Giving My Ass to a Wealthy Stranger

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Straight young man dolls himself up and services cock.
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shyscholar
shyscholar
198 Followers

And just like that, there I was standing in a stranger's kitchen wearing women's clothing waiting nervously to be fucked by a real cock for the very first time. This is crazy, I thought, I can still get out of here. I'd hardly ever even seen another man's cock and certainly never touched one. But I'm about to let a complete stranger bend me over, put his fully erect dick all the way inside me and ravage me with it until he was satisfied? This is completely fucking insane.

My heart was pounding. I could feel it in my chest, down into my belly, and deep in my balls. "Don't orgasm from now until you meet Mr. Hammond," Kaitlin had told me one long week ago when we met to sign my contract. "He likes it when his girls make a mess. A big mess. If you cum all over yourself, he'll leave you a fabulous tip. That's what the other girls say," she told me with a mischievous wink.

I pulled out my phone and looked at my bank account. The fresh deposit of $1550 from the so-called "Forbidden Springs Publishers" was still there, clear as day. It was all there: $750 for my escort commission, $200 as a first-time bonus, $400 for letting Mr. Jake Hammond set up cameras in the bedroom and $200 to allow him to finish "wherever he so chooses" as Kaitlin had told me, "and however many times he finishes," again with the mischievous look.

I hiked up the bottom of my dress and ran my fingers slowly up my leg. The smoothness was still very surprising but pleasing. Without hair, the flesh on my leg was particularly sensitive. When my hand reached the panties I was wearing, I cupped my packaged and immediately felt my own warmth through the thin silk. I am so fucking horny, I thought and could feel myself getting hard from the stimulation. I slipped my hand into the panties—my panties—and pushed my fingers back toward my butt cheek. I dragged my pointer finger across my little pucker and couldn't help but gasp out loud.

I leaned on the kitchen counter with my other arm, put my head onto the counter and moved my finger back and forth across my pucker. It was incredible, that sensation throbbing in my anus, launching sparks of pleasure to the surface of my skin in every inch of my body. It had all happened so fast...

About two months ago, I was sitting in a café in the Financial District applying to a few jobs when a cute girl came up to me. Blonde, with red lipstick and an adorable button nose. She introduced herself as Kaitlin. She was disarming, flirty even— but elusive. I would soon find out why she was there—not because she was attracted to me but because of a certain Mr. Hammond, one of her clients. We got to talking and Kaitlin was excited to find out that I was looking for work or some quick cash. She asked me a few things, including if I were "open-minded" and "adventurous, even physically". She said that she did targeted recruitment for well-to-do clients.

"What kind of work is it?" I had asked unsuspectingly, "What kind of skills are you looking for?" Kaitlin responded by saying that her client had assured her that I had exactly the qualifications he was looking for, and that if I wanted, I could make up to $2500 in just a few hours, without committing to anything long-term.

Of course it sounded too good to be true. She gave me a card to Forbidden Springs Publishers, told me to click on the About page, scroll down to the bottom and type in a password, which she wrote on the back of the card. "Do that when you're at home though, not here." She said if I were interested in earning some money, to call the number—she would answer "even months from now, but the sooner the better." And then she was gone.

My curiosity had been piqued. I immediately went to the website to the About page and typed in the password. Soon, a video started playing. It was the testimonial from a slight young man with blond hair and green eyes sitting on a couch. It had all the markings of a tacky sales video "When I first heard of Forbidden Springs, I was skeptical," he said. But then it cut to a shot of him at a spa, a shot of someone waxing his legs for him, then his chest. Then a shot of him in a platinum blonde wig having makeup applied to his face. Suddenly he was in lingerie and heels and he was walking sensually, his head turned coquettishly to the side. He hooked his fingers onto the corner of his panties, ready to move them aside— I closed out of the tab as fast as I could. I nervously checked around me to see if anyone had noticed. No one had seemed to realize.

