The first session. Part 3

Please read part 1 and part 2 before reading this.

2 Hours later, they both stopped, switched off the vibrators attacking his feet and armpits, and Caitlyn removed the gag and blindfold.

Nathan, shattered and broken to the point where he couldn’t even form thoughts, barely even conscious, just sat there staring into space, his head spinning, psychically and mentally exhausted beyond belief.

The 2 mistresses stopped their assault on his body, and just stayed with him, gently cuddling and comforting him.

After a few minutes, Nathan, having regained his breath and some of his mental capacity, didn’t say anything, just started sobbing profusely.

“Shhhh, it’s ok baby,” Whispered Sandra in a soft and comforting voice, wiping away Nathan’s tears. “The tickling's over baby. All done.”

They continued to cuddle and comfort him for the next 15 minutes or so while he calmed down.

They untied him from the chair and, with great effort, between the 2 of them, they managed to pick up the zombified Nathan, and carry him to the table a few feet across the room.

“We're gonna make you feel real good now baby.” Sandra whispered, as they both proceeded to tie him down again.

Caitlyn moved the cart that was still next to the chair over to the table, pulled down Nathan’s now sweat soaked thong he had come in, took the bottle of oil, and generously applied it to his cock, while Sandra continued rubbing and comforting him.

“OK slave,” Caitlyn said. “We’re going to pleasure you now, but you aren’t allowed to cum until we give you permission. If you cum before we say so, we'll tickle you for another 2 hours. Do you understand?”

She got no response.

“I’ll take that as a yes,” she said, as she began to stroke his now rock hard cock.

Sandra began running her tongue up and down his neck, softly whispering into his ear while lightly nipping it.

Slowly beginning to come to his senses, Nathan started to realize what was happening, “feels good,” he weakly thought.

Sandra moved away from his neck, and down to his nipples, teasing one with her mouth and tongue, and gently pinching and twirling the other one.

As his heart rate shot up, Nathan weakly and softly, started to groan with pleasure.

Both mistresses immediately stopped what they were doing. Nathan whimpered slightly in protest. “Good boy,” Caitlyn said. “We won’t be able to savor the moment if you cum too fast.”

“There's still a LOT more fun for us to have, baby,” Sandra said innocently. “You wouldn’t want to spoil it, would you?”

Nathan still couldn’t find the strength to answer, now starting to become aware of his surroundings and what they were saying.

After giving Nathan a few minutes to cool down, they repeated the process twice more. With each time Nathan grew increasingly more frustrated.

“OK! I think it’s time we move on to the next event,” Caitlyn said with a smile, reaching for the bottle of oil.

“My throat is really parched,” she continued. “I could really go for a glass of milk right now!”

With a grin on her face, Sandra whispered into Nathan’s ear. “You hear that baby? She's gonna milk you.”

Despite his intense nervousness, as he was a complete ass virgin, never so much as even having a finger inside of him, Nathan felt his dick shoot up to an even more erect state, a bittersweet feeling of arousal and fear washing over him.

He couldn’t find the energy to protest yet, so he just groaned weakly.

Caitlyn smiled at him and asked, “have you ever had your man pussy milked before, slave?”

Still too weak to speak, but now conscious of what she said, he defeatedly shook his head slightly.

“Ooh, we got a virgin!” Sandra teased. “Don’t worry, you’ll love it baby!” She said, continuing to rub his nipples.

“Every man secretly wants this,” Caitlyn said as she squirted some oil into her hand and gently applied it to Nathan’s freshly shaven ass.

Nathan jumped from the slight coldness of the oil and the unfamiliar feeling of having someone touch his ass.

“Don’t be scared baby,” Sandra said. “She’s a professional, she knows what she's doing.” Her words did help, somewhat, in calming Nathan’s nerves.

Nathan softly groaned, as he felt Caitlyn slowly insert her left middle finger into his ass. It was a strange, somewhat uncomfortable feeling, but the tired Nathan realized he didn’t dislike it, in fact, he found that he actually quite enjoyed it.

“See, feels good doesn’t it baby,” Sandra said, as she continued to play with his nipples, her fingers twisting and twirling his right, while her tongue went to work on his left. “She's had a lot of practice. I can tell you from experience that her fingers are heaven.”

