Surprising Relationship Evolutions Ch. 02

As he slowly worked his mouth back to her sex, she looked over and saw the older woman regarding her and smiling comfortingly.

Keisha didn't know why she felt the need to confess, "I've heard about it, but I haven't been with anyone who went down on me before."

The woman spoke reassuringly, "Well, you have won the lottery, then. I've had many, and Connor is the best I have ever experienced. Enjoy it."

The man slid his body between her legs, and leaned up so that she could feel his breath on her moist center. Keisha drew in a breath waiting for what came next.

Connor opened his mouth wide enough that he covered her entire mons. He used his lips to gently caress her, while using his tongue to lightly trace her labia.

Keisha whispered, "Ohhh fuck me..."

In response, he did, pressing his tongue into her body and fucking her with it.

"Mmmm... oooooh."

He grasped her buttocks with both hands, in part to support her, in part to support himself. He danced his tongue over her nether lips for a bit, then went in for "the kill."

"Oh, gawwwwd!"

She felt his soft tongue bathing her clit, then he seemed to change his tongue to a point and begin lashing her bud from all directions.

She instinctively grasped his head in both hands as orgasms, possibly the most intense she had ever experienced, coursed through her body. She was crying out and thanking him, and her maker.

Keisha's legs were trembling, and she was reconsidering her decision to remain standing. The Country girl sensed this, and Keisha let the woman guide the man onto his back on the floor, and her onto her knees over his face.

Keisha figured it was about over, but soon discovered the ride had only begun.

The white boy suckled on her thighs and the outer edges of her sex... it felt good, so she remained in place, even though she knew she should be getting back to work.

But then it went from feeling good to a rising arousal. She felt herself building towards another series of orgasms.

And then, as if he could feel what she was feeling, he returned his focus to her sensitive bud.

"Oh my fucking gawd..."

The older woman and the Country girl both grinned at her as if they knew what was happening.

The older woman said, "Hold on little girl. It's kind of a challenge for him."

Country girl added, "He will make you cum til you can't take it anymore... you will have to tell him when to stop."

As Keisha was moaning through another series of climactic releases, Connor was trying to deal with his lack of release. He did not even know this young woman, yet somehow her latent eroticism had his manhood straining more than ever for an orgasm it could not have. It made him want to make her cum all the more.

During one of the between orgasm periods, Keisha's phone buzzed. Bobbie looked at it for her and read the text, "It looks like your boss is wondering why this delivery is taking so long..."

Keisha responded, "Te-tell him to fuck off!"

Bobbie, not in the midst of orgasmic bliss, typed into the phone, "Car trouble. The nice man here is looking under my hood and working it. Back soon..."

"Working it?"

"Oh, yeah. He knows what he is doing. Should be up and running soon."

"Okay. Let me know when you're coming."

"Yes, sir!"

Keisha was young... and vibrant... and full of sexual need. Connor took her over the top at least ten times before she could take no more and fell beside him in exhaustion.

"Motherfucker! Son of a fucking bitch! I love you, you fucking bastard!" She said this as she attempted to catch her breath.

Once she had, Kathleen gave her a bottle of water, and gave her ex a beer. They sat chatting for awhile, and soon Keisha knew the dynamic she had walked in to.

Keisha asked, "So, he doesn't belong to either of ya'll?"

Sensing where this was going, Bobbie laughed, "I suppose he BELONGS to both of us and neither of us... would you like his number?"

Keisha nodded, embarrassed. Bobbie motioned for her phone, and typed Connor's info into it without asking him. "Just remember, I've got first dibs on his tongue."

Kathleen spoke up, only half joking, "Hey!"

After Keisha left, they had their dinner, and the girls flipped a coin to determine who got to be Connor's dessert. Then they took turns keeping him busy as they watched movies late into the night.

By the end of the night, they put him into a freezing cold shower to try and reduce his shaft inside the cage. His manhood was discolored and pressing itself through the vent holes. He needed some kind of relief.

Bobbie volunteered to sleep on the couch if they could put Connor in the guest bedroom. He thought this meant some relief, until they took turns waking him during the night for servicing.

They did let him sleep in Sunday morning, partly so they could also.

After enjoying breakfast that he prepared, they guided him to the bedroom. Again they flipped a coin. Bobbie won.