What the fuck?!? I thought. What was this? A crossdressing thing? Where was this going? What did Kaitlin want with me? I had wanted look for more jobs but just couldn't concentrate after that. The fabric between my legs seemed particularly noticeable and I had been feeling aroused. I rushed back to my apartment, locked my door, went back to the site and started the video again. There he was, that same young man walking around in lingerie and heels. I was completetly mesmerized. He actually looked sort of—I was ashamed to say it—hot. Dressed as a woman, his ass looked appealing and I found myself aroused by his slender body. His skin was smooth, his body tight. His face looked pretty like that... like a woman. I could see his package bulging beneath his polka-spotted panties. Then, then was a clean-shaven black man standing behind him embracing him. No, embracing her. Kissing her. Getting serviced by her—by her mouth. I couldn't stop watching. It was turning me on. I was watching that young man suck a long black cock and enjoy it. He— she was on her knees, messily slurping on those big balls, swallowing the length of that dark shaft and gagging as the man rammed his shaft into her throat.

Then she was getting fucked. Brutally. From behind, on all fours, hips bucking like an animal in heat. She was moaning like a young slut and when her eyes moved up toward the camera there was a distant look in them. Behind her messy mascara and smeared lipstick was a look of agonizing pleasure. As I frantically unzipped my pants, grasped at myself and started stroking my cock she began to beg. Her little cock was flopping around uselessly as she wailed, "Yes, Daddy. Fuck me Daddy. Please Daddy, pleaaaaase!"

Between grunts, the black man in the video demanded, "Please what, you fucking slut? What do you want?" I was transfixed. Tell him, I was thinking, tell him what you want, you filthy whore!

"Cum, Daddy, please. Cum inside me. I want your cummmmm! Please, please Daddy, I need it!" She bucked her hips even harder and let out a guttural animal moan. I couldn't hold back, I started spurting just as the man in the video did—all over myself, onto my shirt and all over my hand. I came so hard, some of it even shot out so far it hit me on the side of the neck and chin.

After eight long, anxious weeks without any prospects of a job I finally worked up the nerve. I picked up the phone and called Kaitlin. I'd barely been able to pay rent and had kept glancing at her business card almost every day, I'd also watched all the other videos on the secret part of their site. There were only six videos they had posted. Six "girls", each thoroughly servicing a different decently good-looking man. I had blown my load to each one of them multiple times and always felt a little embarrassed but intensely aroused, even after cumming.

When I called Katilin last week, it wasn't just that I really needed the money. That was there, of course, but the prospect of becoming one of those slut "girls" thrilled me and made me cum harder than I ever would to any other porn. I wanted to be taken and dominated like that by a powerful, rich man. I wanted to please a big hard cock as thoroughly as they did. I needed it.

It was just over a week ago when I called the number. Kaitlin arranged to meet me the following day, last Friday, at the same café. She said we had to make all the arrangements in person and reiterated that I could make up to $2500. "Also, I should mention that the client who requested you isn't in any of the videos you may have seen on the site. I can show you him to you but only after we sign your contract and confidentiality agreement. Does that sound like something you'd be interested in?" I agreed, not sure if I had made the right choice.

When we met last Friday, Kaitlin was in business attire just as when I first met her. She was very professional and swiftly got me to sign consent forms and confidentiality statements. She showed me Mr. Hammond's most recent STD test and I gave her a copy of mine.

It was surreal: in the casual bustle of the café, she had asked me to review a form detailing what services I would consent to. It seemed crazy that people were taking coffee breaks and typing up emails right next to us as I was checking off that I would suck a stranger's cock, allow myself to be penetrated anally without a condom, swallow cum, take a creampie it in my ass and allow clients to put up to 4 fingers inside me, plus anything else I verbally consented to in person. I could have earned an additional $500 if I allowed the video to be published on their website and an additional $450 if I would consent to being double-teamed. But I just was not ready either of those things.

Kaitlin then explained how I were to arrive at the Forbidden Springs spa the morning of my "date" to be pampered and prepared—waxing, nails, lashes, enema, the works. "You will need to be clean and pretty for our client," she explained, "inside and out. You'll just love how we take care of you." She handed me a folder with photos of Mr. Hammond. I was pleasantly surprised. Though I'm not attracted to men, I could see that he would've had no problem with the ladies. Well-built, short-cropped black hair, square chin and his blue eyes had an intelligent twinkle in them. It looked like he was mixed race of perhaps Mediterranean. "You can hold on to those," she said, "Just make sure you remember: this must all be kept confidential." I nodded silently and stared as his picture, feeling nervous. Or excited. Or both.