Nathan jumped as he felt Caitlyn flex her finger upward inside of him, in what he could only describe as a “come hither” motion. He felt a strange, familiar yet exotic pressure deep inside his lower abdomen and pelvis area.

Caitlyn smiled. “The prostate is one of the most sensitive parts of a man,” she said. “When it’s stimulated…”

She pushed harder upward, toward his dick, causing Nathan to jump and moan at the sudden, unexpected sensation.

“They lose all sense of control.”

She continued to quite aggressively massage his prostate, at first varying every few seconds between a left to right, and an up and down motion, before finally settling on a sort of circular motion..

After a few minutes of constant attention to his ass from Caitlyn, Nathan began to feel what he thought was an orgasm build.

“Ah, I’m gonna cum,” he thought to himself. He moaned and felt warm, creamy fluid pour from his dick, but the intense pleasure he was used to, never came.

Confused, he tried to crane his neck forward to try and get a view of what had happened, but he failed, still too tired.

“I-I came didn’t I?” He thought to himself. “Why am I still so horny?”

Caitlyn, upon seeing the confused look on his face, smiled at him, and said, “if you’ve never had someone play with your ass, you’re probably confused as to what happened. Basically, think of it as me massaging the fluid out of your prostate, without letting you cum. Oh but don’t worry, it definitely is possible to cum from your man pussy! We’ll get to that later though.”

Desperate to cum as he felt his rock hard cock twitch, the increased blood flow to it, starting to become slightly painful.

Finally finding the energy to speak, he weakly and quietly pleaded, “p-please let me cum. Please touch my dick.”

Caitlyn smiled contently at him. “Not yet slave, you’ve still got a lot of fluid in there that I need to milk out of you.” She said happily.

After receiving 2 more milkings until his prostate was completely empty, Nathan, hornier than he had ever been in his life, his cock twitching uncontrollably, desperately pleaded again.

“Please let me cum Mistress! Please!” Caitlyn sighed as she looked at him, seeing the desperate look in his eyes. “Ok slave. We can move onto the main event now,” she said.

Nathan, feeling a string of hope rush over him, naively thinking she was going to touch his penis, said, “y-yes. Thank you Mistress. Please let me cum.”

Caitlyn smiled sadistically at him, reaching into the cart and pulling out the strap-on that he had asked for the other day.

“OH FUCK!” Nathan thought to himself, only just now remembering what he had asked for in the interview.

Caitlyn, upon seeing his shocked face, smiled, and innocently asked, “what's wrong slave? You asked for this, remember?”

“That's right!” Sandra said. “And we always try our best to satisfy our clients.”

Caitlyn removed her drenched panties and teasingly rubbed them on his face.

“You feel how wet these are slave?“ This means you did a good job pleasing us today,” she said, placing them over his face so that he could feel the wetness on his skin.

Caitlyn grabbed the strap-on and put it on.

She grabbed the bottle of oil and generously coated the strap-on with it.

“W-w-wait,” Nathan stammered weakly still. “I don’t think that's a good idea! How about yo-MFH,” he said, having been cut off by Sandra’s panties being shoved into his mouth, which she had started to take off as soon as he began stammering.

“That’s better,” she said, climbing onto the table and placing her sopping wet pussy directly over Nathan’s face.

Even with Caitlyn’s panties partially covering his eyes, he still got a great view of it. Freshly shaven, bright pink and soaking wet from the constant state of arousal she had been in for the past few hours. He could feel droplets occasionally land on his face.

“Enjoying the view baby?” She asked sweetly. “If you do a good job…” she reached down and removed her panties from his mouth, placing them instead on top of his rock hard cock. “We might just let you cum,” she continued, lowering herself down with her thighs so he could access it with his tongue.

Nathan immediately broke again, gave in to his sexual urges, and began vigorously, kissing, licking and sucking her, pushing his tongue as far inside as he could.

“O-oh,” Sandra said, her head rocking back slightly in pleasure. “Someones eager.”

With the sight of her girlfriend's pussy being ravished by someone other than her, Caitlyn began to feel an ache, come from, deep inside of her, and, admittedly, grew slightly jealous, wishing desperately that it was her underneath Sandra.

Noticing that the lube in his ass had started to dry, she picked up the bottle of oil for a final time, squeezed some into her hand, and gently reapplied it.

