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  • My Life Pt. 04: My first Client

My Life Pt. 04: My first Client

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Author's note: This is just a vignette from my life. I suppose it could be considered a non-sequential portion of the "My Life" series. Most of my stuff is long, involved and culminates in a sex act as the climax of the story, and yes I meant the double entendre there :) This time I am going for a bit shorter back story and more sex. As always I hope you enjoy and please send me feedback.

*****

I stood in front of the full length mirror that was nailed onto the back of my bathroom door. The pile of unfolded laundry and the cracking walls of my cheap older apartment were at odds with my look and the feeling I was going for so I tried to block it out.

Not that I'm complaining, it felt good to be out on my own and in school. I had a part time job in the computer lab at school, which was super easy. I had a modest college fund from my Mom; she has always been smart with money even though our means are modest. I still hadn't settled on a major yet and I was only an hour away from my Mom and home. Still, I felt grown up. Looking at my reflection in the mirror, I looked grown up.

My long dark hair was done up and pinned with long elegant hair pins, but with two long curling tendrils left loose to frame my face. My makeup was done nicely, but not too extravagant with a dark shade of lipstick. My long neck (one of my best features I think) was encircled by a silver necklace that my Mom brought me back from her trip to India that she took for work. I also had some silver bangles on each wrist. This was framed by the low neckline of my black dress, which showed a nice expanse of skin on my chest.

OK so I didn't have much cleavage being a small breasted girl, but what I had was nicely on display. The dress was tight and hugged my curves. Living alone I had to use a piece of string to zip the back up all the way. This little act made me feel both independent and miss my Mom. Not for the first time I thought I should call her. I didn't though, independence won out.

Under the dress I had on a lacey black demi bra, garters and dark thigh high stockings with a sexy Oriental pattern on them. Over the garters I had on a pair of matching lacey black panties into which I tucked my modestly sized penis. My little girl cock as I call it was behaving itself at the moment because I had satisfied it just before I started getting dressed. This always helps. I topped the outfit off with 6 inch stiletto patent leather heels. My nails were done a dark red to match my lipstick. I felt like a knockout!

I could still feel the lube on my ass from my pampering session. I used a good sized dildo to please myself and get myself ready for what was to come. The truth is I wasn't entirely sure what would happen, but I did want to be prepared. I didn't want to cum too soon or be in pain if he wanted to fuck. After all I was continuing the family business after a fashion.

You see, after my Father left and before my Mom got her degree and a good job, she had done a little bit of sex work. Not a lot, she did some escorting, some "body rubs" and when the car broke down she paid the mechanic on her knees or on her back depending on how bad off the car was. She never had any bad experiences and still saw a couple of her clients, particularly the mechanic, to this day as kind of a thrill from time to time.

My Mom was pretty open with me about sex and even told me about her sex work. She was also super supportive of my transition at a young age and so was largely responsible for the pretty girl (if I do say so myself) I am today. This always intrigued me about her. Add that to the complexity of dating while Trans and I thought it might be something I wanted to try and the money would help for sure. I put out an ad in an online forum and got a ton of responses.

A lot of the responses were creepy, or off or just didn't peak my interest. Then I got this one from a nice looking man who sent his picture, from the look of him he was in his late 50's or early 60's, a bit on the short side with gray hair, male pattern baldness and a well-trimmed gray goatee. He was just my type so I set a date, a date that was about to happen in about an hour. The hotel was only about 15 minutes away down town.

To make a long story short, I checked my handbag for the condoms and little bottle of lube I put in there and headed out the door. I barely registered the ride over and soon my shaking hand was pushing the number 5 on the Sheraton Downton elevator. The butterflies in my stomach were due to more than just the elevator. I was really nervous.

When he opened the door and welcomed me in I buried my nerves and put on the calmest expression I could muster and tried to walk in with elegant poise. He was dressed in a designer shirt and slacks with a really snappy red striped tie. He was definitely a sharp dresser and I was encouraged by the look on his face which was both friendly and clearly attracted.

"Hello, please come in." he said, his eyes following me as I entered.

"Can I get you a drink?" he asked.

