The Hookup: Beginnings

"Smile baby, that's so sexy to watch you diddle your hole." I looked up and he was shooting pictures.

He tossed the towel on the bed and knelt up behind. A pillow propped up the opening even more and I felt him direct the tip to my indented pucker. "Horny little bitch. Showing a man your cunt like that. This is what you want."

He had me around the waist and upper leg and pulled me onto him. The flesh parting flesh in a slurp and without a pause. The hole spread to accommodate as it squeezed the shaft and I now had a cock deeper than had ever been and it made me light headed.

"Uhhhh . . . Take it, take it. Oh god you have a sweet pussy for fucking." He pulled me in tight and the scratchy pubes rubbed against the sensitive flesh surrounding my hole. There was a slight pull out and then he rammed home again. "Ahh . . yeah. So sweet. Rub one out baby while you get fucked."

They were long strokes that sometimes came out and sent a shockwave of sensation through my nethers. I reached down and grasped myself as the rhythmic slapping of flesh and squelching filled up the room with our panting.

He gave it to me hard and constantly before pulling out and rolling me on my back. My legs were pushed back still kept together by the lace constraining my thighs and the pillow shoved under my hips. It was a brief respite and then he was in me again hard.

My hamstrings complained but the shaft rubbed deliciously on my gland for a new version of pleasure pain and I tried to relax. We grunted from the coupling. Two men rutting to their release.

And it came for me first and I splashed jism up my stomach and chest as my balls contracted and emptied.

Richard let my legs down and moved up to my face. The wet towel wiped his member down and he presented it to my opening lips.

I sucked the head and stroked his balls which got a grunt. I wasn't particularly experienced and good at giving blowjobs. In fact I had never made a man cum from it before. I wanted to change that. To cause a cock to explode in my mouth, on my face, down my throat.

My hand reached farther, stroking behind his balls and I felt him lurch and he went even harder in my mouth. I reached up and some of the copious spit covered my finger. It returned back behind his balls and I felt the ridge which I slid further back to corrugated skin.

"Ahh, gonna feed you soon if you keep that up." I tapped at the crease and then stroked forward while taking him as deep as possible in my mouth.

The first spurt fired without much warning and hit the roof of my mouth. He pulled out and the next hit my lips, then nose, cheek, and the bridge of my nose. The last two spurts dripped onto my chin and Richard swiped the tip across my tongue.

"That's hot as hell. Don't move." He stood and snapped a few pictures of me laying there pink lace panties pulled down, cum all over my face and chest and flaccid cock lolling against my stomach. Then he moved closer until I knew only my face must be in the picture.

"Pull your knees straight back and show me that love hole."

I obediently complied feeling the air on the matted greasy hair in my crease.

"That pussy looks used and so does your face. Do you like that? Being my slutty girl? How do you like it, sweet and tender or hard and dirty?"

"Dirty. I like it dirty. With your cock up my ass leaving a drip that doesn’t' stop for a day. Like right now where you came down my throat, in my mouth, and on my face. Used and desired as a slut."

"Thought so. But that's your pussy. You call it your pussy and that's how we'll do things then. Every time I send you home will be with my load in you. If I get this commission I'll be up here at least once a month. I want you to be my slut when I'm here."

He moved over me and used his cock to swipe at my cum that decorated my belly and chest. It clung to the skin and left a drying film. Moving forward he presented it to my mouth and stopped to take a picture as I sucked it off. He repeated with his own cum using his fingers to get it all and leave a large dollop at the tip. I dutifully sucked that off as the camera shutter sound repeated.

"You're getting me hard again but let's save it and get some sleep. Go take a shower and put your new clothes back on to sleep."

I showered and cleaned up as best I could. My hole was greasy and wet but it seemed like I got the worst of it. I had no doubt the panties would be soaked when I woke up.

It was that dreamless unconsciousness after sex. Like hours just disappeared rather slept through. It may have been the light or the hard length of cock pressed into my crease and rubbing suggestively as I lay on my side.