She stepped back, admiring the view a moment longer.

“Are you ready slave?” She asked.

Nathan, too lost in the admiration of Sandra’s pussy, didn’t hear, and, even if he had heard, his mouth would have been too busy to answer.

“I’ll take that as a yes,” Caitlyn smiled.

Caitlyn placed her hands on Nathan’s hips, and gently inserted the tip of the strap-on into him, taking care not to be too rough so as to cause pain. Though she would happily tickle torture anyone who asked to the point of breaking with a smile on her face, pain wasn’t her thing, not physical pain at least.

“Oooh,” Nathan moaned as he felt the strap-on slide inside him, briefly stopping the attention he was giving to Sandra.

“Hey, who told you to stop?!” Sandra said, reaching forward and giving both of his nipples a hard pinch. “Keep going.”

He obliged, continuing to pleasure her pussy in between moans. Caitlyn pushed farther into him now, and began slowly and gently thrusting, gradually building up speed until she found a rhythm that she could sustain. Harder and deeper she went, trying to kind of pull the strap-on upward slightly at the end of each thrust.

As she looked up, she saw Sandra reach around and unclasp her bra. Biting her lip seductively, she started to massage, and play with her breasts, lightly pinching her nipples.

“AH! Fuck, I’m close baby!”

Nathan needed no more encouragement, and tried his best to find her clit with his tongue.

A few moments later, Caitlyn watched her girlfriend's body convulse in pleasure, a look of pure ecstasy on her face as her whole body shuddered.

“A-ah, fuck, fuck me,” she said as she rode the high.

“Phew, you're really good at that, aren’t you baby?” She said, after coming back down.

She got down from the table and resumed teasing Nathan’s nipples.

Desperately turned on from watching her girlfriend cum so vigorously, Caitlyn flipped a switch on the strap-on, causing it to begin vibrating inside of Nathan.

by this new form of stimulation, he shouted out “AH!” As he felt a pressure start to build deep inside of him. Similar to the one before, this one was much more intense, and quickly washed over his whole body.

Sandra leaned in and kissed him, her tongue fighting for dominance against his, stifling any moans and groans he tried to make. She kept pinching his nipples as his mind went blank from euphoria, being sure to twist and pull quite a bit harder then she had before, to the point of causing him mild pain.

Caitlyn smiled, and satisfactorily said, “good boy”, as she watched Nathan’s entire body convulse in pleasure.

As Nathan came down, he realized that, even though he had just orgasmed, his cock was still rock hard, and that he was still, just as horny as ever. He looked up, a perplexed look on his face.

“As I said slave” Caitlyn said. “Penis stimulation isn’t the only way for a guy to cum. And do you wanna know the best part? Prostate orgasm’s don’t have a cooldown time, so we can make you cum as many times as we want!” She continued in an excited tone.

“Yes baby,” Sandra said. “We’re just getting started! You’re gonna be cumming at least 2 or 3 more times before we’re done with you!”

“It feels good though, doesn’t it? With how hard your dick is, you must be super excited!” Sandra said teasingly.

“Babe,” Sandra said. “Hand me the vibrators and tape.”

Caitlyn did, as she watched Sandra tape one vibrator onto each of Nathan’s erect nipples, now hard enough to cut through glass.

“Some extra stimulation,” she said. “Oh, and we can’t forget about your dick, can we baby?” She said sadistically, as she taped another vibrator to the shaft of his cock and turned it on, being sure to set it to the lowest possible setting, not enough to give him a penis orgasm, but enough to make sure he was constantly on edge.

“You asked us to stimulate your penis baby. So… we are!” Sandra said cruelly, knowing that the constant buzzing was killing him.

“T-that’s not what I meant! Please let me cum!” Nathan said, growing increasingly more frustrated.

“We just did silly!” Sandra replied wickedly.

“N-no! Not like that! Please touc-MFH.” He was once again cut off as Sandra quickly slipped the ball-gag back into his mouth while he wasn’t paying attention.

“That’s better,” she said sweetly, kissing his cheek. “You just sit back and enjoy it baby!” She said, gently rubbing her fingers over his ribs and armpits, not so much to tickle, as much to make him giggle slightly from the light touches.