"Sure" I replied and he poured me a glass of white wine and took a sip to hide my nervousness.

"You look even lovelier than your picture." he commented.

"Thank you Sir."

"You're also very polite."

"Well, I suppose we should get the formalities out of the way," he said, pointing to a stack of bills on the night stand "this is for you."

"Thank you again" I didn't touch it, I hadn't earned it yet.

He sat down in a big arm chair in the corner of the room. He patted his knee saying "Join me."

I sat on his lap and put my arm around him, his free hand slid easily around my waist and settled on my hip. He was smooth I'll give him that. "You truly are lovely." He said, his hand sliding down and giving my ass a squeeze. It was the first thing he said or did that made me feel like he owned me for the next two hours. It made my stomach do a little flip and I wasn't sure I liked the feeling, but I powered through.

"You're not so bad yourself." I said, wiggling a little in his lap, I could feel his erection start growing against my thigh, which started to turn me on a little.

"I was impressed with your ad, nice legal maneuver there," he said as I sipped my wine, "are you in law school?"

"No, I haven't decided on a major yet, I just thought I should take some precautions, so I read up on the laws and made it up." I told him. I had written my ad as "relationship advice counseling" for $100 an hour.

"Well you'd certainly get off in my court." he said with a wink. I stiffened; I really didn't want to go to jail.

"No worries young lady, I am here to experience pleasure, not judge you." He cut my question off with another squeeze of my ass. "But," he continued, "If you ever do decide to go to law school, you can always clerk for me."

"Thank you Your Honor" I said with a smile.

"Oh yes I like that," he responded excitedly, "keep calling me that."

"Yes Your Honor!" I said with more enthusiasm, giggling. We were coming to the end of our wine glasses and I was feeling pretty warm.

Then he was looking at me intently. "Do you kiss?" he asked.

"Yes" I said with a smile. He moved in and kissed me, our tongues mingling for a while, his facial hair tickled. I could feel him growing harder against my thigh. I reached down and rubbed him through his pants and he groaned into my mouth.

Then I started unbuttoning his shirt. He was wearing a "wife beater" style undershirt, which I love. As I did this I started moving down his body with kisses. He leaned back so he could enjoy me working my way down, his hand groping my left tit, teasing and pinching. When I reached his pants I slid to my knees and kissed his cock through his slacks. He was moaning and enjoying himself as I worked his belt and fly loose.

I felt him lean forward a bit and his hand at my back, he was unzipping my dress. "Stand up" he requested. I did, letting the dress fall in a puddle around my ankles. I stepped out of it.

"Wow" he exclaimed. Then said, "Bra too please." I removed it, the small mounds of my breasts got goose pimples, my nipples hard and pointy in the air conditioned room. "Beautiful" he said in response. I blushed, I felt really exposed just standing there, my little girl cock straining for release.

"I want to see It." he said. I knew what he meant by "It". I reached into my panties and worked my little cock out so he could look. This was tricky emotionally for me because there were lots of things he could say here that would make me feel horrible and send me fleeing naked down the street. He didn't though, he was a perfect gentleman.

He looked at it mesmerized and reached out and tentatively touched it. Then he stroked it a bit, slowly up and down. My little girl cock is about five inches long, fairly thin with a nice slight upward curve to it, which he caressed with his fingers. I closed my eyes and moaned, I felt objectified but not in a bad way.

"I've always been curious." he said, "I'm sorry."

"No need to be sorry Your Honor," I replied breathily, "It's what I am here for."

He let go of me and just looked for another few seconds then shook his head ruefully "I'm not going to last long."

"It's Ok your honor," I replied, "we've got time to get you going again; I'm not in a hurry."

This seemed to really excite him. I walked my most sultry walk across the room and got a throw pillow. I put it on the floor between his feet. He just leaned back watching me in his undershirt and open fly slacks. I knelt down on the pillow and reached for his waist band and worked his pants and boxers down his legs until they pooled around his ankles.

With his cock exposed I got my first real look at it. It wasn't really big, which made me breathe a sigh of relief; it was only about half an inch or so longer than mine but was quite a bit thicker. It was nestled in a nice nest of salt and pepper hair. I took it in my hand as I leaned forward and began gently licking his balls as I worked my hand up and down his cock with a really light grip, barely even touching it.

