This Thing Called Life

I was cleaning myself up in the sex store bathroom, happy that I had gotten 'Eager' hooked up with his roommate and was also pleased that Tree would see I could earn my keep at the hotel. My ten inch cock throbbed as I washed it off, still somewhat hard, likely due to the Viagra, even though I had just fucked and then shot my load onto 'Eager's, well, eager face.

Stretch meanwhile was cleaning the stalls, he kept a very clean place despite what goes on back there, he's a good sex store manager, I'd say even the best though truth be told he happens to be the only one I know. He still had the store closed down until I was finished cleaning so I was surprised when I walked out of the restroom and saw Halle Berry there smiling and looking me up and down.

Now don't get at me and say I think certain types of people all look alike because it's furthest from the truth, it's the little details I see in different people that turn me and make me attracted. It's just a point of fact that this woman looks almost exactly like Halle Berry in yoga pants and a pink polo shirt. If she was one of Tree's "girls" she either was unfortunately hung or had it taped down real good. Stretch was still in the back cleaning which was good because if he was mopping out here he might have scooped up my eyes that had just fallen out of my head.

"Sorry Mam we're closed at the moment," I said, hoping all those words came out in the right order.

"Well aren't you the gentleman Jack," she smiled and darned if my heart didn't melt.

"Sorry do I know you?"

"I'm not Halle Berry if that's what you were thinking," she smiled while suddenly circling around me like a hawk.

"I wouldn't say something like that," I replied.

"And I do not have a large piece of meat between my legs, if you must know," she said then leaned into my ear from behind and whispered, "at least not yet."

I knew I liked her. My dick was stirring quickly with her proximity and the Halle berry twin thing she had going on, though I don't think Halle would smell this sweet. I had tossed my underwear when I cleaned up so was going commando and she seemed to take notice.

"So it's true, you do still like women," she said again with the circling.

"I have a fondness for them that extends to desiring a right hard mix of DNA swapping," I offered.

"Oh yes, I can work with this, take your clothes off and have a seat Jack," she said and since there was one nearby I stripped and complied.

My ten inches was sticking right straight up and I wasn't even sure what was happening but though you might question why ____________________, you don't question anything a hot black woman in yoga pants has to say.

"My, oh my Jack, I daresay you're hung like a stallion, I can definitely work with this," she said.

She stripped off her top and those breasts looked amazing and real and her nipples were a very dark black and crinkled out as if it was frigid in the sex shop though clearly the way my cock was bobbing around it was exactly the opposite. She went further and lost the yoga pants and sexy red thong. Her pussy was shaved bare and she took both hands and spread it close to where I was sitting.

"See no cock, and you are still hard, and still interested?" she asked.

I could only nod though I think I did it like I was one of those bobble head toys. She started to dance all around me, getting her body so close I could feel its heat but never quite touching me, she kept stopping to whisper in my ear from time to time, things like did I like her tight black pussy and such. Finally she settled near my front and showed me her wedding ring which in the past has been my kryptonite though I managed to maintain my present cock state.

"He liked it so he put a ring on it, however, my boo allows me a little hall pass for something from time to time, do you know what for?"

"So you can go to the bathroom at will," was the only idea I had.

"No, it's so I can ride some white boy's hard cock," she said.

She reached down and held my cock upright and aimed it at her dripping pussy and inserted just the tip. She held just the tip there for a bit and stirred it around. She was breathing hard as she did so then she pulled it out and rubbed the head of my dick around her clit and moaned even better. I was throbbing and drooling pre-cum, she was so hot but I wasn't touching her none at all I was letting her do whatever she was planning.

Then she put it back in and this time sat all the way.

"Oh my," she said and sat there for a minute, I wasn't complaining none.

"Oh yeah baby, you're white cock feels so good in my tight black pussy!" she yelled and started to ride me hard up and down.

I started to fuck back too but I was gripping the legs of the chair, still not touching her though she now had her hands around my neck and her head pressed to mine as she fucked me so hard and fast.

