Trained by Aunt and Mom Pt. 02

I smile at Alex "Honey, porn tells you only a small part of the experience. As the appointed secondary teacher, I approve of this curriculum."

"Maybe you should be the head teacher, you were always better at discipline than I was." Meredith adds.

In a more serious tone she asks, "Alex, are you okay with this? BDSM can be a bit of learned taste and not everyone likes it. At least you will see the place where the real work happens."

"Based on your browser history you are at least somewhat interested. But seeing is not the same as experiencing." I clarify. "Remember Positive Consent. If you don't want to do this, then we won't, but otherwise you will follow our instructions and tell if something goes too far. We will take it easy on you."

"In the beginning at least." Mer adds wickedly.

After we get our stunned fish in Meredith's car, we drive towards the small industrial sector on the outskirts of the town. It has been a while since I've been here and the drive brings back so many memories.

We park in front of a non-descript building that houses a glazing company and a car painting shop. In between these there is a door that Meredith opens. We walk in and arrive at a small waiting room with a couch and a small work desk at the end. We could be at the dentist's office for all the decoration there is. There is a laptop on the desk, but the place is almost bare. Obviously not somewhere you plan to spend a lot of time.

"There's the toilet if you need it." I say pointing. "There is the door to the break room that works as our changing room as well. There is the customer dressing room door."

We exchange a glance with Meredith, and I say sternly to Alex. "You will go to the dressing room, remove all of your clothes and wait there for instructions. Is that clear?" I see him hesitating "Is that clear?" I repeat. Mer disappears into the break room.

Alex blinks and after a moment turns and head toward the changing room. I follow Meredith and soon we are changing.

"I don't know what I'm going to wear." she laments to me. "It's Alex. Help me."

"I say we give him the full experience. As we don't yet know what he's into, let's just use the generic setup." I say stripping.

I decide on black leather corset that leaves my tits open and has suspenders for my stockings. I deliberate whether to put any kind of panties on, but they do not really fit with the corset, so I decide to let myself to be on full display. I probably should have shaved my pussy but there is no time and Alex seemed to like it enough yesterday. I top the look with 4-inch stilettos.

Mer is putting on almost the same look that she had before coming here, except this time the dress is black latex that sits on her as painted. She dons a pair of high-heeled knee-high latex boots and seems to be ready. Everything else is waiting in the dungeon.

We make our way there and open the dressing room door. "Come here." I instruct Alex with my domina-voice which - to be honest - isn't that different from the one I typically use to correct him.

He walks into the dungeon and gapes openly. Not just at us but the place as well. It is rather well-equipped dungeon even if I say so myself. It is largish room that is painted clean white and has a big mirror on one wall. On one hand there is a comfortable looking couch and on the other, there is the cross. Amongst other things. Cupboards for the tools of the trade and separated area on the floor with drain in it. So many hours spent here come back to me.

I do not let him to inspect his surroundings long. "On your knees before us. Now. You will only talk when you are answering questions."

To his credit he obeys relatively rapidly, and we proceed. "As we have not done the prework with you as we would be with a normal customer, we need to take things as they come." Mer informs him.

"To begin with, we give you a safe word. It is 'Strawberry'. You use it anytime that you feel overwhelmed or there is something that you do not wish to do. After that we either discuss things or just let off what is happening. Most important thing is that you feel safe here with us."

"If you are unable to say the safe word, tap three times. " She finishes. "Is this clear, boy?"

"Yes" he answers. Oops. "Yes, Mistress" I remind him. "Yes, Mistress" he repeats obediently.

"Good. If you fail any tasks, that you are given, you will be punished. Being disrespectful is also punishable." I clarify.

I consider not letting him to look at us, but I want to feel his eyes on me, so I give up on that.

We walk in slow circles around him looking down. I see the unbridled lust and excitement and ... well... somewhere else. "Mer, would you say that he has a hard on?"

"Indeed, he has. Pity that we are not going to be doing much with it." she answers enjoying the flash of desperation in Alex's eyes. "Let us begin. Boy, do you enjoy pain? In any amount?"

"I ... maybe...? Kinda yes?" he stammers out.