Richard's hand came over my hip and pushed the panty front down. His fingers grabbed my warm cock and balls and stroked. "Yeah baby, get hard for me."

He stopped for a moment and his hand left me. The sound of the pump lube bottle was followed by the hand pushing at the fabric covering my ass. Unerringly fingers spread and played at my hole. Rubbing and coating the entrance his lips went to my neck.

All the previous action left my entrance receptive and I felt him slide down. The hot flesh found the pucker and didn't hesitate. I moaned as the tunnel spread and accepted as his hand reached around again.

He pulled me back and seated himself all the way up. His prickly fur pushed flat against my ass. "I love it baby. You spent the night in my bed and now getting fucked the first thing in the morning. Love this pussy. Going to drop the morning buildup in you to feel the rest of the day."

He removed his hand and rolled me to my front still ensconced. The new leverage let him move hard and he pumped at my backside. I reached back and spread my ass and he growled in my ear as the flesh slapped.

There was nothing I could really do except lay there and accept the fucking. His morning stamina kept it going for at least ten minutes and he might even have been harder. I could feel the juices starting to flow as the blood heated and I got hard as well. There was a wetness between my belly and the bed as I leaked too.

The speed intensified and then he was deep, groaning and twitching as I felt him unload in big spurts. There was a pause and then he rolled back to spooning. His hand jerked me off then in short order still embedded. The wet hand came up covered in my spend and fed it to me before we just laid in the afterglow.

Finally he fell out of me along with a trickle of juice. "What are you doing the rest of the day? I have to prepare for tomorrow in the afternoon but I'd like one more time before then."

"I need to go home and take care of the dog again."

"Why don't you do that, download that camera and bring me back a flash drive I'll give you with prints of your favorite three pictures. We'll go to lunch and then come back here." He pulled the back of the panties up and slapped me on the ass.

We showered and got ready and soon I was back home staring at the screen at the debauchery. My rosy ass being spread and split. That veiny pillar of meat opening my backside. Causing the flesh to be pushed in and pulled out as it clung to flesh. The open, greasy hole that had his ejaculate dripping out above lace panties. The glazed face, my pointed tongue covered, and the thick meat having recently spent on my face

It was hard to choose what to print and I agonized over it a while before pressing print.

I went back to the hotel several hours later and Richard kissed me at the door. "Before we go I picked up some things. Go into the bedroom and get undressed."

I started pulling off my clothes and soon stood there naked. "Do you have the flash drive and your favorites?" I nodded for some reason feeling slightly embarrassed.

He lay each of the three out. My tongue touched the tip of his cock which had cum it against the backdrop of my cum spattered face. His half engulfed wet cock tugged the lips of my ass on the outstroke. The greasy ravaged hole between my cheeks was partially open and leaking from the cock in the foreground that had just been up it.

"You're a dirty one aren't you? Like playing the slut for me and being my girl. Admit it."

I did. It was a curious sort of freedom. "I do."

"Then tell me you're my slutty girl."

"I'm your slutty girl."

"I thought so and I got some things for you so you'll remember "

He grabbed a bag from the dresser and pulled out packages of black lace. Tugging them open he laid them on the bed. While I had seen pictures of them before I had never seen them in person. Black hose, a corset and a garter belt along with black lace panties.

"Bend over, I have a surprise before we get you dressed and we go out." I couldn't tell him no so I did it. I felt a cheek tugged aside and then the soft yet rigid toy found my opening. It was lubed and I took it easily. Two days of buggery will do that for you. It had an extension that pressed against my perineum and I realized it was a prostate massager. I had one at home so I knew what to expect.

Richard held out a remote and pressed a button that radiated vibrations out that admittedly felt good. "You're going to wear that when we go out and I can use it anytime it's needed."

Besides the vibrations I felt it swell. " And so it doesn't come out it also expands. Got to keep that pussy ready."

I had never been interested in women's clothing before and honestly still wasn't but it was obviously something he enjoyed. Having me pull on the hose and adjusting the seams. Cinching the corset tight so it compressed my waist and created the appearance of cleavage.