After about another hour, and 4 more, just as intense dry prostate orgasm’s, Caitlyn spoke up.

“OK, I think we’ve given him enough pleasure. I think it’s time to move onto some pleasure of our own!” She said, shoving the strap-on as far inside him as she could and detaching it from the harness, leaving it vibrating away inside of Nathan.

She walked over to Sandra and enthusiastically kissed her, and massaged her breasts, making sure to give Nathan the best possible view.

Sandra, breaking the kiss asked, “do you want his dick or tongue babe?”

“You have his tongue again love,” she replied as she removed the vibrator from Nathan’s dick.

Relief suddenly flooded Nathan's body from being rid of that god forsaken buzzing of his dick.

Caitlyn climbed onto the table and sat on his chest, removing her bra in the process, making sure to do so as sexily as possible for Nathan’s horny eyes.

As Sandra removed the gag, she shoved her boobs in Nathan’s face, making sure to keep them just out of reach of his tongue.

“Not yet baby,” she said as she climbed onto the table and placed her pussy over his face again, being sure to support herself with her thighs so that her pussy was also out of reach.

Caitlyn began to grind against Nathan’s dick, making sure he could feel her warmth and wetness, resisting the urge to slip it inside her.

Sandra leaned in for a kiss, and Caitlyn started sensually massaging her breasts with 1 hand and reaching down to her clit with the other.

“Are you ready love?” Caitlyn whispered into Sandra’s ear.

“Sure am babe!” She replied.

With that Sandra lowered herself onto his mouth, Nathan immediately began pleasuring her, lapping up her juices with the determination of a wild animal that hadn’t eaten for days.

Caitlyn took him inside of her and immediately felt a surge of pleasure hit her. She had wanted this, needed this, all day long, only just barely managing to control herself, knowing that the waiting would make the final release so much better

. Sandra, smiling sweetly at the sight of her girlfriend’s pleasured face, leaned forward and pinched Caitlyn’s nipples with 1 hand, and reached down to her clit with the other, while she kept riding Nathan’s face.

“Ahhh,” moaned Caitlyn, her head rocking back from the pleasure of having 2 people simultaneously pleasuring her.

Being constantly aroused all day had caused Caitlyn to become pent up beyond belief, she knew she wouldn’t last more than a minute or 2 before she came. About a minute later Caitlyn moaned out in ecstasy, “AH! I’m cumming love! I’m cumming!!”

Sandra just smiled sweetly and said, “cum for me babe,” starting to convulse from pleasure herself.

Caitlyn began somewhat violently shaking, the thought of being here, torturing her slave all day, with the woman she loved, leading to the biggest orgasm she had ever had.

“AH!” She moaned out.

Nathan seeing this all unfold, could feel his own orgasm start to build, Caitlyn riding him had quickly started to push him over the edge.

Suddenly, the biggest wave of pleasure he had ever, and would ever experience erupted from inside him, a wave of pleasure so big and powerful, he would spend his entire life searching for it, desperately trying to recreate it. It seemed to last for hours on end, even though he knew it couldn’t have been longer than 30 seconds or so.

As his eyes rolled back into his skull slightly, he lay there, starting to come down from his high, more satisfied than he ever had been, and would ever be. He couldn't even think as his mind had temporarily turned to mush. He lay there, in pure bliss, for what again seemed like hours, light headed, desperately panting, trying to catch his breath. As an overwhelming sense of calm came over him, he thought to himself as he started to regain the ability to think, “wow, I’m glad I came here.”

As the 2 mistresses also came down, they both got off of him, removing the vibrators that were still ruthlessly attacking his poor nipples, untied him, and began gently cuddling him.

No one said anything, but tears formed in Nathan’s eyes, not sobs like before, but silent tears of satisfaction.

After a few more minutes Caitlyn asked, wiping the tears from Nathan’s eyes, “so, what did you think Nathan?”

Nathan, noticing she had not called him slave, but had used his actual name, stretched his limbs slightly, and softly said, “I-I’m not sure yet.”

“That’s understandable baby,” Sandra said sweetly. “We don’t expect you to say anything yet.”

Caitlyn nodded understandably, stood up, and said, “No, we don’t. Come on, let's get dressed.”

The 2 women helped Nathan shakily stand up, and all three of them walked down the stairs, the 2 women taking care not to let Nathan trip and fall down the staircase.