She lay on her back on the bed, and directed Connor atop of her in the missionary position. She guided his caged manhood into her sex to the extent it would enter.

Behind him, Kathleen slowly inserted the wand Vivian had given her into his backside, and with some exploration, began to massage his prostate.

Suckling on Bobbie's breasts, he moaned at the unfamiliar sensations from his prostate. It felt good. Then after several minutes, he felt his seed forcing its way very slowly through his urethra, without the satisfaction of an orgasm.

The odd sensation continued for a long time. Then, when he stopped moaning, Kathleen discontinued her manipulation of his ass and lay back.

Bobbie dislodged herself from his imprisoned manhood and moved to his face. Sitting on his face, she pressed her tummy to release the copious amounts of semen he had filled her with into his mouth.

The eroticism he felt was multiplied by the realization that he was consuming his own cum while she experienced multiple orgasms from his tongue.

Humiliation compounded upon humiliation upon frustration from near constant arousal without relief.

And he was loving every minute of it.

The following week the girls tried the same gambit. Bobbie even refused to try her keys until they were at Kathleen's house, building the anticipation for both her and Connor.

None of the keys worked!

It was going to be another long weekend of torment and oral servitude with no relief. Things got worse... or better, depending on your viewpoint.

Bobbie had commented that she was really missing dick. Kathleen smirked and said she could help if Bobbie was interested. She disappeared into the bedroom and returned a few minutes later, wearing only a large, heavily veined, bulbous headed dildo in a strap-on harness.

Bobbie's eyes grew wide, "Oh, fuck me."

Kathleen giggled, "That's the idea..."

Bobbie did not have to be told twice. She dragged Connor to the master bedroom and pushed him onto his back on the bed. She climbed on top of him in the sixty-nine position, presenting her backside to Kathleen and her phallus.

Kathleen commented, "I see we won't need any lube..."

Connor had a close up view, his face only inches away from Bobbie's snatch, positioned between her thighs. He watched in amazement as his ex-wife every so slowly pressed the huge shaft into his work-wife / girlfriend's sopping wet pussy.

As the pseudo cock disappeared, stretching the sheath it occupied, Bobbie moaned with pleasure, Kathleen sighed with domineering satisfaction, and Connor groaned in frustration, his manhood desperately trying to harden.

Bobbie was trembling as she was filled up. When the shaft had completely disappeared within her body, she convulsed. Kathleen remained still while the younger woman gyrated and pressed back, adjusting herself to the girth and the fullness it provided.

Bobbie leaned her head down to look towards her thighs and Connor's face. She had an ornery grin, "Barbie's dick is much bigger than yours... even if you weren't locked up..."

She shifted her hips and encouraged Kathleen, "FUCK me."

His ex needed no more encouragement. It was if she had something to prove. She wanted to make little work-wife beg for HER, and make Connor want her. Having to compete for his attention made her want retribution.

As a result her all out assault on Bobbie's cunt was highly motivated. She wanted to make this little bitch cum hard, and she wanted to leave her barely able to sit for a week.

She accomplished both. Soon Bobbie was screaming in desperation as waves of orgasms crashed through her. Her head down, she bit the inside of Connor's left thigh, dug all of her fingernails into his ass cheeks and held on for dear life. She was completely unconscious of any pain she was causing him; but it was okay because so was he.

All he could think about was how much he wished it was him fucking the hell out of one of them. He was trembling with unrequited need.

Kathleen continued hammering the big phallus into Bobbie, harder and longer than she would normally have strength and stamina for, but she was mindlessly driven.

The ecstatic assault did not end until, through the fog of her own orgasms, she finally realized Bobbie was begging her to stop. She relented and fell back onto her haunches.

Saturday, the ladies in Connor's life both felt they needed a break from sex, but had no intention of giving Connor one. So they ordered pizza, specifically requesting Keisha.

Keisha was smiling ear to ear when Connor opened the door, nude but for his cage.

Kathleen and Bobbie relaxed, watched a movie and ate pizza while Keisha joyfully rode Connor's face to ecstatic release.

As she left, she reached up and kissed him, tasting herself on his lips, "Thank you so much for the tip."

Sunday afternoon, Kathleen had another devious torment for her ex.

