Becoming a Cuckold Ch. 03

"Oh, fuck!" I gasped, feeling as if my ass was being torn in two as the head pushed through the ring.

"Big, ain't it," Andre laughed. "Now you know how full your woman's pussy felt."

Andre was gentle; knowing how big he was. He didn't ram himself into my ass. He pushed, sliding inch by inch up my tortured passage.

"You like it yet?"

"No. How much more do I have to take."

"About two inches, more or less."

Please be less.

"This is good," Andre said. "Most faggots I fuck don't have assholes this tight."

Finally, I felt his balls smack against my cheeks. I remembered Mistress's first anal fucking, and I was glad I'd been gentle with her, remembered she'd taken six more cocks up her bum, including Shed's massive member, not quite as long as Andre was, but just as thick. Now that Andre was already in me, he bent down and started kissing me again. It felt stranger now, more like making love. Now his cock was buried in my ass.

I could feel my hard cock trapped between us, throbbing, Mistress not letting me cum for the last twenty-four hours plus. Andre started to move; three to four inches out, three to four inches in, my sphincter loosening from the pressure, becoming used to the thrusting, the foreign intruder.

I heard Mistress moan as she orgasmed. I looked and saw her fingers flying through her slit, enjoying her climax.

"Don't look at her; look at me," Andre ordered. "I'm fucking you. Now kiss me back."

I looked, and his eyes were watching me, watching my reactions, reading me. I kissed him back, our tongues tangling again. Andre sped up, fucking me harder, deeper, longer with each thrust. His prick was massaging my prostate with each lunge. I sensed the familiar tightening of my body prior to an orgasm. My balls tightening, my abs, the wonderful feeling of an orgasm about to happen. Andre felt my throbbing cock between us, the surging wetness, my groans of pleasure at my long delayed orgasm reaching fruition. Cumming not on his cock, but because of his cock, so deep inside me.

"Feels good, cuck boy. Finally getting to cum. That's it. Let go. Relax. Enjoy it."

He sped up, fucking faster, getting close to his own release, his tongue invading my mouth as he climaxed, throbbing his massive load in my ass, pulse after pulse. Finally still, breathing hard into my mouth. His cock finally shrinking, easing the pressure on my anal ring, sliding out on a wave of cum. Some air passed out at the same time, a fart fucked into my rectum with his pumping dick.

"Clean him up, Richard," Mistress said. "Suck him off until he cums down your throat. Show him what you've learned; what a good cocksucker you can be."

Surrender, obey, submit.

I began the process of trying to intentionally make a man orgasm in my mouth. Peter had been an accident, not paying attention to the signs of his arousal while watching Sven fuck my wife. I heard Cheryl gasp when his fat crown passed through my lips. The fact he'd just fucked my ass, making it more deviant, more dangerous, more lewd. Mistress made me lick and suck her strap-on after I've been cleansed, so the taste is familiar; the lube, the mucus, but different because of Andre's cum, thick on his shaft. I tried to remember all Beth had taught me about oral pleasure, all Mistress did to me when she seduced me with her mouth.

Searching for Andre's erogenous zones, his pleasure points, feeling him swell and grow again as I found them, played with them. When Andre was hard again, Mistress coming to me, her tongue dipping into my savaged flesh, licking the cum that spilled from my ass, digging her tongue inside, so soothing after his hard fucking, reminding me I was loved and cherished too.

Sometimes, I had all of his cock inside my throat, sometimes just circling the crown with my tongue, licking the sensitive spot below the glans where the head came together on the underside of his shaft. Sometimes, I lightly stroked the shaft while I rolled his balls in my mouth, sometimes one at a time, sometimes together. I licked behind his balls, the taint, the perineum, so close to the asshole Mistress would eventually make me fuck.

Mistress began stroking my cock with a lubed hand, while she drilled down my ass with her tongue, making me hard, making my cock twitch.

"I want you to cum when Andre floods your mouth with his jism," Mistress said.

I remembered Domina doing similar while she was whipping me, making me watch my wife suck Joshua's cock, telling me to cum when Mistress kissed me with his cum in her mouth, passing it to me. I moaned, thinking of it.

Mistress and I both recognized the signs of Andre's pending explosion. They were the same signs I exhibited every time I climaxed. His breathing grew faster and shallower, his cock started to swell, his balls drawing up. Mistress stroked me faster, harder.

