to cumming.

"I'm going to cum Mistress Eden, I'm going to cum. Ohhh, God, fuck me, fuck me hard! I'm cumming, I'm cumming!"

Cumming I was, all over Mistress Eden's hand and the bedsheets. It was the best orgasm I had ever experienced. I'd blown my load with an asshole full of cock before, but having another person on the other end of that cock added something entirely different to the experience.

"Thank you Mistress Eden, that was amazing."

Now that the sex was over, Eden was back to the kind hostess. She kissed me on the cheek and told me that the bathroom was available for my use to clean up. I took her up on her offer and enjoyed a hot shower, a refreshing experience after the brutal fucking my asshole had just experienced.

I emerged from the shower to find the bedroom empty. I put my clothes back on and walked out to the living room where Eden was enjoying another glass of wine.

"I want to thank you Eden, that was amazing. It was the best sex I've ever had."

"I'm glad to hear it Robert, I hope you'll consider coming back again."

I don't know how I could resist.

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