"Yes Jack, oh fuck me Jack, fuck me with that white dick! Oh yes it's so big!"

I was honored she was calling my name but confused that I still didn't know hers. Her body had started to sweat and her breathing was getting short and raspy. She found a good rhythm and I could tell she was building towards something.

"Oh yes Jack, I'm going to cum soon baby, can you do one thing for me Jack, can you?"

She pressed her forehead to mine and looked me straight in the eyes as she sped up her rhythm. I nodded my head against hers in agreement though I wasn't sure what she wanted.

"I want your cum in my pussy, can you cum with me Jack, can you shoot your hot cum into my wet pussy stud?"

I certainly could I thought to myself and then we were both really going for it, both breathing hard, her eyes still locked on mine in the moments I could keep mine open. This woman had talents, and then...

"Oh shit, yeah, I'm gonna get it, I'm going to come in your black pussy," I yelled.

"Yes baby, give me that cum, give me that white boy cum, oh, I'm feeling it, oh yeah baby, fuck my black pussy, fuck it, fuck, oooooooooooooohhhhhhh!"

"Yes here it comes, I'm going to cum in your pussy, I, aaargggh, yes, oh fuck, yeeeeeaaaaaahhhhh!"

I gripped the chair harder and thrust myself into her as deep as I could to get all my cum out as she continued a slow grind while coming down from her own orgasm. Then she kissed me and collapsed against my body, me still inside but certain I could come no more, it had already been twice. We breathed together, tried to get our pulses down and finally Stretch emerged from the back.

"So I see you've met my wife Sarah," Stretch said.

I was ready to bolt and was mumbling some sort of apology but Sarah grabbed my shoulders firmly and told me not to move so I just sat there starting to soften in her pussy as some cum dripped out of her and onto the floor. Stretch also gave me an "it's okay" nod so I settled down.

"Might I say how lucky a man you are Stretch," I offered.

Stretch just nodded and took his seat; he never was the talking sort.

"So now that you know my name is Sarah, I've got to tell you I am going to be your best friend," she said.

"Uh-oh, when a woman says that it generally means no sex" I countered.

She stood and lifted herself of my clock which dropped heavy against the seat, now soft but still thick and full with its recent exercise. Some more cum poured out of her and onto the floor.

"Shit Jack, your balls are packing, very nice. Now you are right, we will never have sex again, I'm mostly faithful to Stretch, just the occasional tussle with Tree and the occasional white boy as I mentioned, that being you," she said.

So she was somehow connected with Tree.

"Much obliged to the two of you," I said.

"But even though we're never going to have sex again you are not done here, not by a longshot. Stretch," she said.

Stretch hit a button and a door behind him buzzed open. Sarah took me by the hand and led me into a small room with a bed, several computers and television sets and lots of sex toys out and about. A chair bolted to the floor centered the room and that's where Sarah sat me down and quite quickly fastened my hands to the chair legs with foot long Velcro bindings and then the same to my legs. I couldn't move an inch and my mind flashed back to the room with my Mistress, except here I was even more immobile.

"Now Jack, the reason I have you here is because I need all your cum," she said.

"No offense but all I had left in the tank is inside you right now, I already done cum twice and I know I can't get anymore going," I said confident.

"No Jack, we're going to get all of your cum, all of it," she said and turned away.

"When she turned back she had a strange looking device that looked all the world like a cow milking machine. She settled the transparent tube over my dick and nestled it all the way until the end touched my belly. I was soft though so she had to hold it in place.

"There's a machine called the Sybian for women Jack, an amazing toy that I cannot get enough of, it will make any woman cum many times. This here is the male version," she said.

"It's different for women, men can't just keep going, I'm soft you can see even though you are so hot and still nude, I need more time," I said, slightly nervous now.

"Jack, it's a machine, machines just keep doing what machines do," she said.