Andre groaned and his cock thrust deeper, starting to throb, pulsing a jet of thick, salty-sweet, viscous, cum in my mouth. I gasped and shot my own load, pumping into her hand as Andre spurted into my mouth, flooding it, filling it, frantically swallowing it as he threatened to drown me in his cum. My own cum shooting across the floor, knowing I'd have to lick it up, clean up after myself.

I gulped, finally able to keep up as the flood slowed, the jets reduced to dribbles, still bubbling over my tongue, Mistress's hand slowing, squeezing out the last of my sperm. She kissed my neck, abandoning my bottom. I'm sure she got most of Andre's previous load. I could feel my sphincter closing, returning to normal.

"Do you think you'll puke again?" Mistress whispered.

I thought about it. Slightly queasy, but not bad, the cum I'd swallowed almost a lump in my stomach, probably imaginary on my part, no more than a tablespoon or three of the stuff, less than a quarter cup of cream.

"No, Mistress."

"That's good. Clean up your mess, starting with my hand."

"Yes, Mistress."

She fed me her hand, smeared with my discharge. I licked it clean, then found the drops of cum I'd expended past her hand, glittering on the tile floor. I licked it up. I looked at the other two women in the room, my witnesses. Both of them had shoved their hands down their panties and masturbated during my show. Their hands were still there, but immobile, merely soaking in the remnants of their own waves of pleasure.

"Damn, boy, you are one fine cocksucker," Andre said.

"He licks pussy even better because he enjoys it more," Mistress said, patting my head. "He's a very good boy." She stood up. "Why don't we take a break. Cheryl, if you help me make a tuna salad, we'll have that over lettuce for lunch and I'll crack open a bottle of wine. Domina, you might want to ask your brother about his new promotion. You'll be the first one we've told."

They got up and went to the kitchen.

"What promotion?" Domina asked.

"Mr. Thornhill asked me to be his personal assistant. I start learning my new job on Tuesday. Next Saturday, we have to be ready to move our things, what we take with us, Domina. Perhaps you'd like some of the things we don't need anymore."

"Where are you moving to? Please tell me it won't be too far away. I need to keep my eye on you."

"Manhattan, Central Park West, near his house, Domina."

"No fucking way?"

"Way. Job comes with the apartment, furniture, car, on top of the salary, Domina."

"How much?"

"Three hundred grand to start. More if it works out, Domina. It will involve a lot of travel. He said I'll need to go with him most of the places he goes."

"Are you talking about that billionaire guy, William Thornhill?" Andre asked.

"One and the same," I replied. "I guess I have more skills than just sucking your cock, Andre."

Andre laughed. "Are you going to be sucking his?"

"No. He's not interested in a male cocksucker."

"He should let you. For the amount of money he's going to be paying you, he should get his money's worth because you are a great cocksucker."

"Where does he compare?" Domina asked.

"One of the best I've ever had. Is the missus as good as you?"

"Probably better," I admitted. "She would get into it more than I would."

"You sure you don't get off on sucking cock?"

"Pretty sure. I do get off on being pleasing to my Mistress. She enjoys my obedience. I enjoy obeying."

"I could swear you were born with a dick in your mouth."

"Just training," Domina said, "from a very talented slave."

"You take the training too?"

"I was paying attention. She thought it might be useful to use on any lovers I took."

"Do you suck cock as good as he can, Ginger?"

"Maybe. I've never sucked one as big as yours, Andre, so it's hard to say. I assume Richard got some practice sucking yours before this morning getting you ready to fuck his Mistress. She told me you were spending the night last night."

"Maybe you need the practice."

"I'm thinking about it. I think I need a fucking more."

"Be glad to accommodate."

"We'll see. Richard needs more work first. I think you should sixty-nine, and I want to see him fuck your ass."

"Yeah, I ain't sucking him after he fuck my ass."

"No one's expecting you to. He took some enemas to clean himself out this morning," Mistress said. "It's the reason I shoved my tongue up his bum. I did it too. I think I need to feel your big cock up my ass as well as my cunt. I'll suck your cock afterwards while he licks my bum hole. Then, I expect you can sixty-nine for us. Lunch is ready. Would you pour wine, honey?"

"Yes, Mistress."

I poured wine while Cheryl and Mistress set the table. Three of us were still naked, Cheryl and Domina still clothed, though relaxed. Everyone had two glasses of wine, not going anywhere. It helped wash down some of the cum I'd swallowed.

