Jessica and Tom 04: New Relations

Jessica moaned gently as she watched Stephanie find her stride her fingers flicking and grinding against her engorged clit.

"How do you recommend I fuck him? Face up or face down?"

"It's up to you Miss Stephanie." Replied Jessica between breathy moans. "For a first time I rather like the idea of seeing his face so perhaps face up on the bench over there so you can pull his legs up easily and get full access to his slutty little sissy hole." She said pointing at a bench in the corner with raised leg pads.

"I like that idea a lot. Candi, fix your lipstick again, I want to enjoy your perfect face as I fuck you, then get on the bench Miss Jessica suggested."

"Of course Miss Stephanie." He said after slipping the drool covered cock from his mouth. He then repeated his previous route the mirror to touch up his lipstick and wipe away as many red smears as he could before tottering to the bench the women had agreed on.

Jessica came over to the bench and helped the novice with the leather straps. Making sure Candi was properly arranged for the easiest access to his ass. She took the opportunity to caress the older lady as she passed and was rewarded with a more intimate touch from her in return. The ladies embraced, both relishing the touch of the others smooth skin and soft lingerie.

Jessica felt the strapon pass between her legs and gently rub against her wet pussy and genuinely wanted what happened next. Stephanie was so horny she wanted to fuck anything and reached for the cock she wore placing the tip at Jessica's wet entrance, then with only a little pressure guided the cock inside her. The couple kissed passionately as the cock slid completely inside Jessica, the two women began to fuck against the bench where poor Candi was strapped. As Stephanie thrusted she delighted with the sensation of the internal dildo pressing on her clit as well as the sensation of the cock slipping deep into her new mentor. The two women moaned as their pleasure build, Jessica knew she had to cum first or Stephanie would miss out on the planned reveal. She ground faster and faster using her own fingers to quicken her orgasm as she rode Stephanie's shaft. Her moans grew to screams as her g spot was pounded and the ribbed veins of the shaft rubbed against her clit. She shivered as her orgasm crashed over her and her cunt spasmed around Stephanie's phallus.

Reluctantly she allowed the cock to slip from her as Stephanie withdrew. "You seem to be quite proficient with a cock for your first time Stephanie but I think it's time for the main event." She kissed Stephanie allowing her caress to linger before the two parted.

"I had no idea how intoxicating a strapon could be. I've never been with another woman let alone fucked her with my very own cock. I'm genuinely giddy." Her flushed grinning face said it all, she was hooked and couldn't wait to fuck her first boy toy.

Jessica slipped a condom over Stephanie's cock then applied a generous amount of lube to both the shaft and Candi's waiting ass. "You should take this slowly for two reasons, one it's only polite to poor Candi and two it's a wonderful thing to watch your dick slip into your first submissive boys ass and seeing their face as he takes every inch of you."

Stephanie clapped with joy as Jessica walked her around and positioned her between Candi's legs. "Now place the tip of you cock on his rosebud, apply just enough pressure to hold it there." Jessica whispered in her ear. "Now gently apply a little more pressure till you feel it start to move in, keep watching his pretty little face as you do, it's just magical, every time."

Stephanie adjusted her hips and applied mores pressure, the tip slowly slid into Candi. Both woman were delighted by the little gasp he let out and the widening of his eyes as the cock slid slowly into his eager ass. "Oh my that is wonderful." She squeaked in excitement.

"It's one of life's true joys to see a manly man totally at your mercy isn't it." Said Jessica as she watched the magical moment for both. Stephanie taking her first ass and Tom fluttering into the world and seeing his HR manager slowly slipping her girl cock deep within him. Not that he could do much about it being he was heavily restrained and highly aroused by all the sensations around him crashing over him.

Stephanie kept the gentle pressure and allowed the cock to slip completely in to him. As it reached the hilt she saw his cock twitch and a small pearl of liquid appear at the tip. "Is he cumming already? That would be a shame!" She exclaimed.

"No don't worry that's just precum, your cock has just nudged his very full prostate. I haven't let him cum for a few days now. Tom would never cum without permission anyway, He simply can't to be fair, I'll explain later."

As Stephanie gently pulled back allowing the lubed cock to slip back out slowly she glanced quizzically at Jessica. "Tom, as in our Tom?"

"Oh yes didn't you recognise him with all his makeup on. Tom's been my plaything for several months now. He's really a very good slave."

