The Hookup: Beginnings

Contented I fell asleep for I don't know how long and woke refreshed. "Don't move just yet. Give me a minute to finish." Looking over Richard sat in his bathrobe sketching in a notebook. Finally he put it down and I sat up to find the deposit he had made wanted to come out now. Hunched over with a hand under my ass I made it to the bathroom and expelled a considerable amount.

"Sorry, I was afraid of leaking everywhere. Haven't ever had to worry about that before."

"Completely understandable. I hadn't had an outlet for a while so I imagine there was a lot. In fact while you were sleeping I went down to the lobby and picked up some pads. You're probably going to leak for a while." He pointed to maxi-pad packages on the table.

"So what are your plans for the rest of the weekend?" he asked.

"Well I don't have many yet. I have to go feed and take care of the dog but nothing else."

"Could I persuade you to spend it with me after you take care of your dog? Dinner, spending the night?"

I hesitated never having done that before. The new intimacy.

"Oh, and I know you're trying to be discreet so we could have dinner served here in the room. Sort of serves another purpose I have anyway." He grinned at the innuendo.

"Sure. It will take me a couple of hours and I need to pack some clothes. Why don't I shower and take care of things and meet you back here at seven."

He smiled big. "That would be great" and gave me an extended kiss before slapping me on the ass as I went to the shower.

When I finished my clothes were laid out and to my relief he had placed one of the pads there too. The narrow strap wouldn't have retained much and despite trying to clean in the shower I could still feel the drip. I only minded the mess but loved what it meant.

While cleaning out it was also opportunity to see what shape my anus was in. I was not surprised it was loose based on what had been up there but I had been expertly dilated. There was no doubt it was used. My two fingers slid up easily but the ring didn't hurt and the idea it would be plundered again soon didn't worry me. In fact it gave me a little chub to think I'd be getting filled again soon.

I did hesitate when pulling the thong back on. The idea of the strap rubbing against me didn't appeal but the maxi pushed under it cushioned things. I slipped on the rest and left the bathroom to find Robert finishing his sketch.

I was sprawled in that dreamless, after sex sleep. Lying on my side with the sheet tangled around my feet. Hair tousled and exposed to the world. My flaccid cock and balls lay against my thigh. The subtle absence of color in a drip on my shaded thigh and another drip peeking from between my slightly open buttocks. "Lover" was written in script below.

It was erotic as hell and left no doubt to the nature of the love. "Are you an artist?" I asked.

"No, an architect but I always liked to draw and you inspired me."

"That's, that's erotic as hell. Part of me wants to get undressed now and have you do it again."

"Save that for tonight. And tomorrow morning, and however many times we get the rest of the weekend. I'm going to love you, and fuck you and then love you again. Are you ready for that?"

"I hope so. I think you may have made me a size queen though." He laughed.

"If it keeps you coming back then good for me."

I left and drove the few minutes to my house. Thinking of what I needed to do and getting a bag ready. I threw all of my special underwear and jocks in as well as the enema supplies and spare clothes. The dog got fed and got a walk before I realized it was 6 pm and I needed to get ready for the date.

I couldn't help but visually inspect my anus and discovered that my previous inspection was still valid. It had tightened up some which was a small relief but visually was fine. The maxi had been half saturated when I took it off and there was still a slow leak. One that continued and I intended to add to over the next couple of days.

Freshly showered I pulled on the black thong and used another maxi before snitching a couple from my daughter. Thankfully she had lots and wouldn't miss a few. Fresh black jeans and an open necked shirt. As I paused before leaving I debated whether to bring the camera. Part of me didn't want the distraction and part of me wanted a memento of being thoroughly used. I was well on the way but rubbed at my bulge a little with the thought of what might come. I grabbed it deciding that it didn't have to be used in any event.

Right at seven I was standing at the door bags in hand. It opened and Richard gave me a deep kiss after ushering me in. "There's wine open and dinner is showing up at 8. You can go into the bedroom if you like when it arrives."

He poured me a glass of a delicious red and we sat on the small balcony and talked. He filled my glass often and I accused him jokingly of trying to get me drunk to take advantage of.