Our meal finished, Mistress said, "It's time to get comfortable in the bed. Clean up the kitchen and join us when you're done."

I agreed and Domina stayed to help. As we cleaned up the dishes, she checked on how I was doing.

"Are you doing okay."

"As well as can be expected, Domina."

"Have you thought of using your safe word?"

"I've thought of it, Domina."

"Why haven't you?"

"Trying to surrender my ego, sublimate my will to Mistress. I figure the sooner I do so, the easier it will be in the long run, Domina."

"What's the scoop on your new job?"

"I can't discuss it with you with others present, Domina. My job entails keeping information regarding my employer confidential. I know I can trust you, but I don't know about the others. We can discuss it later."

"If it's any consolation, I wanted to tell you that watching you suck his big dick and get fucked in the ass was a great show. I couldn't help but masturbate to it."

"I wouldn't call it a consolation, but I'm glad you enjoyed yourself."

We went to the bedroom and Mistress was sucking Andre's rod, swallowing all of it as I had. With her smaller, shorter frame, and smaller face, every time she accepted his entire cock, a bulge in her throat appeared all the way to the hollow of her throat.

When I appeared, Andre moaned, "You're right. She is a better cocksucker."

Mistress pulled off his cock. "Like we did yesterday, honey. You and me in a sixty-nine with me on top, except I'm going to let this beautiful cock fill my booty."

"As you wish, Mistress."

Domina and Cheryl pulled up a couple chairs close to the bed so they could watch. Mistress got over me and she said to Andre, "Just soak your dick in my cunt. It should be plenty wet to shove in my ass."

"If you're sure."

"I'm sure."

I saw Andre fill my wife's pussy again, sliding easily inside her. She climaxed as he filled her, increasing her saturation, soaking his cock as she trembled through her orgasm. He gave it half a dozen more thrusts and adjusted his aim, going for the cute little pucker. Mistress groaned as he entered her.

"You're so fucking big. I love your big black cock, Andre. I could fuck it forever. You need to be a regular guest. Fuck me, fill me with your cum. Make me your ass slut."

Andre was giving her every inch of his cock on every thrust, from the crown until his prick was buried, his sack tea bagging my face as he fucked her. I concentrated on her clit, knowing every orgasm would ease the soreness created by his thick dick stretching her tiny butt hole. Apparently, I was doing a good job. Mistress was cumming fairly frequently, every three or four minutes, until Andre went rigid, his back bowed, flooding her back door with his jism. I could see every pulse pass through his prick, so close to my face.

In accordance with her plan, Mistress took care of cleaning his cock while squatting over my face so I was left with her gaping asshole. The rim was red and inflamed looking, horribly stretched by his fucking. Given how many times Andre had cum since he arrived, I was surprised by the amount of cum leaking from her ass. Apparently, his balls and prostate worked overtime during lunch to fill his sack again.

"Andre, please get over my husband in a sixty-nine and suck him off," Mistress said.

I was already in position. I didn't even have to move. For the second time today, I was faced with the prospect of sucking Andre to completion. The only difference was he'd be sucking me as well. Andre had no problems swallowing my cock. I wondered how many he'd had before me, if he preferred men or women or if he was indifferent to who he fucked.

Domina decided she was tired of just watching so she had Mistress lick her cunt while Andre and I fucked.

I was getting used to sucking his cock, not enjoying it, but getting accustomed to it being in my mouth. He'd cum more often and more recently than I had, so he lasted longer than I did. He swallowed all my cum and kept sucking while I finished him off, knowing I still had to fuck his ass. He got me hard again, and when I was ready, he pulled his legs back like I'd done, opening his body for me.

"I like to face my fuckers," Andre said, "know who's got their cock in my ass. I expect some loving, not a 'wham, bam, thank you, ma'am' type of operation."

I looked at Mistress and she nodded. I took some lube and greased myself up. Eying the snake which would be sliding between us, I put my cock at the portal to his muscular bum. I was about to ease it in when he said, "I'm going to fuck your wife later, slip my meat so deep inside her she's going to forget that little pecker of yours forever. You might want to think about that for a minute."

I did, less than a minute actually, then slammed my cock as hard as I could up his shitter.

He grunted. "That's right, cuck boy. I knew you had it in you. Fuck me hard, you bitch."

As I kissed him, I fucked him a new asshole. I felt his cock get hard between us, sliding between our bellies.