"Oh dear this is very inappropriate." She said beginning to panic at the thought of people finding out she had fucked and had her pussy eaten by an employee.

"Don't worry Stephanie, this is totally consensual and out of work hours. Just look at his face, the longing in his eyes as you slip your cock out of him, he wants you to fuck him. As for his little bit of precum...." She scooped the glistening pearl from his tip with her finger, "well sissy's always clean up their own mess, so never miss a drop." She presented it his lips and he licked sensually.

The combination of the dildo in her pussy, the motion of the cock gliding back into Tom's tight ass and the visual impact of seeing him being fed his own fluids caused Stephanie to moan with arousal and quicken her pace. 'In for a penny in for a pound' she thought as her orgasm built. Her thrusts gained rhythm and both giver and taker moaned in delight. She periodically took the dripping precum from Tom's cock and slipped her finger into his mouth.

Her thrusts took a more rapid tempo as her need for release grew to a crescendo. She shook in ecstasy as her orgasm crashed over her squealing in delight as her entire body fizzed. Taking another pearl of precum from his dick she licked it onto her tongue before reaching forward and kissing the restrained sissy below her. Their tongues entwined together as they both enjoyed the salty goo that she passed to him.

"That was truly marvelous, I've never felt so empowered." Said Stephanie as she slowly slid her cock from Toms gaping sissy hole. He moaned in pained arousal as the sensation of emptiness below enveloped him. "He's been so good, I would have though he's have blown his load by now. I feel a bit guilty now as he's the only one left unsatisfied."

"Oh it's not the first time I've left him wanting but you are more than welcome to thank him if you want to allow him release. I do have another idea if you want to go further down the rabbit hole though." Jessica left the idea to hang to see if she would bite.

"Tell me more, I've come this far." She replied, just as Jessica had hoped.

Jessica disappeared behind a screen and returned with what looked like a tissue box and a small beaker, she lay both on the thick strap that held Tom's midriff in place on the bench. "Show me your hand, like this." She held her hand up inviting Stephanie to place hers against it. "Excellent, you'll have no problems." With her other hand she opened the box and handed Stephanie a black rubber glove. "Pop this on and put some lube on your index finger."

"Ooo are we playing doctors and nurses?" Stephanie giggled as she slid her hand into the glove making a show of snapping the edge of it once it was in place. She took the lube and gave her index finger a liberal coating. "I think I see where this is going but didn't we just do this with my rubber cock, which I loved but the way!" Jessica could see she was getting into the swing of things, soaking up new experiences and ideas as quickly as she could. Relishing her control over her prostrate subject.

"You're very close, yes its definitely going in his tight little sissy hole but we're going to try two things in one then go for a slam dunk at the end. First just slip your finger into him with your palm facing up.

Stephanie placed her digit at his rosebud and applied a tiny bit of pressure, his stretched ass provided little resistance this time and her finger slid in easily all the way to her knuckle.

"Good, now feel along the centre of the canal and you'll sense a lump about the size of a walnut, maybe a bit bigger as I've not let him cum for a few days."

Stephanie concentrated as she felt within Tom "Ah I think this is it."

"We'll know in a moment, just apply a little pressure on it, only a little, we don't want to spoil the fun."

Tom groaned in response to her touch. "Yes that's it all right, you see boys have a G-spot the same as we ladies, men call it their prostate, I'm sure you've heard of it."

"Yes but I didn't know it was like an erogenous zone, I thought it was to do with their pee."

"Oh no, its much more than that. You see the sperm they like to ejaculate are all made in their testicles, I'm sure you're aware of that. The prostate provides the semen the little swimmers swim in. If we massage that prostate just right two things will happen, first all their semen will seep from their cock in little drips, just like you saw when you were fucking him earlier. Second the constant stimulation will usually cause the male to experience as close to a female orgasm as possible. You'll see him get more and more agitated as you gently rub him, use a sort of come here motion like this." Jessica demonstrated with her crooked finger.

"Oh I have to see this." Concentrating not to use too much pressure she gently began to rub the lump within his ass. Within moments the first drip began to form at the tip of Tom's cock and he began to fidget against the straps. "Oh my, How does that feel Sissy? Does it feel good?"

Tom gasped gently "ahhh, its, its sooo good Miss Stephanie" he moaned as she continued to finger him slowly.