Caitlyn unlocked the door, flicked the lights off, and they both headed back into the first room Nathan had come into.

Sandra picked up and handed Nathan his clothes that had been abandoned on the floor earlier, and said, “Come on, we all need a shower.”

He followed them into the bathroom, and saw a very large walk in shower, easily big enough to fit 4 people.

He watched as Sandra quickly turned the water on, removing her thigh highs as she waited for the water to get hot.

The 2 women stepped in. Caitlyn looked back and said, “well, aren’t you getting in?”

He did. The hot water pounding against his body, making him feel even more relaxed. He watched as Caitlyn grabbed the bottle of soap and started applying it to Sandra. Sandra did the same for Caitlyn, and then, squirting some into her hand, the 2 women both started to wash Nathan, making sure not to tickle him by mistake. He didn’t resist. He didn’t have the energy to resist, even if he had wanted to.

As they got out of the shower, he followed them into another room in the back, their bedroom he assumed, judging from the queen sized bed.

For a moment, he just stood there, watching. He watched Caitlyn rummage around in their closet for a new set of bra and panties. He watched Sandra bend over and pick up both of their clothes, placing them on the bed. He watched as Caitlyn put on the bright pink bra with red flowers on it that she had pulled out of the closet. He watched as she bent over, slipping the leopard print panties on. He watched as Caitlyn handed Sandra a pair of dark red panties, and he watched as Sandra sat down on the bed and put them on.

After a moment, Sandra noticed him staring. Aren’t you gonna get dressed, pervert?” She teased sweetly, embracing him and kissing his cheek.

Nathan came back to his senses, and began pulling on the clothes he had come in, while the 2 women did the same.

They came out of the bedroom, back into the first room.

Caitlyn and Nathan sat down on the couch, Caitlyn putting her arm around Nathan. “Do you want anything to drink?” Sandra asked.

Nathan, realizing he was incredibly parched from a full day of laughter, said, “A glass of water please.”

Sandra proceeded to grab a glass from a cabinet, fill it with water from the tap, and hand it to Nathan.

He gulped it down with the vigor of a man who had not drank for 2 days, giving a satisfied sigh when he had finished.

“So,” asked Sandra, sitting down on the couch beside him so that Nathan was sandwiched between them, and resting her head between his neck and shoulders. “Did you have fun baby?”

Nathan, still trying to come to terms with what had just happened, just said “I’m not sure.” After a pause, “I didn’t…completely hate it,” he continued.

Caitlyn looked at him and said, “That's understandable. It was a very intense session. The fact you aren’t trying to get out of here as fast as possible is already a little surprising.”

“Most people never come back after their first session,” Sandra said.

“I can understand why,” Nathan replied.

After a brief silence, Sandra asked, “do you think you’ll end up coming back again? We give “special treatment” to our repeat customers.”

Nathan felt a shiver down his spine, imagining what she could possibly mean by that.

“...I don’t think so,'' he said.

With a slightly disappointed look on her face, Caitlyn said, “Yeah, we understand. It’s not for everyone.”

Another silence. “Here though,” Caitlyn said, leaning forward towards a box on the coffee table. “You should still take our card, just in case.”

Nathan took the card and studied it, it was the same logo and graphic that was on the flier, only he noticed the number was different.

“That's our repeat customer number,” Caitlyn explained. “As Sandra said, repeat customers get “special treatment”.”

Nathan shivered again.

“Thanks I guess,” he said, puting the card into his pocket.

After another few minutes of cuddling, they all stood up. The 2 women walked Nathan down the stairs and to the front door. They both hugged and kissed him as he left. “Bye baby,” Sandra said. “Yes, bye Nathan,” said Caitlyn.

With that he left and walked to his car, watching them shut the door behind him.

He found his car and got in, but instead of driving away, he sat there in silence for a while, thinking about what he had just experienced.

As Nathan opened his apartment door and came in, he kicked off his shoes, and grabbed a beer from the fridge. He went to sit down, then remembered he still had their card.

He turned around and walked toward the trashcan to throw it away. “Nope, won’t be doing that again,” he said quietly to himself.

But, somehow, the card never found its way into the trash can. It instead, somehow, miraculously, found its way into his wallet.

END