Then I worked my tongue up his shaft, being sure to keep eye contact the whole time. I just avoided the glistening drop of pre-cum at the tip. I wanted it bad, but I also liked my health. He groaned in pleasure anyway. I could feel him getting really worked up and I was totally enjoying this feminine power I had over him, this powerful man in society.

OK, so who says you can't enjoy some feminist sentiment while on your knees for money?

I sat back on my heels, it was time to get to work for real, and my mouth was watering like crazy. I grabbed my purse and rummaged around for the cherry flavored condom. I ripped it open and maneuvered it to the head of his cock. I put my mouth on it and sucked the head through the ring and then pushed down with my fingers ringing his cock until it unrolled past the head.

Taking him a bit further in I tightened my lips around his cock just behind the roll of the condom. I took him deeper unrolling the condom down his cock with my lips until I took him all in and the condom was on. I could taste the bad cherry flavor with latex undertones all along my tongue. He groaned really loud when I did that. Hehe, my Mom taught me that trick.

Then I was going at it for real. I wanted him to cum. My own cock was begging for some attention, but I ignored it. His cock was perfect in a lot of ways. I could take him all, with the tip just tickling the back of my throat. He felt beautiful in my mouth and I wanted to please him with all my being. My head bobbed up and down as my fingers gently tickled his balls. He was getting close I could feel it throbbing and bucking in my mouth. I heard his moans reach a fever pitch. Damn he was loud.

Then I felt his cock pulsing and the condom got a lot warmer as cum filled it. God how I wanted to feel it flooding down my throat! This is a dangerous game though and a girl has to protect her health, not that I thought he had anything, just you never know. I settled for swirling my tongue around his slowly softening cock, then gripping the condom so nothing spilled out and sliding it off of his cock. I discreetly set it aside.

Not sure where to go from here I just laid my head in his lap and let him caress my hair. Thankfully now that his climax had passed my own little girl cock was less insistent, but I was still supremely horny!

"Mmm," he sighed contentedly, "that was wonderful."

After a few more minutes of just being there together he suggested we go lie on the bed. I took the opportunity to palm the still warm condom and toss it in the nearest waste basket.

I let him lay down first and get comfortable and when he settled I crawled up on the king sized bed next to him. He patted his chest and I put my head there. I draped my thigh over his, letting him feel my stockings on his bare legs.

His right hand traced my areola and teased my nipple. My cock got hard again and pressed against his hip. I rubbed by thigh across his and played with the white hair on his chest. His left hand stroked the back of my hand and soon our hands were exploring each other. This was comfortable, way too comfortable and I was in danger of losing perspective.

I explored the simple gold band wedding ring on his left hand.

"You must think I'm awful." he finally said.

"Mmm," I sighed, "I'm not here to judge."

"My wife and I have been married longer than you've been alive."

I just nuzzled his chest and listened. I let my fingertips wander his chest and belly and stray occasionally down to his slowly awakening cock.

He told me about his life with his wife. How they had it good, they had a grown son and daughter. He confided that his wife was no longer interested in sex and that "these little get-aways" were what kept him in his marriage without being resentful.

They also allowed him to experiment with things he really wanted, which is why he wanted me. It was a little demeaning to be thought of that way, but I didn't get the impression that I was only a fetish object, but a real person in his eyes. Just someone who could provide the experience he wanted to have.

By the time he was done talking his cock had mostly hardened and I was gently stroking it. It felt really good in my hand. He stopped me and got up to go to the bathroom. I took the opportunity to go to my purse and get out the bottle of lube and another condom. I set these on the night stand next to the money he'd laid out. I got comfortable on the bed again by the time he returned.

He stood at the end of the bed looking down at me and stroking his cock to full hardness. I was stroking my cock lightly and playing with my nipple trying to be sexy for him. It seemed to be working. He crawled onto the bed and knelt over me. He reached out and grabbed my cock.