"I don't think I have to get you drunk do I. And yes I'm going to take thorough advantage of that lovely body and take that pussy again." He reached over and stroked my chest.

The conversation came easy. He had been married but his wife died of a stroke in his late 40's. They had no children. I expressed my condolences and there was a pause. "Have you always been interested in men too?"

I asked because my own journey to bisexuality had taken a long time.

"Not always. There was an interest and I also consider myself bisexual but since my wife died I've tended towards men. They're easier really. I can tell what they're thinking better and there's less complication. And I've always enjoyed anal and finding women who like it is tougher."

"Did your wife like anal?"

"How do you think I know how elastic a sphincter is? She enjoyed anal and I lucked out because I love it. Most women saw my size and hesitated even in their pussy. When I saw your reaction that's how I knew I had some work to do. Speaking of which, I have a question."

"Sure."

"We can do things two ways tonight. Making love or a nasty good old fashioned fucking. Should I guess?" I nodded wondering.

"I think you want to get fucked. Tell me what you want."

"Yeah" I said suddenly feeling shy and embarrassed. "I want some nasty, serious man sex."

"Glad to hear that. Dinner's going to be here in 20 minutes. I got some stuff for you earlier thinking it might go this way. Strip and go into the bedroom. And I saw you brought a camera. Bring it with you." His voice had a command sound to it right then and wouldn't have dreamed about arguing.

He opened two bags on the nightstand and tossed me a pair of red underwear I had to look twice at. They looked like normal boxer briefs but there was no seat. Just straps that took me a second to figure out and left the ass exposed.

"Show me how to use that camera. You look gorgeous in that." I set it for the lighting and showed him how to focus and shoot.

The other bag had a large glass butt plug.

"When I fuck you there's not going to be a lot of foreplay. I love ass pussy and I don't think you need any prep more than this after this morning. You can take it so get down on all fours and spread'em. You're going to wear this through dinner but first we'll get some pictures."

I got down and the underwear didn't prevent me from exposing my hole. I heard the shutter sound a couple of times.

"Here, get this wet." and he handed me the plug which I stuck in my mouth while feeling the lube drizzling into my pucker. He handed me the lube and then had me try to insert the smooth shape into my hole while he watched and took pictures.

"Better get that in. You know I'm bigger than that. Work on relaxing."

I squirmed because it was large, cold, and smooth but the tip wedged in and the rest followed as I grunted. Then he moved around my front and pushed that fantastic rod out the fly.

"Head is a good way to warm up although it's hard to come from it. I want some pictures."

I smelled the man musk and got a little hard myself but it was hard to open far enough. He had me look up into the lens as my cheek distended from the head.

"Those lips wrapped around me might even get me there. Not tonight but before the end of the weekend I'm going to spray that handsome face." Just then there was a knock at the room door and he tucked himself away and got it. Five minutes later he opened the bedroom door and we ate the steak and lobster along with working on another bottle of wine. He was completely dressed while I just had the underwear on while the plug made itself known each time I moved.

We finished desert and he looked at me with gleaming eyes. "Go assume the position again and get ready for a good hard fucking. I'll be in there in a moment."

I have to admit I got hard at the thought. My cock pushed at the underwear as I knelt and I dropped my shoulders to the mattress thinking of presenting most fully. I heard the door open and sort of wiggled in anticipation.

"Anxious little slut aren't you. You'll be biting the pillow soon enough. Get back on your hands because you're going to wanna brace yourself. Lube up my cock and do it good because I'm going to shoot the next lube you get up your ass."

He moved to my front and I slathered the thick, greasy gel on him. The erect flesh had veins that ran thick and bulging and the knob leaked fluid that would soon be in me. He moved away and the bed moved before my knees were nudged wider for height.

I moaned a little at the pressure of the plug being pulled but it came out to have the tip replaced with hot flesh. Hands grasped the top of my shoulders and almost instantly the pressure came and went at the shaft penetrated both muscles.

"Uhhhh" came involuntarily and I arched into him as he gave me no respite and went until his thighs hit my ass.

"You're broken in now as my bitch. Still a nice and tight pussy though. Well at least for us bigger folks." With that he pulled out almost all the way and hammered back in with a slap of flesh that rocked me forward.