"You feel it, don't you? The big fucking dick I'm going to turn your wife into my bitch with. I'm going to put her ankles on her ears and fuck so hard and deep it's going to stick out of her mouth so she can suck it at the same time."

I started laughing and stopped fucking. "Did Mistress give you those lines because, no offense, those just don't sound like you at all."

"You don't think I can come up with that stuff myself?"

"No, I don't see you as the kind of asshole who gets off on running other people down. You're the kind of asshole who likes to get fucked in the asshole, but that's the whole point."

He grinned. "Busted."

"I'm thinking the whole face me while we're fucking and no 'wham, bam' was yours. The rest of it didn't sound like your script."

He looked at Mistress. "Sorry, I tried."

Mistress said, "It's okay. I was feeling a little sorry for saying all that stuff to him anyway. It seemed a little harsh. I just need him to be obedient, not feel bad about it afterward."

"He seems pretty obedient to me."

"He does to me too," Mistress said, patting my ass. "Go ahead, Richard, kiss the poor guy, give him some loving."

I resumed fucking him and I kissed him, right up until the time I spurted my cum up his ass.

"I'm going to take a shower with my husband," Mistress said when it was clear my orgasm was over, "then take him to bed, this bed. I need the rest of you to leave the room. Andre is going to be free the rest of the night, although I will need him again in the morning, so if either or both of you other ladies wants to feel what it's like to have that big cock in you, now's your chance. The spare bedroom is made up, the bed will sleep three if you're feeling kinky."

Turns out they were both feeling kinky, but that's another story. Mistress washed me, then took me to bed, sucked me erect and made love to me, riding me. Her cunt didn't feel that loose to me, though I didn't have the chance to fuck her ass, because we were both exhausted when we finished. Fucking is hard work. We fell asleep in each other's arms.

******

Mistress did fuck Andre again the next morning. He was in her cunt and I was in her ass sharing her body. I kind of liked Andre. Nice fellow. I even kissed him goodbye as you'll see in a minute.

Mistress gave him a thousand dollars as he prepared to leave later that morning. "Wait, you hired him, Mistress?. You hired a professional, a prostitute?"

"I prefer sex worker myself," Andre said, smiling. "Prostitute is so last century."

"I figured if he was a professional sex worker," Mistress said, "there'd be less chance of emotional complications. Keep it strictly business, you know."

"Speaking of that, I had a really great time," Andre said. "I'd like to do this again. You were lots of fun and I enjoyed myself."

"We can't afford to pay for sex all the time," Mistress said. "This was a one time thing."

"I'm not talking about hiring me. I'm talking about a date. Going out in my spare time."

"Does that mean this one is free," Mistress asked.

"I'd like to oblige but 40% of this goes to my bookers, and I do have to live. You got me kind of cheap anyway since you had me for two nights, but it sounded fun, and it was. I don't often get a couple with two other hotties thrown in. I have off nights where I'm not working, if you're not freaked out."

Mistress looked at me. I said, "Don't look at me, Mistress. You know I'm going to do what you want me to. Submit, surrender and obey."

"If we're not paying him, it's personal and there could be emotional issues which crop up?"

"You're talking about jealousy?"

"Among other things. He would be fucking your wife on a regular basis, no 'wham, bam, thank you, ma'am' sex."

"Do you plan on keeping me in submission and fucking other people, Mistress?"

"I do, but this would be different."

"Yes, and he'd also be fucking your husband, Mistress, so there's that. I'm not sure it isn't better to have one guy we kind of like and enjoy instead of depending on random fuckers we might detest."

"Give me your personal number, Andre, and let us think about this. We'll call you if we decide dating might be fun," Mistress said.

"I hope you call," Andre said, writing down his number on the back of a business card. "I had more fun than I usually do, and I really like you both. I'd like to see if I can't get Richard to enjoy sucking my cock since he's so damn good at it."

"Be careful, Mistress, if I do start to enjoy it, I might turn out to be the better cocksucker. You won't be better at anything. Cheryl already thinks I'm the better cunt licker."

"For someone who's doing this under protest, you have a pretty good attitude," Andre said.

"It's not protest really," I said. "It's learning to give up my ego, to forget the way I was raised with certain expectations and social conditioning. Plus, it's easier to laugh than to cry."

And that's when he kissed me, and I kissed him back. Surrender. He kissed Mistress too.

He said goodbye and left. We stopped by the spare bedroom. Cheryl and Domina were still asleep, cuddled naked together.