This time she placed the strap-on harness onto him, and he realized it had a space for his caged cock below the larger dildo. Now he had a big useful penis mounted just above his caged useless one.

Kathleen directed him to lay on his back on her bed. She then sat astride him cowgirl style, and gently slid herself down onto his pseudo-cock. She then giggled and invited Bobbie to mount his face.

They both knew what they were doing. Their primary focus was their own satisfaction, but they were also eager to increase his torment even more in the process.

Bobbie thought about sitting facing Kathleen so she could watch her fucking herself on the dildo. But she knew the effect her breasts had on Connor. So she sat facing his feet. That was while he serviced her, he would have a view of the bottom of her jiggling globes.

Kathleen was just as devious. She began with slow gyrations, enjoying the sensations on her G-spot, but also making sure her bountiful ass was knocking Connor's real manhood about.

Eventually she was needing more and did not "spare the horse" as she began pounding herself down upon the dildo violently, crying out in the pleasure of it. The motions bounced his caged cock vigorously, providing just enough sensations to drive him crazy, not enough to let him cum.

He became distracted, staring at the bottoms of Bobbie's perfectly pert breasts and moaning. His member was desperately attempting to burst out of its prison. It was a good thing he was not wearing a cheap plastic model. She quickly grasped his head in both hands and pulled him back into her crotch to remind him of his duties. He needed no more coaxing and began lashing her clitoris lovingly.

Kathleen was set off first. "Oh fucking shit!"

She was blind in her release. She cried out and reached out, grabbing hold of the first thing she found for purchase while she slammed even harder on the fake cock.

Connor's junk was bouncing up and down in a tantric rhythm... if his cock had not been so inflated it would have crashed repeatedly against the inside of the cage.

What Kathleen inadvertently latched onto for dear life was Bobbie's heaving breasts from behind. Her hands covered them completely, squeezing them hard and pinching her erect nipples.

The eroticism of the entire event, the pleasure pain of her lover's ex seemingly trying to rip her tits off, and Connor's tongue lashing her bud was just too much. Bobbie interlaced her fingers in his hair a screamed as orgasms tore through her, and she fucked his face with abandon.

Poor Connor was on such a tremendous overload. His compressed cock was pulsing... he thought he might actually cum despite his imprisonment. It was not to be. He just quivered uncontrollably with need.

Soon they were all three laying on the bed together in a sweaty mass... two shaking with release, one with frustration.

The weeks seemed to be getting longer for Connor. The only saving grace was that work was very busy, so at least there he had something to take his mind off of his need.

At least most of the time. His Tuesday therapy session had gone well, although after an extended cunniligus session for Vivian, she'd had to ice him down to get him back into his cage.

Wednesday he stood at the podium in the briefing room, explaining background, routes and details for a pending raid on one of his suspects. Everyone else was sitting at tables facing him.

Except for Bobbie. Bobbie was leaning against the wall in the back of the room, watching him.

When she was certain he had everyone's undivided attention, because he was describing entry points into the residence, she grinned.

She slowly unzipped her raid jacket, revealing that she wore nothing beneath it. She pulled both sides away to display her bare, perfectly pert breasts to him.

Both of which still bore dark purple bruises in the shape of his ex-wife's hands.

"Frank and Tommy, you'll take the back... unnghh..." His manhood suddenly attempted an escape from its prison. His eyes were focused on Bobbie.

Everyone spun around to see what he was looking at. But she had already zipped her jacket and stood there innocently sucking the straw on her soda.

Bobbie found ways to tease him throughout the week. Thursday night she had to check on her mother, so Connor thought he was going to have a relaxing evening at home with no sexual torment.

At about six o'clock his doorbell rang. He opened the door to find Keisha standing there with a pizza Bobbie had ordered for him. She had that beautiful smile, "Bobbie said you would provide your usual tip."

Now she had his address. Connor would become accustomed to free pizza.

Friday night he was standing naked in the living room of his former house before Kathleen and Bobbie again.

Kathleen had the strap-on sitting on the coffee table, prepared for another failed prison break.

She tried her first key, and the first lock popped open. She left the padlock in place, since they did not really expect to be able to unlock the second. Her second key had no joy.

