The Harder They Cum Ep. 03

Anna arrived right on time for Conner's second training session, delighted to be spending the afternoon with her lovely apprentice Siobhan and her sub. Anna and Siobhan had agreed to collaborate on Conner's training. More accurately, Anna wanted to watch Conner's transformation in close detail for her own voyeuristic enjoyment. That meant participating, and Anna was happy to make time in her schedule to foster this brand-new, Mistress-sub relationship. Anna felt her mission in life, if she had any at all, was to help as many men as she could become dedicated to providing themselves as a means to pleasure their female owners.

Shiv and Conner were not the first Domme-sub couple she had midwifed, but Shiv had become a genuine friend and a special relationship for Anna, who rarely mixed business with pleasure. Plus Anna liked breaking in novices, especially men who were being used by friends. Conner met her at the door, completely naked.

"How lovely Conner," Anna gushed, and stroked the palm of her hand down his chest onto his abs, careful to avoid stimulating his genitals directly. "Shiv told me you were becoming accustomed to being kept in the nude." Anna leered openly at Conner, from chest to groin. "So attractive, so enticing. Looks like the need to cover your assets is pretty much done with." Anna pressed her lips against Conner's ear. "Let's get started," she whispered dramatically.

Conner followed Anna into the living room, his eyes glued to her butt. Anna wore a form-fitting knit skirt that ended a few inches just south of her ass and accentuated every curve. She glanced over her shoulder to make sure Conner was appreciating her wardrobe choice. She noted Conner's stiff cock and smiled. Enticement was the first step to servitude, after all.

In the living room, Shiv was also dressed for the session in a skin-tight onesie that left nothing to the imagination. She might as well have spray-painted her body black. At five foot seven Siobhan liked to wear three-inch heels. She towered over most women and a lot of men.

Her height, combined with a muscular figure for a woman of her age intimidated a lot of men. Especially older men, locked into their dominant mind-sets. Shiv enjoyed upsetting their frail illusions, based on nothing but ill-conceived fantasies. Shiv knew she could replace their weak imaginings with something much more substantial. Anna was one of the few women she knew who shared her enjoyment in demonstrating how fragile male notions of dominance could be.

"Wow! Do you plan on making him wait at all?" Anna said. "Dressed like that's I'm surprised he isn't already ejaculating." Anna dropped her jacket and handbag in the middle the floor, then settled herself into the sofa beside Shiv. Siobhan waved Conner closer.

"Make yourself useful Conner. Hang Anna's jacket up and bring her bag here. Then I think she could use a good foot massage." The women watched Conner scurry to obey.

"He's a good sub," Siobhan observed. "He just needs to learn restraint. I wouldn't call him a premature ejaculator, but he really must learn how not to cum unless he has permission. I mean, how can I take him out to parties or trust him not to embarrass you when he's out with you? I'm hoping you can shed some light on this. Please tell me there's a work-around for this issue."

Conner knelt in front of Anna and carefully removed her stilettos. Naked, erect, already demonstrating much more subservience than he had in the previous session, Conner began massaging Anna's feet. Anna disliked nylons, so her feet were bare. Conner placed the soles of her feet on his warm thighs before moving on to her calves. Anna watched him thoughtfully before answering Shiv.

"He needs to stop thinking and trust that you will make it happen. Cumming is no longer his decision, consequently not his responsibility. He cums when he is told, period. His slut self will soon understand that rule and dictate the appropriate action to his cock. Well, it's actually your cock now, isn't it. But somehow he isn't quite there yet is he?" Anna smiled. "It's all in the finishing touches Shiv. After we are done training him he will squirt when you snap your fingers."

Anna reached into her handbag and pulled out a thick strap of black leather with a bright silver buckle on one end. She held the collar up for Siobhan's inspection. "He needs to wear this whenever he's in session Shiv. It is a symbol of his status and with repeated use, it will become a conditioned stimulus for sexual arousal."

Siobhan frowned. "Conditioned stimulus?" She repeated.

"It's a learning theory term. I use a lot of operant conditioning techniques in my work. Methods similar to those used in training animals other than men, like dogs for example. It means that the collar will become Conner's first tangible cue that he is about to be used like a rented mule," Anna laughed. "And it will eventually trigger a subconscious response, easily recognized by how fast Conner's cock hardens, regardless of how he feels or what he thinks."

Siobhan looked skeptically at the little belt. "Can he really become so conditioned that the mere sight of a leather collar will make him hard?"

"Trust me," Anna reassured her pupil, and dangled the collar in front of Conner's face. "It's not just any collar. It's his collar. After a few pairings he will start feeling horny as soon as he sees it, because he will know what's coming next." Anna leaned forward and slapped the end of the leather strap on Conner's cheek. "And he will be grateful to you for providing a clear demarcation of his boundaries, won't you Conner." She leaned back into her seat. "When it comes off, the session is over and he can resume his alias as your husband," Anna smiled slyly.

