“Would you mind if I brought a friend?” She giggled into the phone and I could tell she wasn’t alone. This was a new wrinkle in our relationship though. We’d been seeing each other for a few months now in a fairly light dom/sub relationship. I was about 15 years older than her and she called me “Daddy”, which I enjoyed in a playful way.

“A friend? How experienced is your friend?”

“We’ve played with a dom before together. Just once and he didn’t really know what he was doing but she was very up for it! She’s not really part of ‘the lifestyle’ normally but she’s curious.”

I was fairly experienced, having had maybe a dozen play partners for numerous lengths of time over the last 10 years. I’d been to many BDSM events with them, happily escorted girls on chains around rooms of people in numerous states of undress and/or activity. I was pretty firmly in the “Daddy Dom” arena though. I liked the power play, not so much the pain. I’d played with multiple girls at events but never actually had more than one in my home yet. This would be a new experience.

“She’s willing to do as she’s told? If she’s not into this kind of thing, it could get awkward real fast you know…”

“No she’s definitely into it, just not very experienced. I thought you’d be the perfect person to help introduce her to things. I feel safe with you. I know she will too. And she’ll do as she’s told but might be a little shy. She’s shaking her head ‘Yes’ right now.” She laughed.

“Well since she’s there and understands what’s expected, far be it from me to ruin someone’s fun. She does understand what’s expected right? You explained a proper greeting, the kinds of things we’re into, rules about furniture, all that good stuff?”

“Yes sir. I explained things. She’s really excited!”

“Ok. One thing – I don’t have a relationship with her like I do with you, so she can just use ‘sir’ or whatever else makes her comfortable. She’s not to call me Daddy like you do. And of course no names. Understood?”

“Yes, sir. Thank you Daddy. I can’t wait to see you!”

“Don’t be late, baby. Or you both get punished!” I said it playfully, a smile in my voice. She laughed and I hung up.

I had a couple hours until the girls were due to arrive so I grabbed my notepad. On it was written:

– Greeting

– Inspection

– Punishment?

– Dinner

– Ropework

– Deepthroat lesson

– Cooldown

That was a good 2 or 3 hours plan for the 2 of us. Thinking of the new possibilities with a friend along, I had to make some changes obviously. Everything would take longer and I wasn’t sure how they would interact with each other – had they engaged sexually with each other before? Was this a good friend or a casual friend? How far could I push the relationship to make things interesting for them both? I’d have to test some interpersonal boundaries early so we didn’t ruin the fun in the heat of the action.

I scratched out “Ropework” – that’s fun when you’re close to her and can make it intimate but with 2 of them… I wasn’t experienced enough to keep that exciting I didn’t think. And I had no idea what body type her friend was so it may not be practical at all. I tended to enjoy more acrobatic positions.

Also crossed off “Deepthroat lesson”. I was sure she wouldn’t want an audience for that – it’d be messy. ‘Could use blindfolds though…’, I wondered to myself, picturing her friend blindfolded, hands bound behind her, hearing the choking and gagging and wondering if she was next. ‘And leaves her lower body free… I’ll play it by ear’, I decided.

I penciled in: ” – Main course” in place of the 2 removed entries. I’d have to come up with something based on the energy in the room. Once I found their boundaries, they wouldn’t be hard to push and I could play them off each other. That was my preferred sort of discipline anyway – I wasn’t a sadist or anything.

I wondered about dinner. It would be a simple salad, easy to prepare and serve. I had enough in the fridge for 2 but it’d be fun to make them distribute. Dinner should all the time be small anyway. Inspection could be interesting. My baby knew what was expected but I’m not sure how much she prepped her friend. Just in case, I set out shaving and cleaning supplies in the bathroom.

There was a black yoga mat laid out on my floor with a selection of toys, tools and devices on it. This was at the far end of my living room in my 4th floor apartment in front of a large floor-to-ceiling window, vertical blinds pulled across and about half way closed. You could clearly see out to the wall of windows and balconies across the street and the sidewalks below. From the right angle you would be able to see in. I’d never had any complaints though so if anyone was watching, they were enjoying the show. There was a large, load bearing ring in the ceiling above the toys with a chain running through it. The ends reached down to the floor and had large metal fasteners with a quick release on each.