Then she kept her hand on the tube but with her other she hit a button attached to a cable connected to the device. Suddenly a suction sound and my cock was gripped super tight right at its base. It ached slightly as I was still sensitive from my second cum. She let go of the tube and I was surprised it was not letting go of my cock even though I was soft.

She hit the controls and then suddenly a mechanical up and down sound started and suddenly it was stroking up and down the length of my cock, just like a milking machine. I yelped in discomfort.

"Sarah, please, this doesn't feel good, I can't cum again," I begged.

"The machine will prove you wrong," she said.

And I was worried she might be right, my cock was starting to stir even though it felt uncomfortable, deep inside but pleasurable somewhat what the machine was doing. I'd had no end of new experiences since meeting Tree. Sarah starting circling the chair, touching my body here and there and stopping to whisper parts of a monologue she was just starting. Her touched were making matters worse for me down below.

"So here's the thing Jack, I'm your coach. I will be your personal trainer to get you into the right female body type of shape and I will be your stylist who will help decide your look," she whispered.

That was it; I was getting hard and very excited at her words. I decided not to talk back because I loved everything I was hearing.

"You've got a lot to work with Jack, more than most of the other TGirls, and that doesn't stand for what you think it does, it stands for Tree's Girls, and you are going to be one of the hottest TGirls in his stable when I'm done with you," she said.

I was getting very hot and excited and the constant rhythm of the machine had me stiff but I was able to last because of how much I had come. She rubbed both hands through my hair, looked me in the eyes.

"I think we could grow this out long and we have a fabulous stylist but no, I think we should shave you bald and go with wigs. We have the highest quality. You see Jack, for many men or women who change it's about sexual identity but for Tree's Girls it is about nothing but the sex, the constant desire, the constant need,,,"

Did I mention there was a milking machine attached to my cock?

"So there will be therapy, you will live as a woman for some time before we switch but I don't think any of that will be needed, I think you are a deep down slut. So this what we're doing today is a test that will tell me all I need to know about whether you are ready to get some tits. And not just any tits, with your package we need to go big, imagine all the boys seeing such huge tits and a huge hard cock?"

"Oh fuuuuucccckkk, oh shit, I'm cuuuuuummmminnnnngggg, aaaaaarrrrrggghhhhh!" I screamed.

Her talking had pushed me over the edge. Despite the discomfort it felt amazing having what little cum I had left jerked out of me without anyone even touching my cock. But almost as quickly I softened again and suddenly really felt discomfort.

"Oh Sarah, please, I surrender," I begged but then I noticed she wasn't there.

Suddenly I felt a slick coolness reaching under my ass on the seat. And then something hard cold and metallic began entering my ass. I tried to pull away but couldn't go anywhere but suddenly I felt the object was curved and the bulbous end of it stopped right at my prostate. I groaned in pleasure even though I was in some major discomfort elsewhere on my body.

I ground my body so that it settled and held in place right on my prostate. What felt good to begin with suddenly felt incredible as the metal rod began to vibrate. I moaned despite myself and then Sarah was in my ear again.

"You like that you little slut," she whispered.

"I do but I just can't cum anymore, I can't," I said and believed it.

"Well Jack that's a prostate vibrator in your ass but the other machine? That's been on the slowest setting, so let's see what ten can do," she said.

She hit the switch and suddenly the machine started pumping like crazy on my cock. Any other time it would have felt amazing but right now it was uniquely painful. She started her walk again and I wondered if she was picturing every little thing she was going to do to feminize me.

"This test I'm giving you today is to take your cock out of the equation. You see when you are on hormones for a bit you may lose some of your cock function, so I want to test your desires without a cock in the equation, without a need to come," she said.

I was going to tell her I was already at that point but every time I opened my mouth to speak it shifted my body ever so slightly so that I could only moan at the sensations coming from my prostate. I knew I must be dry because normally I would be leaking some heavy precum if my prostate was getting this kind of workout but I felt nothing leaking down there.