Without another word she bent forward and fastened the collar around Conner's neck. Passive, naked, erect and on his knees in front of the women, Anna tugged on the metal ring embedded in Conner's collar and they both watched his erection twitch, proving her point.

"The collar provides clear parameters for him and for you," Anna continued. "From the time you collar him to the time you remove it, Conner knows his place. When the collar is on, he is property. He becomes a sex tool that can be used by you or anyone you approve of, like me for instance," Anna grinned. She pushed Conner away with her foot then reached into her purse and pulled out a short chain leash. She clipped the leash to Conner's collar and pulled on it.

"Come along Conner, hands and knees, that's it. Let's go for a little walk." Anna led Conner down the hall into a spare room Shiv had renovated. It was a space where she could do what she wanted with her submissive husband. A safe place for her to express her more carnal self. She liked to think of the room as making space for her alter ego to flourish. Anna was the only other person she had told about the room.

"Hop up on the table Conner." Anna directed their man-pet onto a sturdy pet grooming table set low enough to allow easy access for the groomer. Conner took his place like a dog about to be groomed, or bred. Certainly like a sub, who had done this enough times to know exact what was expected of him.

Anna slapped the insides of Conner's thighs. "Wider, yes as wide as you can, good boy! Shiv, do we have something to secure his balls with?" Siobhan pulled a hair elastic from her ponytail. "This will work," she replied. "I've used them on him before."

Anna stretched the elastic around Conner's balls and weighed the bound package in her palm. "Nice. Handy too. Good thinking Shiv." Anna gave Conner's balls a condescending squeeze to get a corresponding grunt, then moved to the head of the table, assuming her role as head Mistress.

"Arch Conner. Shiv, can you begin priming our trainee for his next lesson please?" Siobhan pressed her palm down on the small of Conner's back and accentuated his arch. With her free hand she reached between his legs and found an already stiff cock.

"My goodness Conner, you must be looking forward to your pegging. Or are you just excited to see Anna again?" Siobhan looked mischievously at Anna. Teasing Conner was turning into one of her favourite pastimes these days.

"Butt plug?" Siobhan asked Anna casually, sliding her hand loosely back and forth along the length of Conner's stick. Conner moaned but held his position.

"You're call Shiv. We did promise to practise pegging while remaining hard. I don't want to disappoint Conner, but he's your sub. You know best."

Siobhan continued to entertain herself with Conner's stiff cock while she considered his immediate future, occasionally fondling the quivering elastic-bound ball sack. Conner moaned continually, distracting her.

"Anna, can you make him stop doing that please, I'm trying to think," Siobhan said, annoyed with Conner's disrespectful attitude, but continuing to play with her sub anyway.

Anna, obviously prepared for the opportunity, pulled a black rubber ball-gag out of nowhere and forced it snuggly into Conner's mouth, muffling his moans. She pulled the gag secure and buckled the restraining strap behind his head.

"No butt plug," Shiv decided. "He's a big boy now. Let's go right to pegging 101," she announced. "He's already hard and horny. I'm guessing there's no better time to get started." Siobhan retrieved a tube of lube while Anna tugged on Conner's leash, pulling his head up. Conner drooled around the ball gag but kept his pose while his wife lubbed his ass.

"He looks like he's on show. You know, like a dog show but for sluts. So a slut show I guess," Anna laughed. "Oh Shiv, take a picture of him please? It will be precious later, I'm sure."

"I'm actually filming this session," Siobhan replied. See the camera over there by the door? I'm recording everything. We can edit it later and zoom in on his more interesting responses. Keep him hard while I strap on the strap-on."

Siobhan left to get her dildo. Anna let Conner's leash dangle while she strolled back to the other end of the table. Her palm drifted casually over Conner's buttocks, the edge of her hand slid easily between his cheeks and her fingers found his tight, closed hole.

"Stay still Conner. You're about to get fucked. This is your first time isn't it? Are you an anal virgin Conner?" Conner made a muffled sound that might have been yes. Anna inserted two fingers into Conner's lubricated asshole and found his prostate. Her other hand took over where Shiv had left off, stroking the hypersensitive erection.

Conner desperately wanted to cum for Anna. He knew he shouldn't, but Anna was pumping him faster now, and working his hole. It seemed like she was deliberately making it difficult for him to obey. If he came without permission they would certainly punish him. They would probably spank him, then they might take turns fucking his ass. Conner's fantasies took their toll and before he could stop himself he blew his load in Anna's hand. He heard Anna chuckle quietly to herself.

Siobhan walked into the room just in time to see Conner splatter cum all over the massage table. She was speechless. Almost.