I looked over the equipment, debating if I wanted to add or remove anything. I did make one substitution. I looked forward to a surplus of fingers, tongues and other manipulative body parts that night so I removed a couple of vibrators to the box in the closet with my spare supplies. In their place, I laid out a large, flesh-colored strap-on dildo, black straps attached. I had to put it on myself over my jeans to be sure everything was in place and find out exactly how it went on quickly and was adjusted and secured. When I felt comfortable with its operation, it laid neatly between a couple other dildos, dwarfing them in size. It had been a while since I’d used it but I knew it was an intimidating thing to see on a pair of curvaceous hips. I added a spare ball gag and blindfold as well as a second leather collar. I did not have multiple sets of wrist and ankle cuffs but didn’t use them much honestly – they were mostly in the “fun to look at” category like the leather whip or the hobby knife. Scary if you didn’t know that I’d never used them and never planned to.

I showered, shaved, brushed and dressed. Simple black slacks and a button-up, no undershirt. Short boxer briefs that looked athletic and rode low on the hips. I was in reasonably good shape but didn’t have a 6-pack or anything – 6 feet tall and about 210, naturally stocky with a little muscle. Nice arms and hands I was told. I checked the apartment once more from the bedroom to the bathroom, kitchen and living room. All clean and ready for business. Checked the hallway outside for anything unexpected and found nothing. The night was ready to start.

My phone rang at 6:57 – the gate on the ground floor that let you into the building. I entered the code to unlock it but said nothing over the speaker. Good to leave the friend in anticipation. A couple minutes later there was a light knock on the door. I opened it, and we were 3.

The girls stepped in and I had my first look at our new guest. They were both dressed simply but stylish enough to go out if that’s where the night took us. My play partner was a blond with long wavy hair who I kissed on the cheek after closing the door behind them. She was younger and not thin but still very sexy. I could clearly see her large breasts under the sheer top and her skirt rode high over bare legs and heels. She might be able to hide the strap-on under her skirt if I wanted to take them out. Memories appeared in my head, girls in the back seat moaning while I drove through town. I could feel the tip of my cock starting to stir against my slacks.

“How are you, baby?” I said, holding her hands out to take her in. She looked up at me, all smiles.

“Better now, Daddy!” She shook her shoulders, tits swaying under her blouse, a weakness of mine. Her friend smiled too.

“Good. And you brought a friend!” I looked the other girl in the eye and she met my gaze. A bit larger than my girl, with shoulder-length hair dyed red and dressed more casually in some dark cropped pants and a tight shirt with a collar. Also big breasted, she was wider in the hips but not overly large. I kissed her cheek as well and she accepted my hand on her hip gracefully. I looked at the friend but spoke to my girl, “Is she ready for a little fun tonight?”

“She is!” My baby exclaimed.

“You girls have been hanging out today?” They both had bags I took from them as we talked and placed them in the coat closet. A change of clothes, some sleepwear most likely, toiletries. No jackets.

“We have – I haven’t seen her in a while so we had some lunch and caught up. When I told her I had a play date she got very interested…” she said with a sidelong glance at her friend.

“You said you played together before, right? How was that?” I asked, starting to feel out their relationship.

“We had fun. It was about a year ago and we didn’t know the guy too well so it was a little tough to relax. No sex or anything, just some light fun and some roleplay. I don’t think he was too experienced.”

“Good to know. Luckily we’re a lot more comfortable with each other, right?”

“Absolutely.” she confirmed. I noticed she had reached out and taken her friend’s hand to reassure her. I was remaining aloof for the moment and focused my attention on my girl.

“So you explained a few things to her?”

“Yes, sir. I told her about a proper greeting that you always get and that we do inspection. She knows we aren’t allowed on the furniture unless ordered and there are no names used.”