When Sarah floated back around she was in a sexy bra and panties which was somehow sexier than when she was naked. The crotch of her panties was soaking wet, apparently she was enjoying our time together. She held up and IPad in front of me showing an account with a very large sum of money. I managed to ask what that was through my groaning in pain and pleasure.

"It's your account silly. For the jobs you have done and your clothing allowance as you will need all new clothes and Tree wants his girls only wearing the best. I'll also be your personal shopper, I'll help you learn to walk in heels, we start you on a tread mill, it makes your as perk right up and out to show off for all the boy, you like that Jack," she asked.

I groaned and moaned as the vibrator did its work but also because the amount of money in 'my' account was three times what I used to make in a year. If that's how tree treated his ladies I certainly wanted to be one and it was the thought of Tree and the most amazing biggest cock I had ever seen entered my thoughts and brought me hard again in the machine. I grunted through it as it wasn't pleasurable but I was shocked and a little proud I could get hard again.

Then Sarah rolled a flat screen on a cart and positioned it in front of me. She then approached me with a pair of wireless headphones.

"Men do all kinds of things when they are horny Jack, often things they regret right after they come so getting all this come out of you isn't your test, your test will happen soon. These videos will get you ready, get used to watching them, we use them often," she said and placed the headphones on my head. She then hit play and suddenly images of women enjoying men and getting fucked filled the screen.

The images were incredible and there were screen caps and voices urging me to be a little sissy boy. Soon the women were taking facials of cum and soon there were lots of women with large cocks and it began to get difficult to tell which women were which but the common theme was cock were to be worshipped and cum was better than caviar. The videos combined with the machines was doing its job, I felt it building but couldn't believe it.

Then a scene where a woman with a real pussy was getting a facial from three guys appeared and as the last one unloaded she convulsed in orgasm to the disbelief of the trio squirting on her. I saw in her how I was with tree and Mistress, just fucked into oblivion to levels I never knew were possible, to the levels that I was soon to proudly become a TGirl and then it came.

"AAAAAArrrggghhhhhh! Oh I can't, oh, fuuuuuuuuuucccckkkk, ahhhhhhh!"

I focused on the pleasure in my ass but my dick was squirting dry I was pretty sure but in fact I had come a fourth time. Sarah yanked the milking machine off and I thanked her louder than I planned for stopping it. She stroked my cock hard and I begged her to stop and it started to wilt. She reached around and turned off then removed the vibrator.

She undid the straps and I attempted to stand and fell right back on my ass.

"Don't try to stand yet Jack, let the blood get back into your legs. So I take it you don't want to fuck anymore right now right? You don't want to cum anymore today?"

Today, how about never I thought to myself but just shook my head no. Then Sarah stood in front of me and moved her panties to the side and exposed her inner pinkness, it was lovely.

"So would you like to do anything with this Jack?"

"I would absolutely love to go down on you right now and lick you until you scream but no offense I can't do anything with my dick right now," I said.

"After all that you still want my pussy?"

I nodded and she smiled.

"That's what makes you special Jack. You truly do go both ways and we have clients on both sides who will enjoy that. And you are still ready to go when your cock is not an option.

"Passing up opportunities is not in my nature," I said and finally found my feet. I walked towards her, ready to go down.

"Remember Jack, we'll be naked women together many times but we will never have sex again, I get too attached and I love my husband even though he partakes often of Tree's girls. I'm not the test Jack," she said.

She moved to the door and yelled for "the boys" to enter and four black men in their twenties entered, one of whom was wearing sweatpants commando and was hanging halfway to his knee. Another had an enormous bulge but was compact, huge, must be large balls. They weren't particularly clean I could smell them from where I stood.

"This is the test Jack. This isn't a paid job, you have no obligation and we know you have no desire to cum so you can walk out right now or you can stay and show these friends of my husband a good time. That's the test. What are you going to do Jack?"

In my mind there was only one choice.