"Play with yourself. I want you filling that pouch while I use your pussy." His hands left my shoulders and grasped my hips as I slid to my elbows and reach back down between my legs to grasp the hardness distending the front of the underwear.

"You're so warm inside. Like a hot bath." He was thrusting in and out with long strokes that almost exited and pulled at the flesh only to go balls deep. The sound of the coupling and our heavy breathing were the only noises and mine were getting louder as I couldn't help but respond to the rubbing of my package while that meaty cock stretched and distended my sensitive sheath.

"Ahhh" came from my lips as I couldn't hold out any longer and heard the streams of my cum splat against the fabric pouch while Robert gave me no pause as my muscles contracted around the thrusting meat.

"Yeah baby, cum with a cock in you. That's beautiful. I want you to cumming every time a cock is up you. I'm going to keep fucking you and when you can, do it again." He kept up the pace and although I was sensitive now, the lack of respite turned from sensitivity to hardness again.

"See, you're a sexy little slut. Every time you rub one out I want you to be thinking about my cock up you." He said all this in a low but resonant voice that gave me a little thrill and I went back to rubbing myself. The cum trapped in the underwear added lubrication to my messy crotch.

"This time baby I'm going to tell you to cum and when you do I'm going to put a load all the way up there. If you were a woman you'd be knocked up. Ready? One . . . Two . . . Three. Cum for me baby." He purposely slid in small movements across my gland.

And I did cum again to my surprise feeling the spurts hot against my skin under the fabric. At the first contraction Robert hilted himself and I could feel his balls moving against me. "Uhh, yeah take it up that beautiful pussy. Damn your tight mancunt is made for getting bred. "

Finished we stopped like that. Robert still firmly embedded as we sweated and I noticed the smell of lube, cum and musk of mansex. "Hand me that camera." I moved carefully and heard him turn it of and then the click. "Love the look of my cock stretching that hole."

I felt him start to pull out and the shutter clicked as he withdrew until I felt my hole gape without the fleshy intruder. "No doubt you lost your cherry. Makes me want to fuck you again and I will. Roll over now baby ."

I slipped down and rolled over to face him. He grabbed the waistband of the underwear and I raised up to let him pull them off. They were sodden in the front from my cum and he flipped them inside out to show the sticky mess.

He folded them so the sodden fabric displayed the couple of tablespoons of cum. Globules glowing bright white against the red. He reached out and put them just under my nose and I could smell the tangy bleach smell. "Put your tongue out and give it a lick. Then I want you to suck the fabric clean."

My tongue touched the cooling jism and I gave it a swipe. The fabric then met my lips and I had a mouthful. Slightly bitter and coating my mouth I sucked at the dampening fabric.

"Yeah baby, when you're with me I want you to always swallow all our juices with your mouth or this tight little pussy. That's right. When you're with me it's a pussy and my pussy." He twisted my legs and rolled me on my stomach and his hand delivered a sharp smack to my cheek. ". . . little hole that I'm going to fuck until nothing is left in my balls or yours. You ready to be my girly bitch?"

I still had a mouth full of fabric. Sucking the diminishing juices and feeling like a wanton, dirty little slut. He had me figured out and pulled the underwear from my mouth as I rolled to my side.

"Yes, I'm your girly bitch" I said panting from the physicality and the excitement of were he was taking me. Giving myself over completely and absolutely.

"Good. I'm going to send you home wet and open at the end of this weekend and next time I come up here we'll do it again. I think I'm going to have a lot more business up here."

He grabbed the glass plug and pulled my leg up so I was still on my side with legs sprawled wide for the lower half. It slid in easily and my hole sucked it up tight so the glass flange touched my cheeks.

Richard backed up and took a picture of my spread-legged invitation.

"Go get a warm washcloth to clean me up and then go shower and clean yourself except your pussy."

I got up gingerly as I felt the muscles ache and the plug kept itself seated. I was soon kneeling again and washed his juice and lube covered member until it was clean. I gave the head a kiss and it twitched upwards before getting up and going back to the bathroom for the shower.