"Answer with 'Yes, Mistress' or 'No, Mistress'. This is your final warning." I say to him in sharp tone.

After a moment of consideration, he answers "Yes, Mistress."

"Very good." A plan is starting to form. The routine comes back to me surprisingly easily.

"Follow me. On your knees." I move towards the other end of the floor where there are rings attached to the floor. The room has heated floor, we are not barbarians after all.

Mer gets the drift and gets the cuffs from the cupboard. Quickly and efficiently, we tie him spread-eagle on the floor. "Comfortable down there?" Mer queries.

"Yes, Mistress."

"We need some information from you about your leanings, but we need something to make sure we have your attention." I say walking to the cupboard. I pick up adjustable nipple clamps and show them to Alex.

He looks like he is going to protest but I give him a stern look and lift my eyebrow and he calms right down. I attach the clamps and adjust them based on his reactions. When he looks like he is going to start struggling, I give the clamps quarter of a turn back and get up.

"Now that we have your attention, we will get right down to business."

We go through the prework list of do's and don'ts with him. He behaves well, earning only some punishment that Mer happily keeps the track of. We allow him to elaborate on some of those and not just stay with binary answers.

I'm not as surprised about the things he is ok with as I thought I would be. I had seen his browsing history and as a professional looked at it with that in mind. Not that I ever would have thought to be in this situation.

We leave him for a moment and decide on the session. We'll keep it simple and short as we want to spend some quality time with him after.

"Well, boy. While Mistress Meredith gets things ready, we have a good chance for you to please me. Do a good job and we might be lenient on your punishment. Or not." I say standing right above his head. He has unobstructed view of my pussy and I'm surprised how much that affects me. I feel the wetness engulf my hole and by impulse I take a wider stance and spread my pussy lips with my fingers. Not just a little, I spread myself so that everything is brazenly on display. Seeing him unabashedly looking up my spread wet cunt is so arousing that I go weak on the knees.

With some strength I gather myself and ask, "Are you enjoying the view of my pussy, boy?" He affirms as the good boy that he is.

I just simply sit on his face. "Now, make yourself useful." The sounds coming from down below where he is working on my soaking pussy drive me almost out of my mind. Not saying anything about how it feels. As my body inevitably starts to give signs of an impending orgasm, I see Mer leaning on the cross and enjoying the show.

It's not that she hasn't seen me in such situations before. We had done some threesomes with our customers and while I wasn't exhibitionist by nature, I really had very few things left that bothered me.

Thus far I had mostly hovered on him but now I lowered myself that so that he was totally immersed. That was one kink on his list checked, I thought absently as I concentrated on the feelings in my sensitive clit. Few seconds more and I shuddered and came. Knowing my role, I did not make a show of it but stood up and curtly said "That will do." while looking at my sons messed up face. There was a happy look to be found under my juices.

"Unfortunately, it is not enough to save you from the punishment. You've been disrespectful and that is something we will not tolerate." Mer says coming to us.

We unclip the cuffs from the rings and march him to the cross and attach him there face down.

I gently slide my hand on the skin of his back. "Such smooth skin. It is almost a shame to ruin it."

Hearing this he shivers on the cross and as he looks like he is getting his courage to stop us, I whisper to his ear. "Trust us. Safe, remember?"

Meanwhile my trusty colleague has brought us selection of different implements to use on him.

"Will you do the honors?" I ask her mostly for the show as she already stands there with a stripped leather whip in her hand. "What is to be his punishment?"

"For each infringement and disrespectful act, five lashes. So ... 30 lashes." I raise my eyebrow at her hearing this, but she continues "If we find that you are not taking your punishment properly, we will need to punish you more. Please, count it out, will you?"

I move so I can see his face and be able to gauge his reaction and start counting. "One.."

Meredith is a professional and hits him in the upper back with a force that while not truly painful, stings a bit. It's more the surprise and sound that makes him open his eyes wide and twitch on the hit. I see her looking at me, but I give no indication to change things. "Two."

The whip slaps mercilessly on his bare skin. Another twitch. This time I do not count, and Mer hits him again as he is not expecting it. His eyes start to show fear as he understands that he is not in control of the situation and that we can do with him as we please.