"I want to try this." he said and leaned down tentatively. Then he put the head in his mouth and sucked a little, then a little more. I moaned sexily, but it was a bit of theater. It did feel good, but to be honest he was very hesitant and unsure so it was kind of awkward. Still I wanted him to feel like he was pleasing me. This became much easier to do when he wet a finger in his mouth and started fingering my ass too.

After a few minutes of this he stopped, I guess his curiosity satisfied and sat up. I reached over to the night stand and grabbed the condom and lube. I tore open the package and put it on him. I spread some lube on his now raging cock and then a little more in my ass.

"Turn around." he requested.

I turned over and got on all fours in front of him. I arched my back enticingly. I also happened to catch a reflection in the bathroom mirror of my ass, garter straps and dark stockings contrasting with my milky white thighs. It looked really good, heck I would have fucked me right then!

Then he was behind me, one hand on my hip, the other guiding his cock into me. He pushed himself into me and I moaned as he pushed in slowly until I could feel the roughness of his pubic hair pressed against my ass.

"Oh god," he said urgently, "hold still." His hands had an iron grip on my hips as he struggled to control himself. I moaned, I couldn't help it, the whole damn thing was so sexy.

"Shhh!" he demanded and sounded like he was in pain, "please" he added more gently.

Then he seemed to regain composure and started moving, just little thrusts at first. I bit my lower lip and gripped the sheets trying not to make any sexy noises. God he felt so good inside me. He built up thrusting longer and harder. Before long he was fucking me hard and fast and all thoughts of me being quiet were forgotten, I was openly moaning with each thrust now and he was grunting like an animal, his hands still on my hips controlling the pace.

Then he reached forward and pulled out my hair pins, and my long hair fell across my back and shoulders. He gathered it up in one hand and pulled back, forceful but not painfully hard. His other hand was still on my hip as he fucked me harder. His hips were slamming into my ass making loud slapping noises as he drove his cock into me. My tits, small as they were with bouncing and shivering with the impact of his body into mine, my little cock bouncing up to slap my belly sending shivers of pleasure through my body.

Then he thrust me off of his cock abruptly. I fell forward and looked over my shoulder to see if he was cumming. Instead he was trying hard to control his breathing, I guess he wasn't done with me. Once he got his composure he flipped me over and I was surprised at his strength. Immediately he was up between my legs, pushing his cock inside me again as we embraced face to face. He kissed me deeply.

He maneuvered his under me and gripped my shoulders and used the leverage to thrust deep, never breaking his kiss. Then he was thrusting and building speed faster, his mouth all over me, on my bouncing tits, my neck, biting my shoulders as he fucked me silly. We were building to a fever pitch again and I really wasn't sure how much more I could take. He sat back on his heels, pulling my hips with him, his cock buried in my ass.

"I want to watch you cum." he said breathless.

I nodded between moans and reached down to rub my little girl cock for him. His pace picked back up as he looked down on me and fucked me hard and fast. It didn't take long. My back arched and my whole body shuddered.

"I'm gonna cum!" I cried out, "Fuck! I'm cumming!"

I felt the wet heat of cum splashing across my belly as I nearly screamed under his slamming body. My eyes practically rolled back in my head and I swear I was close to passing out. It was just that intense.

Before I even had a chance to calm down he was pulling out of me and ripping the condom off of his raging and throbbing cock. He moved up my body, pumping it hard and fast in his fist until he was over my chest.

I arched my back and pushed my tits up as much as possible. He was grunting like and animal above me. His hot cum sprayed more than shot out, covering my chest, I tilted my head back just in time for his hot cum to coat my neck as he groaned and pumped his cock.

Finally the last few shots of cum burst from his cock in decreasing volume, he was breathing hard above me. He rubbed the last bit of cum off of his cock on my nipple. I collapsed into the bed spent and covered in hot cum. The smell in the room was an intoxicating mix of sweat and semen. Wow.

Without a word he got up and went to the bathroom. I could hear the water running and he came back with a warm wet towel to wipe me down. "I should be doing this for you.' I said.

"No sweetheart," he replied, "this is my pleasure."

After he was done cleaning me up, he collapsed next to me on the bed. I rolled into him and put my head on his chest again.

"My time is more than up." he said his fingers tickling my naked back.

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