"Now just keep a steady pace and pressure and lets see how much cum we can milk from him." Said Jessica placing the beaker under his seeping cock and holding it in place. "The sensation is apparently somewhere between a building orgasm and needing to pee. Even the squeamish boys I've tried this with have soon been converted to the joys of prostate massage."

Tom's hips began to move in unison with Stephanie's slow unyielding strokes, each one causing a small pearl of white liquid to form at the tip of his cock. Soon he was moaning and gasping, wriggling against the straps that held him firm just like a woman approaching her orgasm. "This is amazing, I had no idea I could make a man so helpless with just one finger. I'm curious about what the slam dunk is now!"

"All in good time, I don't want to spoil the surprise, just keep stroking his special place and he's putty in your hands.

"You really seem to like this Tom, I can feel your sissy hole clenching and releasing against my finger like a hungry slut" Said Stephanie, enjoying his helplessness, his involuntary squirming and moaning. Tom couldn't reply, by now his senses were overloading, his back arching in pleasure, his mind a fizzing mess. The small blobs of cum had become a steady stream of creamy white liquid drizzling in to the container below his cock.

His moans became louder and louder as he reached his peak, his entire body bucking and shaking against the thick leather that restrained him. "Keep stroking, you can see how powerful this technique is, he's well into his orgasm now, look at him, helpless and unable to function as you hold him in the thrall of pleasure with just one finger gently swinging back and forth.

Relentlessly Stephanie milked his ass, his orgasmic pleasure continued as she relentlessly stroked him, he shook and bucked and ground against her finger to stay in his pleasure zone. The stream of cum soon dwindled and stopped with a healthy measure of creamy liquid now in the cup.

"I think that's all he has to give." Jessica removed the cup and put it to one side and took a gag from the hooks on the wall. The one she had selected was shaped like a pair of oversized open red lips. She placed it into his gasping mouth and tied the leather strap around his head. "You can slip your finger out now and take the glove off and we can move onto the last bit of fun. Come round to the side here with me."

As instructed Stephanie slid her finger from Tom's still clenching ass, slipped the glove off and dropped it in the bin beside the bench then joined Jessica. "Look at how much Cum he had in there." she said picking up the beaker and holding it up to the light.

"Yes it is a good amount and perfect for the next exercise, grab another glove and put it on and make sure it's all good and lubed up all over. Isn't this gag adorable, it gives him a real slutty look and the colour of his lips never smears." Jessica chuckled looking at Tom's ruined face, through his repeated prostate induced orgasms his mascara had run all over his face giving him a look of having given multiple blowjobs. The comedic red lips of the gag added to the whore look she so adored of a used slave.

"Now gently start to rub that nice hard cock, give him a wonderful lubed up hand job, you know where all the sensitive bits are and after that multiple orgasm he's just had he's even more sensitive there. Watch how it twitches as you slip your hand up and down. Feel it throb in your hand as you gently squeeze it." Tom began to moan once again as his tortured gentians were once again over stimulated and his arousal grew to epic levels. "As you rub you can slowly drizzle his cum into his mouth."

"Oh my, you mean we're going to feed him his own cum while we jack him off?"

"Of course, a good sissy always cleans their own mess like I told you." Stephanie took the beaker in her free hand and drizzled a small amount of cum between his gag lips onto his waiting tongue. Every few strokes she drizzled a little more into his waiting mouth where his tongue willingly took it.

"Now in a moment we're going to trigger his ejaculation, the problem is, we already have all his semen so his little swimmers have nothing to swim in so his ball are just going to spasm and throb trying to draw any remaining fluid from his prostate. Its called a dry orgasm and its both incredibly pleasurable and also incredibly uncomfortable. A sort of salty and sweet moment. When we let him cum we'll dump the last remaining cum into his slutty little mouth.

Tom's arousal was not helped by the blow by blow of what was about to happen, he'd experienced it before and knew the sensation was both uncomfortable and mind blowing. Stephanie continued to pump his shaft, making sure she paid particular attention the the most sensitive spots. Tom was moaning deeply and trying to thrust his hips into the slick hand that was tormenting him.

"I think he's ready to blow." Said Stephanie as Tom's back began to arch again.