We go through the lashes quickly and Mer works over his whole back and ass. His skin is tinged deliciously red as I walk behind him, sliding my fingers lightly over his back. It seems that he is not hurting really, we went very light on him compared to some other, more dedicated masochists.

"What do we say now?" I ask leaning in and whispering directly into his ear. He looks panicked as he does not know what is expected of him. He will learn.

"It seems that the boy is not properly thankful for his lesson. I think we need to up the ante." I tell my co-domina. As I know that waiting increases the excitement I slowly go to the cupboard and browse it without any hurry.

I select a sleek paddle and get back.

Meanwhile my lovely sister is standing by Alex and feeling his cock.

"Suzy, I think he likes this." She comments. "He is hard as a rock over here."

"Well, then he will enjoy this even more. Five hits with the paddle until he is properly thankful."

I position myself behind him and feel up his butt. Mmm... nice and tight. Expecting a hit, he jumps from the touch.

Taking a step back I give his behind a measuring look and smack his ass cheek with the paddle using way more force than Mer used previously.

Alex let's out a strangled cry. "One." I tell him. Without letting him get used to the idea, I hit him on the other cheek as hard as previously. Another cry. "Two." As he seems to be taking it so well. I give him the rest in rapid succession. After that he has noticeable paddle marks on his ass.

I again go and enquire him. "What do we say now?"

This time he gets it and fervently breaths out "Thank you... thank you Mistress."

"What a well-behaved boy." Meredith remarks while Alex shudders slightly on the cross.

We let him down and ask if he wants some water. While he is tenderly sitting down and sipping his water, I ask him. "Alex, you have now given and taken. We can stop here but if you want, we can continue. This is purely your decision. We have your list now and if you want to do this again some other time, we can. "

"As long as I don't have a customer." Mer adds.

He thinks for a bit and says "I've liked it so far. I would like to continue for a bit... Mistress."

"We have raised a polite boy, it seems. I think he deserves a reward." Mer says delightedly.

After a small breather it's on again.

This time we guide him towards a bondage horse, where he lies down on his stomach but practically in kneeling position. We fix him in place and as he settles down Meredith asks him "What do you expect to happen next, boy? You may answer the question."

He tests his bonds, but he is tied down properly and there is not really any slack in the ties. "I... I don't know, Mistress."

"You must at least have some guess...?" I prompt.

He ceases his struggle and answers "Whatever happens next is what you decide will happen next, Mistress."

Mer and I look at each other. How we haven't noticed this submissive side of him earlier is anyone's guess.

She gets in front of Alex and pointedly puts on black latex gloves snapping them.

"Well. Let us just say that you are not going to be seeing much of what is going to happen." she says walking behind him.

We just spend a moment of enjoying the view of his backside that is so open before us.

"Just relax and remember that you have a safe word." I instruct my now shivering son.

We have spared no expense and this horse is the kind where there is a hole in the seat for the cock of the submissive. We have full availability to any part of him that we wish. I can't but note that based on his hardness, the shivering is more anticipation than fear. But you never know.

I don my gloves as well. Without saying anything Mer takes the lube, spreads his ass and dribbles the lube onto Alex's crack and smears it gently around not forgetting his dangling balls.

As the cold lube hits his skin, he takes in a short sharp breath. She continues to add lube and starts to focus the massage on to his puckered star. We are in no hurry, and she gently massages his balls, perineum and circles his hole until he relaxes again.

Then slowly as she's circling, he lets her fingertip slightly dip into the tight hole. And out again. Every time going deeper until her finger is completely in. The only noticeable effect of this is that his breathing has become significantly faster.

Looking at her working is amazing. She is completely focused and is gentle and determined at the same time. Alex is in really good hands, I think.

For a moment she just lets her finger just to be inside him. Then she does something and Alex gasps.

"It seems that you still know where the prostate is." I comment to her casually.

She pulls her finger out, adds some lube and back in she goes. This time based on Alex's reactions she has started properly massaging the sensitive gland inside him.

I go beside them and kneel to watch as his cock starts leaking precum. He has started making eager noises under the insistent ministrations of my sister.