Bobbie tried her first key. It refused to turn the lock. She sighed and tried her second key resignedly.

It turned, and the hasp popped open.

There was complete silence in the room for at least a minute as all three of them stared in disbelief at both open padlocks hanging from the device.

As he thought about what was to cum, Connor's penis tried to break free. If the hasps had not still been in place, it would have pushed the tube away from the ring around his balls. He was growing more and more excited, his breathing somewhat ragged.

Kathleen picked up the large dildo with the impressive veins and flared head, regarding it. Then she regarded Connor's manhood, remembering how impressive it was, how good it felt. Still, it was not as large as the fake phallus.

Without a word, she looked into Connor's eyes, and snapped the padlock she had unlocked back shut with a "snick."

He held his breath. She couldn't be serious. Surely she was just fucking with him.

Kathleen stood and began fastening the strap-on around her waist, looking at Bobbie lasciviously.

His work-wife/girlfriend arched an eyebrow, then without even looking at his desperately needy cock, reached over and pressed the other padlock shut, "snick."

The two women stared at each other and Bobbie spoke, "Damn I need your big dick, Barbie."

Connor looked from one woman to the other and back again in disbelief.

It had been fairly easy for him to maintain his composure when his erection was bobbing in the air while he serviced Vivian. She was a lesbian, and made it clear his penis would not be the first to enter her sex.

It had been pretty easy for him to keep his cool through all of the sexual activity with his ex and his girlfriend, and the pizza girl. Yes, it had occurred to him to cut the locks, but that would be cheating.

Besides, he had devoutly practiced stoicism his entire adult life.

Nonetheless, the thought of being forced to watch them enjoy themselves without him when he COULD be freed, after being denied for so long, pushed him over the edge.

He lost it.

Dropping to his knees, tears in his eyes, he wrapped one arm around Bobbie's waist and the other around Kathleen's. The pseudo-cock pressed against his face.

"Please! Oh, gawd, please!?"

They both looked down at him in surprise.

Kathleen asked, "Are you actually..."

Bobbie finished the question, "...BEGGING?"

"YES! Yes, please, please I need you!"

Both women looked at each and smiled. Then they high-fived each other.

Kathleen shouted, "It worked! We win!"

Connor looked up at them questioningly, confused.

Bobbie placed a hand on his head tenderly and responded to the unasked question, "Baby, you just had a break through. You wanted someone to make you beg... we knew you would have no reason to if we simply freed you when we could."

"You mean?"

Kathleen was already unfastening the harness from around her waist. She held the dildo in her hand, "Yeah, buddy... this thing is good to play with, but it doesn't hold a candle to YOU."

Bobbie tugged at his arm, "Stand up so we can get that thing off of you..."

They both quickly unlocked the padlocks and removed them. It was not necessary, but for symbolism they both wriggled the cage from his growing shaft. Then they would together to wrangle the retaining ring from behind his testicles.

Connor stood there with his manhood hard as steel, dripping pre-cum. He looked at both women, who were also nude. Both had erect nipples and moisture glistened from their labia.

Kathleen spoke, "Now you just have to decide which one of us you want first... who do you want most?"

He could not speak.

Bobbie placed both fists on her hips, "Well??"

After a moment both women doubled over in laughter.

His ex pointed at him, "You should see the look on your face!"

His work-wife snorted, "That, Kat, is what we country girls call a deer-in-the-headlights look!"

When they had recovered, they decided how they would choose who got laid first. They were going to flip a coin, but then Kathleen suggested something else.

She retrieved a tube of lipstick and they both applied it to their lips. She spoke, whoever leaves a ring furthest down on his pecker, gets it first."

She knelt down before him and took him into her mouth she gagged and shifted her throat, going down as far as she could. When she finally let up, there was a lipstick ring almost to the bottom of his shaft. "Ha! beat... cough... that!"

Connor was already afraid he would lose it when Bobbie knelt down in front of him. She made a theatrical production out of stretching her neck and her mouth as if prepping for an athletic event. Then she engulfed him and with only a little effort, slid his phallus all the way down her throat. Her lipstick ring actually touched his abdomen. She loved giving head, and had lots of practice. She felt his shaft pulse, and quickly rose off of him before he could cum. She actually craved his seed, but blast by BJ wasn't the deal.