I had no clue about how garters were worn but Robert had them on and hooked to the stockings. Apparently panties were put on last so they could be removed without disturbing the garters.

I was embarrassed but turned on by the fact Robert found it so desirable. He had me turn and took pictures from every angle. Leaning over, ass sticking out, the panties exposed the bottom of my cheeks and then not even that when he had me pull them down.

"I love the way the garters frame your ass baby and I can see your toy peeking out. Show it to me sexy."

I reached back and pulled at the cheek nearest him and I heard an intake of breath.

"Oh yeah, keeping that pussy warmed up for me. Pull up your panties and put on your clothes. I can't wait to get you back here."

With jeans and my other clothes on the only thing that might give me away was the hose and they weren't that obvious. I was more than conscious of what I was wearing though. As I finished the massager began to vibrate and swell.

It felt like it was not going to stop and I grunted as my rectum expanded. I jerked as it forced the vibrations against my gland.

It stopped expanding and I lost my focus on anything except that vibrating sensation deep in my backside. It then stopped. "Let's go. We're going to get you so hot to go that you'll be begging for it. You're not going to cum though. Not until you feel me up that pussy."

Lunch wasn't my focus. I ate and drank my beer. I can't tell you what I had. Just when I could regain my wits that vibration echoed up from my groin and I'd stop whatever I was doing or saying.

Robert would get a knowing grin and my cock was hard against the lace leaking. Just when I thought I'd burst the vibration would stop.

Finally the check came as we went back to the room. "Strip and purse your lips" came the direction and I stood there in black lace with the dampness in the front as he applied red lipstick.

"Get down on your knees" and I knew what that meant. That thick cylinder of flesh throbbed just a few inches from my face. My nose twitched at the man musk and the precum started to coat the head.

"Look up at me and put those lips on me. Such a pretty little cocksucker."

I looked up as I grabbed the shaft and saw him looking down smartphone in hand. The tiny lens aimed straight at me as my lips went around the tip.

"That's right. I want video of my cocksucker doing her job. Her pussy getting wet while I fuck her mouth."

I felt the buzz of the massager deep inside and shuddered at the feeling. Richards free hand went to the top of my head and grasped my hair. I pulled my face forward so his cock filled my mouth and I panicked slightly until he rocked back.

"Wish I had time to train you. Give my leg a tap if you think you're going to cum. Squeeze your hand into a fist. It helps with the gag reflex."

I didn't panic this time when it filled my mouth but began to cough as I squeezed my hand tightly. It did help but I was hugely relieved when he pulled back.

That feeling was brief because he then used his hand to start using my mouth as his pussy. The gag reflex would start then subside as the saliva flowed in response.

"Another week and we'd have your nose in my pubes but maybe later." He pulled my head back and his cock left my mouth and bounced lightly on my chin.

"Go lay at the edge of the bed on your back." The buzzing ceases in my backside and I could feel the deflation. I knew it would be replaced with flesh and blood soon.

Laying back in the classic receptive pose Robert took more pictures. He moved forward and had me lift my hips to tug down the sodden panties.

"Pull your legs back so we can get that pussy ready." He grabbed the base and I felt the tug and slither as it was removed to leave my hole slightly gapped and receptive.

He slathered lube on himself and stood between my legs as he hoisted my hips. The hardness poked unerringly at the indent. "Wrap your legs around me and pull me in. I want to feel those stockings as I fuck this pussy and breed you."

I did as he said and pulled him in slowly. It might as well have been a plunger that ejected my cum up my chest in long spurts as I squirmed on his cock. He swiped at the liquid and stuck the gummy fingers in my mouth and I sucked on them. The rest collected on my lips and chin as first pullout and thrust rocked me back.

"Oh you're a hot little slut. Next time we get you all dolled up I'll spatter that face with my baby makers." The thrusts were coming hard for several minutes before he withdrew and rolled me over.