Then she pulls her finger out and says to me "It's almost as if he's enjoying it. I wonder if something bigger would fit in there as well." We already have something ready for this.

It is a longish butt plug with small nose but relatively steeply increasing diameter.

While I lube up the plug. Mer goes and kneels in front of Alex. She grabs his head and kisses him. "Alex, tell me when it starts to properly hurt."

I kneel behind him and start inserting the plug. The beginning is a bit difficult but as he relaxes more, it gets easier. Every time it starts hurting, I stop, pull a little back, and try again until we reach the hard limit.

Alex is sweating and his hard cock is leaking all over. Mer takes his face gently in her hands and tells him seriously "Alex my dear nephew, my good little boy. We are going to do something so dirty and depraved that I've never seen the like. And that is saying something in this line of work. " She kisses him again.

"Your mother is going to fuck you in the ass."

Meanwhile I have put on a strap-on noticing to my delight that it still fits. I select a dildo that is slightly smaller than the limit we found and about eight inches long.

The enormity of what we are planning is starting to hit Alex hard. For me and I guess for Mer this is somewhat easier because this is something that we have done often. Together and separately. But still the breaking of one of the last taboos feels quite enormous.

I step behind him and gently probe his anus adding lube at the same time. He seems to be relaxed enough and I have Mer monitoring the situation, so I slowly press the head of the dildo just tiniest amount in his ass and stop. Everything seems to be ok, so I continue pushing. At half-way point we need to stop for a moment but soon enough my hips touch his ass.

Then I ask "Alex, love. What would you want me to do?" I see Mer grinning as Alex huffs and groans. "Feels good doesn't it. But what do you want to happen next?"

I hear the tiniest "fuck me." but I ask again "Tell me what you want me to do." Same tiny voice answers. Mer grips his face tightly and says, "Tell it loud and proper, boy."

"MOM. FUCK ME ALREADY." he yells, his face red.

"There you go. Good boy." I answer and pull out, pushing it right back in. I hear an answering groan and start to properly fuck him as he asked. Slower at first, but soon wet noises, slapping of skin on skin and his moans fill the room.

As I give him it good with a steady rhythm trying to aim for his prostate, Mer moves besides us and puts her hand below the horse.

"What do we have here!" she exclaims joyfully and based on the sounds Alex starts making it is not hard to imagine that Mer is stroking his cock.

After this has continued for a few minutes and his utterances and moans start to reach crescendo, I tell him in my no-nonsense voice. "Alex. Soon I'm going to tell you to come and when I tell you, you are going to come like you've never have before."

I estimate the proper moment and order "Alex, come! Come for mommy!"

Almost immediately he lets out a huge wordless bellow and his body starts to convulse in the thrall of his orgasm. Mer skillfully milks him out while I slow down a pull out after a moment.

As the end of the dildo pops out of him, he goes completely slack. Only the rapid movement of his chest as he pants tells us he's alive.

We leave him be for a moment and clean up the mess. Then we untie him and help him to get up. With his legs shaking, we guide him to the sofa where we have set a towel for him to sit on. I wordlessly hand him another moist towel so he can clean himself.

"So how was it, darling?" I ask him with a suppressed smile. "You don't have to call me Mistress anymore."

He tries to start saying something. Stops and tries again. No words leave his mouth.

"That good, huh?" Meredith smirks. "We really should have charged him. He would pay anything. But we'll let this be a freebie." she thinks for a moment "Or he could pay us with his body. Either way works."

"Mer, that is a bit too much. Look at him. Do you think he is ready for your jokes?" I admonish.

Then we sit on either side of him and just hug him gently. As he slowly comes down and is not shaking anymore, I say "Let's get you home and to shower so we can show you what proper aftercare means."

Next hour goes quickly as we all change, close the place up and drive to my house. Alex is still not saying much but looks quite thoughtful and we let him process the experience in peace.

At this point it is past dinnertime, so I quickly order us some pizzas and we go into the living room. We naturally gravitate to our usual places, me and Alex on the couch and Meredith opposite in the easy chair. For a moment it is almost as if he never had moved out.