"One last thing," she said as we were parting ways, "I almost forgot. Mr. Hammond would like to know your name." I knew what she was asking. I had thought about it a lot already. "My name," I told her feeling slightly giddy, "is Claire." Kaitlin smiled. "That's a very pretty name. He'll be very pleased to meet you, Claire."

And there I was as Claire, just one week later, in Mr. Hammond's apartment for the very first time. I breathed heavily with my head still down, my finger still dancing on my little virgin pucker. I closed my eyes and imagined what was going to happen to me in about an hour. It would not be a gentle finger but a much, much thicker cock. As I begged, it would be brutalizing me like those other "girls"—

I sprung up straight, my heart in a knot. I can't seriously be doing this, I thought. I worked my way to the bathroom so that I could wash my face. Shit! I have makeup on I realized once I got there. But then my eyes lingered on my own image in the mirror. I was engrossed looking at myself like this. They had done a terrific job at the Forbidden Springs spa.


They had given me a shave, plucked my eyebrows treated me to a long, relaxing massage and a herbal facial. With makeup on, my eyes popped attractively, my lips plump and feminine and my brown skin looked soft, flawless and delicate. I never had a powerful jaw like so many of the bigger, stronger men I admired. Women always said I was "cute" more than anything and thought that had disappointed me before but now it paid off. I was happy to look petite, girlish and downright pretty with my soft features. At the spa they had also attached a luscious black wavy wig. I was almost unrecognizable. If I didn't know it was me that I was looking at, I may have thought I was just an attractive young lady. I smiled a coy smile and timidly uttered the words, "Hi, Mr. Hammond." Pouting my lips in a way I found sensual, I whispered, "Do you want to fuck my pussy?" The word pussy set my insides ablaze with an animal heat. I need to play with myself, I realized, right now.

I hurried into the bedroom. When Kaitlin showed me around the apartment just minutes ago, she pointed out the cameras in the room—one on the bookcase to the side of the bed. On the other side were three large mirrors, the sliding doors of Mr. Hammond's closet. Not only would I be able to turn my head to see myself getting railed in an hour or so, but the camera would record it too, from both sides. The second camera was in front of the bed on the desk, set up on small tripod. This way, he would be able to see my face as I got fucked, or my ass, depending on what he wanted me to do.

I just couldn't take it anymore. Even before Kaitlin ordered me not to cum for a week, I hadn't masturbated for a few days. I felt like my groin and insides were on fire with anticipation. My cock, though only semi-erect, was pulsing. 6:37PM said the clock on his wall. He'd be there at 7PM, so I had a little time. I turned the cameras on and scooted up into a sitting position in the middle of the bed to record a little pregame show. I dug into the purse filled with goodies that Kaitlin had given me last week. She had told me that if I were to stay on with the company I could keep them. She had said, "Practice a little each day if you can. Train yourself with these toys if you're not used to this kind of thing. We truly want you to enjoy your date with Mr. Hammond but that can only happen if you're ready to accept what he has to offer, you know what I mean?"

I had nodded earnestly when she asked me that last week. Kaitlin had leaned in and lowered her voice so the couple at the neighboring table wouldn't hear her, "He's 7 inches, but thick. Make sure you can take the bigger plug. Get comfortable with moving it in and out." I had felt my face flush at the prospect of it.

But I had taken it— the fat pink plug—if only in the last two days. I'd sat all the way down on it, making a lube-filled mess in the shower after working myself up through the other toys, increasing thickness or depth a little each day.

One of the smaller plugs had soft ribs on it and felt utterly incredible, like nothing I'd ever experienced before. It was my favorite! It had dark blue stripes on light blue and I was endlessly fascinated by how erotic it looked moving into me, with my dark brown flesh while my pink pucker expanded grotesquely to take it. When I had squatted down onto it, even the with the shower water running it kept causing my ass to make loud squelching noises. I was afraid my roommates would hear, but it was not enough to stop me from impaling myself on it over and over and moaning quietly like a wanton whore. My cock had poured out precum almost nonstop and I was dying to orgasm but somehow managed to discipline myself not to. I have to save myself for Mr. Hammond! I kept thinking every time I felt the urge to cum welling up from deep within me I'm only allowed to cum when he's inside me. The fat pink plug, however, had been very difficult to take and not particularly pleasant. I'd had to move down on it very slowly and adjust to the feeling of so much girth.