"Conner! What have you done? Anna, did you give him permission?" Anna shook her head sadly.

"Looks like your sub could use some discipline Shiv. I see you found your strap-on." The thick latex dong protruded from Siobhan's crotch and bounced slightly as she strode to the table.

"SMACK!" The sound of Siobhan's open hand striking Conner's ass echoed through the room. Conner flinched but remained anchored on all fours, ass extended.

"I will deal with your disobedience later. But I will not allow your inability to follow instructions spoil my plans today." Siobhan stood facing her husband's raised rear end. "Ass up, and on your elbows," she snapped, clearly annoyed. "Shuffle back towards me where I can reach you." With one hand on Conner's raised butt she positioned the head of the dildo against his hole.

Anna strolled back to Conner's head and cupped his chin in her palm.

"Tisk tisk Conner. What a bad boy you have been," Anna grinned. "If you can't wait for permission what good are you? We can't have a sub spewing his spunk all over whenever he feels like it." Anna slapped Conner's face playfully.

"Shiv, I think we may have to cage him until he learns to hold his urges in check," Anna said, just as Shiv eased the head of the fake cock into Conner's tight hole.

Conner made garbled noises and clenched his buttocks. Another sharp slap on the ass relaxed his butt and Shiv pushed the rest of the nine-inch dildo into his well-lubed hole. Conner moaned then began to cry softly.

"It's Ok, Anna assured Shiv. They all react a little differently to the strap-on," He's not in pain, he's just giving up his manhood. Being the recipient of the cock tends to drive home the point that his ass belongs to you now." Anna wiped the drool escaping from Conner's opened mouth and patted his face.

"Good boy Conner. Just relax. Your ass is growing accustomed to the dildo. With practise you will learn to accept anal toys and even beg for some of them. Before we are through you will be a pro at surrendering your body. Some subs even come to crave the strap-on, it's such a symbolic act of submission."

Conner groaned with relief as Siobhan withdrew the long thick prosthetic penis, then grunted as she scewered his ass again. Shiv's thighs slapped rhythmically against Conner's ass cheeks as she picked up the pace.

"Faster Shiv," Anna directed. "He needs to feel like you mean it. Being fucked from behind by the woman who wins him will give him the confidence to behave like the sub-slut he is."

Siobhan held Conner's ass in both hands and rode him like she expected the fake cock to erupt. True to his nature, Conner fucked back, pushing his ass against Shiv and grunting with every thrust.

Watching Shiv peg Conner made Anna a little horny herself. She undid Conner's gag and popped the rubber ball out. Anna hiked up her short skirt and positioned her pussy above Conner's head.

"I'm going to squat in front of your face Conner. I want you to inch forward until you can lick my pussy from top to bottom and back again, Understand?"

"Yes Ma'am," Conner replied and stretched to bury his face between Anna's open legs. Anna's bare crotch felt warm on his face. She held Conner's head in place by grabbing handfuls of his hair. He lapped at the wet slit until Anna moaned and began grinding her pussy into Conner's mouth.

Anna used Conner enough to feel satisfied then straightened her legs. On impulse, she leaned forward and with her hands braced on Conner's bare back, kissed Siobhan on the lips. She found herself in a very calm place where everything seemed right with the world. Anna smiled.

"Done yet?" She asked.

"How would I know?" Siobhan replied, a little out of breath, but still pumping her man-cunt. Anna leaned her weight forward onto her arms with her face inches away from her protégés'.

"If you're satisfied, you're done," she said, and kissed her lightly again. "You're very beautiful Shiv. Don't worry I'm not interested in having sex with you." Anna smiled. "Well, at least not only you. But that's not why I'm here." Anna straightened up. Shiv slid her cock into Conner one last time and slapped his ass.

"Get used to it sub. I like the feeling of empowerment so we'll be doing a lot of this." Conner gasped as the dildo was pulled out of his hole.

Within minutes of having his fuck-hole vacated, Conner felt Anna's fingers forcing his semi-erect cock and balls through a metal ring. His flaccid cock was then forced into a small, downward-curved wire cage. The cage was fitted onto the ring and locked with a small padlock. Anna held the key out to Siobhan.

"He'll need to be kept on a tight leash," she warned. "Keep him locked up most of the time with supervised time out. He must not be allowed to play with himself. As I mentioned, Conner should be allowed to cum when it suits you. It is a privilege now, contingent on good behaviour, not an inherent right." Anna cupped Conner's exposed balls and patted his ass, still on display.

"Bye bye till next time. Can you walk me out Shiv? Some instructions are better for subs not to know." Anna and Siobhan left Conner on the table. Naked and caged, he waited on his elbows and knees for Shiv to return. He was ashamed of what he was becoming. But he stayed on the table, unable to move until she came back to take his collar off and end the session.