He positioned me over two pillows covered by a blanket, my ass poised suggestively in the air. I looked back and he had the phone out again.

I was surprised when he handed it to me. The front-facing camera was active. "I want to watch your face as I breed you. Press the red button to record and watch yourself."

I stretched my arms out in front of me. The small screen showed a face with smeared lipstick and globs of cum as I pressed record. I could see and feel Robert kneel behind my upturned ass.

I would have thought my reaction by now would be more subdued but the screen showed opened mouth, expelled breath, and the long sigh as he filled me.

My ass rippled with each impact too as he grabbed my hips and pushed in and out. It was so odd to see myself that way. Reveling at being used and a heavy-lidded torpor as he thrust in and out of my rectum.

I felt myself hardening again at this self-porno and raised my ass to meet him. "What a sweet, hot pussy. I'm going to breed it soon and send you home dripping. Take it my sweet little slut!"

He thrust three more times hard and I could see the strain as he jerked and fired his cum up me. At the end put his hand out and leaned forward, still embedded in me. "Did you come again?" he asked.

I shook my head silently and he reached around to find my cock hard against the pillows. He grasped it and I raised back for clearance as he began sliding his hand up and down the shaft.

I could feel his softening member moving loosely in me. The fore and aft stimulation had me moaning and I could see it. Visual, mental and physical stimulation triggered the spurts which he cupped the tip to contain. The strong sphincter muscles pushed him out too as a flow of juices followed and slid down my ballsack.

The video was still running as he smeared my own cum across my lips and penetrated them with his covered digits.

He took the phone from my grasp and with a hand on my back told me to wait. After half a minute a rubbery tip slid up easily and the rim of the plug contacted my cheeks. "Go home full of me. I want it to soak into your lining so you'll remember this. I need to get to work now and make sure I win this commission. It's more than money now."

With that he leaned down and gave me an open mouthed kiss before disappearing into the bathroom.

I cleaned up silently. Leaving his present in while thoroughly washing everywhere else. At the door he pressed a sack into my hand. "Things for the next time" he said and we kissed one more time and I drove home.

I went through what he had sent me home with. I bent over in front of a mirror and saw the jeweled plug nestled tightly between my cheeks. Pulling it out a trickle of semen appeared and the many days of activity showed.

It wasn't the porn gape but I was partially open, the orifice elongated, puffy and no longer round. Curiosity got the better of me and I probed. Two fingers left room, three were easy and four went in. Staring at the mirror I realized how close it was to fisting. Not something I would at all be interested in but an understanding of what a big cock did to your body. How permanent was it? I'd have to keep checking. If it was would it stop me? That was a question I couldn't answer right now.

I felt some shame and guilt as I pulled the fingers out and the flesh followed. Is that what Robert saw as he fucked me. A hungry ass trying to hold him inside as he sodomized it. Those feeling mixed with some pride over how I accommodated and pleasured his large member and extracted all that cum from him. Cum that now flowed from me and covered the fingers I'd removed.

I had a decision to make as well. Would I do this again? Become another man's willing slut and dress to attract and satisfy his urges. If not Robert, somebody else? I'd be lying if I didn't say I'd enjoyed it when it happened. This was the post-coital recriminations. If he said next week that he was coming back for this commission would I be getting bred again wearing women's lingerie for him. Was this really me?

Unlike most things I put this back without touching it. The truth is I wasn't sure but suspected I might repeat this and more if he called. The white and red lingerie he has sent with me implied that feminization was something he wanted. The lipstick and calling my hole his pussy was another.

I was a very masculine guy. How far would I let him take this? I hadn't said no yet and didn't seem capable if I was going to be honest. How far would he take it?

I hid all the evidence and cleaned myself so as to not leave evidence and then went back to living life. The weekend faded into one of those disconnected events along with the soreness. Thankfully my backside seemed to regain some tightness and I decided to not use the plugs anymore.

Five week later I got a text that he had got that commission and would be up here a couple of weeks a month for the next year. Did I want to get together . . .