"I think you're right, Candi gets to cum!" Tom's moans became grunts as his balls throbbed in release, his hips strained against the straps as his orgasm hit him and rippled through his body. Stephanie tipped the remaining cum into his gagged mouth and she delighted as the salty jizz filled his mouth and his tongue twisted around in it like serpent in a white pool. She felt the powerful throbs and contractions through his member as she continued gently stroking up and down amazed that not one drop of spunk came out of the tip.

As his body slowly went from shaking and bucking to a more gentle tremble Jessica said "I think that's enough stimulation for now, his poor little mind is going to be jelly for a while. What a good sissy slut you have been today Tom. Stephanie please could you grab a blanket from the box over there while I release the straps." Slowly she unbuckled the straps, whispering in his ear how proud she was of him and how good he had been for them.

Stephanie returned with a soft fleece blanket and lay it over Tom's twitching body and leant in to kiss him softly. "You have been such a wonderful first submissive for me Tom. I've had a wonderful time exploring your body and mind." She whispered. He smiled but couldn't yet form his words even with the gag now removed.

"Come we'll chat for a bit while Tom recovers" said Jessica inviting Stephanie to join her on the plush leather sofa next to her desk. She grabbed a bottle of wine from her fridge and poured two glasses before sitting next to the no longer virgin Domina "So how did you find that, I'm sorry for springing the Tom surprise on you midway but I doubt you would have played otherwise."

"Yes the Tom thing was a a bit of a shock but.... Wow, all I can say is wow, I had no idea that it could be so much fun and so self affirming to have so much power over another person. Its.... Intoxicating!"

"Isn't it, so where do you see yourself going from here, would you like to explore more?"

"Would I! I want more, I've never been so horny and that was one of the best orgasms I've ever had. There are ideas zipping around my mind, do you think we could play again soon?"

"Of course Stephanie, I'd love to, maybe we'll need to give poor Tom a few days to recover though, the poor mite is literally broken." The pair laughed. "So what do you have in mind?"

"I'd love to dress up a sissy, make him my own, dominate him from being a boy. And I'd love to have him suck off another guy while I watch."

"Hmm, I think we should be able to sort something out like that but at some point you'll need to find your own little submissive. Have you thought about how to do that?"

"I hadn't quite got there yet, my pussy is still quivering from today, I've half a mind to jump back on Tom's poor tortured cock and ride him to another O." Stephanie but her lip at the thought. "I hear what you are saying though, I've never been good with dating though."

"Ah, well if I Can offer some advice and guidance?"

"Of course, I'd love to hear what you have to offer."

"Firstly I think we need to look at your image, give Sarah a call." Jessica handed Stephanie a business card. "She will make you a new woman, perhaps we can join you there one day next week? Candi and I are always up for some pamper time."

"That sounds amazing, I'd love to, let me know when and what I need to bring."

"I'll have my people talk to your people." Jessica quipped. "As for finding a submissive, that's quite easy you just need to know where to look and how to behave. The where is easy, or rather the who, you should avoid the guys that come on to you, they are the alphas. Don't get me wrong, they are huge fun to take home and bang but they are in it for their own enjoyment. The ones you want to look for are the wall flowers. The ones that have made the effort to be out but are obviously awkward around women, they are the beta's."

"Ok I think I get what you mean, sort of the ones you know are the 'nice guys' that you wish would make a move."

"Exactly, now mix that with a sexy new look and a few Domina behaviours and it's a win win, you find a willing submissive and he becomes king of the bar. You are going to rock a sexy cougar look, Sarah will do an amazing job."

"What do you mean 'Domina behaviours'?"

"OK so lets look at how we women generally behave, we tend to reign in our sexuality particularly in the work place. Many of these behaviours are kind of backwards. For example, we wear lipstick all the time, why?

"I've never really thought about it, because it looks pretty?"

"No, although I do agree it's does look pretty. We wear it because it because it attracts men and that happens, sorry to be vulgar here, because it makes our mouths look like an engorged vagina that they might want to fuck." Stephanie pondered the thought. "Now we usually apply our lipstick in the ladies room and then we put ourselves on show. So try this experiment. Take a bold shade, a good red like this one I'm wearing, slip it out in the office or in a bar or restaurant and apply it liberally. Halfway through just look around and see how many men, and some women, are literally transfixed by it. You are literally rubbing a penis around a vagina. Their lizard brains cant help themselves."