Standing under the water there were waves of conflicting thoughts and guilt but also an underlying excitement. While it was not my first time having sex with a man it was perhaps the most submissive I had been. And that submissive streak showed itself in a blaze of hedonism and acceptance that I could take this role for these few days and own it. I turned off the water as the lust for what I was doing gave me a little shiver.

Drying off I went back to the bedroom where Richard sat in a chair reading wearing a robe. He looked up.

"Your clothes are in the bag there. Pick one and then let's have a glass of wine on the balcony."

It was a black, paper bag with script of a local high end boutique on it. Looking inside all I saw was folded lace. Pink, black, white.

I pulled them out and unfolded them on the bed. There were three identical sets in different colors. High cut with skimpy backs panties and short spaghetti strapped tops I think they call baby dolls.

Pink I thought. The dull ache in my backside made me feel feminine. I put my feet through the fabric and pulled them up. They weren't a thong but the coverage was just a two inch band that covered my crack. The top felt strange and must have been for a fairly small chested girl because my pectorals stretch the fabric. The bottom of it bisected my ass just below the center.

I must have colored and Richard noticed my embarrassment. "You're going to wear whatever I want when you're with me. I won't shame you but I want you thinking at every moment that you're my girl when we're together. Come sit on the balcony and we'll have some wine."

I edged out onto the open balcony nervous to be seen. A tall man wearing pink lace lingerie. The chair helped me be low enough that while I might be visible the darkness would help. Richard handed me a full wine glass and soon I was comfortable enough to talk. He kept my glass full as we ranged over topics that were incongruous with me wearing lingerie.

It was almost 11 o'clock when he urged me to lean over and grasp the stucco edge of the balcony. His fingers slid beneath the lace and tugged and turned the plug. "You're a hot little bitch aren't you. Just think, people from any of those rooms over there could look out and see you presenting your cunt to me. Inviting me to fuck you out here in front of everyone. Do you think you can keep quiet enough. I bet you can't. I love the way you moan and take cock but it isn't quiet is it?"

He removed his hand and tugged the panties down just below my cheeks before taking a harder grasp of the glass flange. He tugged and I could feel the thick bell spreading the sphincters while I puffed and tried to maintain silence.

My mouth went into an O as they gave and pushed the plug out with a start. There was no respite as he reversed and pushed at it and it slipped back in. "Uhhh . . . " came out with a little whine. Back and forth, fucking me with the plug as the cool air hit my face and I tried not to make noise and draw attention.

Then he stopped. "Everybody in the place was going to tell you were getting fucked. Somebody down there even looked up but I don't think they could see you. I guess we'll find out if they did. We're going to move on here before I put you away wet."

He moved away and sat in the chair with his robe gaping and that beautiful piece of meat pointing skyward. "Leave your panties down and take care of this."

I shuffled as best I could and knelt on the hard tile between his legs. His hands grabbed my head firmly as I lowered my mouth over the head. Although cocksucking wasn't my biggest turn on I found my saliva glands working overtime and the first bob left a shiny trail that I used to jack him with my hand.

Cheeks hollowed he guided my head up and down as I used my tongue to lave the underside. "I know you like cock up that pussy but a man likes his girl to polish his knob once in a while. I'm going to fuck you again soon but I'm going the shoot all over that pretty face. In a minute I want you to walk into the bedroom without touching those panties and lay on the bed and show me your pussy. Now give me a good suck and kiss the cock you need."

I bobbed up and down more until he pulled my head up. Then I gave that fat head kiss before standing and shuffling towards the bed. The options with the panties like were limited. I could roll on my knees, lay face down, lay on my back and pull my legs back as far as possible. I decided though to reenact how I lost my anal virginity and lay on my side, legs pulled back. I knew it opened me up for him for maximum penetration.

Richard came from the bathroom with a towel and when I saw him I pull the upper cheek wide to show him. "Yeah baby, show me that pussy. Let me get that out of the way." He reached over and I felt the plug leave my hole.

He handed me the lube bottle. "Finger your hole and get it wet for me. Put on a show."

I poured lube over my fingers while the other hand kept the crease wide. It wasn't hard at all for the lubed fingers to rub their payload on and then in. More lube then two and then three fingers coated the opening and worked the gel inside.