But now, in this Mr. Hammond's room, I pulled out the long black dildo with the suction cup at its base. I spread my legs and pulled the dress up so the camera on the desk had a good view of me. I rubbed its firmness against my thigh. It was slightly less thick than the pink plug but convincingly shaped like a cock, and its texture and hardness actually felt like my own cock. A few days ago I had used the suction cup to stick it onto my shower so I could slide back into while standing up. It was pleasingly heavy and now in Mr. Hammond's quiet room I started rubbing it against my cock. I glanced nervously at the camera, then slid my panties down. My dick looked small compared to the black shaft I grasped in my hand. I touched its rubbery cock head to my fleshy one, rubbed the length of it down mine.

I wanted to practice putting it in my mouth, too. I'd never given a blowjob before and Mr. Hammond would be expecting an enthusiastic servicing from my mouth soon so I knew I should warm up. After lubing up the length of the dildo with my saliva, I started moving it into my mouth, slowly in and out. For some reason, I'd never realized how difficult it is to put a cock in your mouth! All the women I'd been with made it seem relatively easy. It was so long! The width wasn't all that easy either, not for my smallish mouth. I crammed the shaft further down into my throat and felt a tingling gagging sensation.

But I was enjoying myself. I'd moved my panties down to my knees, was fondling my cock, balls, perineum, and anus, shoving the rubber cock down my throat. I worked some saliva between my thumb, forefinger and pointer. I pushed the fingers into my little hole. Oooh, still very tight! It was exhilarating to know that they had cleaned out my ass completely and sanitized it. If Mr. Hammond wanted to ream me in my in the ass and then have me suck him off, Kaitlin told me I was to comply without hesitation. Would I be ready for that? I pushed two fingers into myself. Fuck, that feels nice. Some milky precum had pooled in my foreskin at the top of my cock and was dripping down the side. I dipped the dildo's cockhead into it, then stuck it back in my mouth. It was salty, tangy, and delightful.

Suddenly I heard the latch begin to turn. Mr. Hammond! I sprung up, dashed the dildo into the bag, yanked up my panties, dried off my finger on my thighs and bounded out the bedroom.

There he was, Mr. Hammond, right in the doorway. He had loosened his tie and in his hand was a bottle of wine in his hand.

"You must be Claire," he said staring at my with his intensely blue eyes and added with an amused grin, "Looks like someone couldn't wait to get started." I followed his line of sight down to my groin. My erection couldn't have been more obvious, protruding obscenely underneath my dress.

"Mr. Hammond! I... I'm. I'm sorry.." I tried pushing it down clumsily, unable to believe I'd already ruined it!

He laughed heartily. "Please, call me Jake. I appreciate that you couldn't wait. It's... enticing. Here, Claire. Open this up in the kitchen for us." He extended the wine bottle to me. I took it sheepishly and walked into the kitchen. I noticed he stayed a few paces behind, checking me out.

But in the kitchen, he was all over me after handing me the wine key. He pulled me close, standing behind me with his hands on my hips. I was already worked up and could hardly focus on the wine. I could smell his sensual musk, could feel his power and warmth behind me. Is that something against my butt? I couldn't be sure. I was trembling.

"So, Claire, how do you like your new clothes? I picked them out myself. I think you look absolutely stunning. But what do you think, Claire?" I could feel his warm sensual breath on my neck. He started kissing me there.

"Thank you! They're beautiful. And Comfortable. Liberating!" I started giggling nervously and was still fumbling with the bottle. I knew he was had power over me—he basically owned me completely. Mr. Hammond—Jake stepped away, came back with some glasses, relieved me of the bottle and poured us two heavy glasses pinot noir.

He spun me around by the shoulder, handed me a glass and offered a toast. "To my new gorgeous friend, Claire! May she always be sweet, receptive and willing." He gave me a knowing smile and moved his eyes slowly down the length of my body.

I can't believe how fast this was happening, I thought and took a huge sip from my glass. But he is likeable and good-looking.

shyscholar
shyscholar
198 Followers
12