“Good,” I said, stepping a little closer to her and taking her head in my hand to pull her in toward me. “She’s comfortable with her body and OK being naked in front of you?”

She took a step closer following my lead, her breasts touching my sternum as we came face to face. “Yes, sir. She’s just not as experienced as me and might be a little shy.” Her eyes darted to her friend and back to mine. I gave her a nice big kiss as her friend watched and our tongues met. I kept her there a little longer than ordinary. She still held her friend’s hand but the other one came up to my back as I pinched her nipple lightly through the fabric of her top.

I stiffened my grip on her neck a little and took a more serious tone with her. “So I am wondering one thing.” Her eyebrows raised as she looked me in the eye. “If you explained the greeting, then you also explained that I expect a good girl to do what’s required without me having to ask, right? That I don’t like having to micro-manage?”

Her eyes changed from playful to slightly more pleading as she said “I’m sorry, Daddy.”

Raising my voice a little I said “I didn’t ask how you feel baby. I asked if you explained a proper greeting.”

“I did, sir.”

“Then I have one question. Why is my cock not in your friend’s mouth right now?”

That took a second for them both to register. The friend looked at me, then her, not sure if she need to do something. I held up a finger in front of the friend’s face to stop her as I took my girl’s chin in hand. “Why is that, baby?”

“I’m sorry, Daddy.” she repeated. “I wasn’t sure… I thought…”

“If you had explained, she would know that I expect her to greet me as soon as she enters my home, wouldn’t she? Just like I expect from you? Right?”

“Yes, sir.” she said. She went to lower herself to her knees but I held her chin firmly, forcing her to stand instead.

“Then I ask again,” I said, pointing to myself and then shaking a finger at the friend, “why is my cock not in her mouth right now, baby? Why?”

She stammered a little. “Because I didn’t explain… I didn’t explain fully, sir. It’s my fault, I’m so sorry. Can I greet you now, Daddy? Please? I can show her how to do it right the first time…”

I noted she was comfortable with sex acts in front of her friend. That was a good begin. I assumed the friend felt the same, although obviously we had never met. Could take a little time to get her to relax.

“What happens when you make a mistake, sweetie?”

She was silent for a few seconds before saying “I’m punished, Daddy.”

The energy had changed in the room now. I had their attention, all eyes on me, ready to please. It was time to test them and be sure the friend was ready for this.

“That’s right, baby. When were you last punished?”

“When I was late last time.”

“I put you over that chair right there didn’t I sweetie?” She nodded and glanced at her friend again. “Dropped your pants to your ankles and took off my belt. You got a swat for each minute right?”

“12, Daddy.” Her lids were heavy as she started to feel a familiar stirring as well. “I was a little sore the next day.”

“I remember, baby. Not today though. Today we have a new way to teach you a lesson. You brought it with you.” I gave the friend a look square in her eyes. I had to shock them both and let them know I’d be playing them against each other. That it was every girl for herself tonight.

“Your punishment will be clean up duty.” I let that hang in the air, unexplained for the moment.

“Clean up?” she asked. She looked around, thinking I might mean maid service. Time to put my cards on the table.

“When I fuck your friend tonight, it’ll be your job to clean us up afterward, understood baby?” I held her face tight so she couldn’t look at her friend and kept my eyes locked with hers. I took her face in both my hands. “You’ll enjoy that, won’t you?”

“Yes… sir.” she answered slowly, clearly coming to a reluctant decision.

“Say it, baby. How will you pay for your mistake?”

“After you fuck Sh…” she stopped herself, “After you fuck my friend, I’ll suck you clean and then lick her pussy clean too, Daddy.”

“Good girl. And don’t make me ask you – what do I like, baby?”

“You like enthusiasm.” She smiled a little, feeling more giddy now.

“That’s right. I like a girl that knows what to do and does it happily, don’t I?”

“Yes, sir.”

And then I finally heard her friend’s first words to me and could feel her energy too, flowing freely now between the 3 of us. The mood was shifting again to something decidedly more pleasurable. “May I please greet you properly now, sir?”