Mistress Deena Ch 02

Yesterday Mistress Deena and I decided that we would go out on a dinner date, no play sessions and no d/s roles. It was just one day removed from the hockey game incident. We would just have a "normal" date and have great conversation over great food and wine. She insisted that I call her just Deena for the entire night.

We had a great time and got to know each other even better. Mistress Deena is currently 35, got divorced about a year ago and has no kids. She was always interested in the lifestyle, but her ex was never very interested and they just grew apart over time. She went through more details about always being intrigued about being a Domme. Her fetishes are cbt, humiliation, impact play, and bondage.

I am currently 46 and divorced, my kids are grown up and both in college. During dinner, I further explained to Mistress Deena that when I was married, we dabbled in bdsm for about 3-4 years, but my wife didn't want to fully commit to the lifestyle and never truly felt comfortable being a Domme. When my ex wife and I did dabble in bdsm, I was usually in the Dom role, but I always longed for being a sub. We continued to grow apart in our marriage and decided to file for divorce last year.

The conversation with Mistress Deena was wonderful and she looked so beautiful. She was wearing a gorgeous black dress with heels that accentuated all of her curves. I kept on getting lost in her gorgeous hazel eyes that matched her long light brown hair.

After dinner, I walked her to her apartment. As we were standing in front of her steps, she gave me a soft kiss on my lips and said "Thank you for dinner. If you do not have any plans for tomorrow, maybe we can do something?"

A smile came over my face "I would like that!"

"Ok, I will send you a text in the morning." She gave a little raise of her brow, turned and walked up her stairs. My eyes followed her gorgeous body with each step, soaking in every wiggle and movement of her gorgeous legs and body. She walked up and closed the door behind her without ever looking back.

I woke up this morning at around 8:00 and I am currently eating some cereal when my phone vibrates with a new text message. I pull up my phone and I see it is a new text message from Mistress Deena. The message says "Hi Cumslut!"

I take a deep breath and say Fuck to myself. I don't know why but being addressed like that turns me on. I type back "Hi Mistress Deena".

My phone vibrates with a new message "We need to go shopping today."

"What type of shopping Mistress Deena?"

Within 10 seconds of my message a new message appears "Clothes shopping, my pet."

"Ok Mistress Deena". I am wondering if she means clothes for me or for her, but I do not ask.

A new message appears "Be ready in an hour slut. I will meet you outside your apartment. 😘 And don't dress like a slob, I expect you to be dressed nice when you are out in public with me."

I write back "Yes Mistress Deena" and I put down the phone and head into the shower.

An hour later I am in front of my apartment building. I am wearing a button down shirt, nice new dark jeans and black penguin shoes. I look to my right and I see Mistress Deena walking towards me, she is wearing black thigh high boots, designer blue jeans, and a light tan cashmere sweater. She looks sexy and elegant.

I say the only thing that comes to mind "Oh my god Deena, you look so beautiful."

She gives me a stern look "Thank you, but you can only address me as Mistress Deena today."

"Yes Mistress Deena." I quickly respond.

A car pulls up and Mistress Deena says that she requested an Uber car. I open the car door for Mistress Deena and she gets in and I get in on the other side.

The car pulls into traffic and Mistress Deena says casually to me "We are going to Copley Place. Our first stop is going to be at Victoria's Secret. We need to get you some panties to wear."

Her words feel like they echo in the car and I look forward and I see the male Uber drivers eyes meet mine. I feel my face get flushed with heat.

I turn towards Mistress Deena and I see a smirk slowly rise on her face. "I hope shopping for proper attire isn't a problem for you slut? I guess maybe I should have asked first."

I know this is all part of the humiliation fetish that her and I have talked about. I take a deep breath and say "No, it isn't an issue Mistress Deena." My cock is rock hard in my jeans and my heart is racing.

I can see Mistress Deena fighting back the smirk and she turns and looks out the window. Nothing else is said in the car for the next 5 minutes as we pull up in front of the shopping center. The Uber driver lets out a small cackle and says "Have fun shopping" as we step out and close the door.

Mistress Deena and I make our way through the mall and arrive at Victoria's Secret. My breathing is heavier and i can feel precum dripping out of my stiff cock and slowly making its way down my leg. I have never done something like this before.

The store is practically empty, there is just one woman shopping in it and I see three sales women working in the store. I follow Mistress Deena into the store and she is walking slowly and purposefully.

I am looking around nervously while following Mistress Deena. Part of me wants to run out of the store, but another part of me is loving this and I am finding this exciting and exhilarating.

We walk back about four to five racks and Mistress Deena picks up a pair of purple lace panties. "Purple is my favorite color, do you like these?"

I reply with a quick "yes."

"Yes, what?"

I pause and then say "Yes Mistress Deena."

"Good boy."

From behind Mistress Deena, a woman who I would guess is in her late 30s comes over. She has dirty blond hair, brown eyes, is around 5 feet, 10 inches tall and she has a great figure. She looks athletic and you can tell that she keeps herself fit. I look at her tag and it says her name is Michelle and under it says Store Manager. My heart races and I say to myself oh my god, I want to crawl under one of these clothes racks.

Michelle gives a smile, looks at Mistress Deena and says "Can I help you?"

Mistress Deena turns towards Michelle and pauses. Then she turns towards me, looks back at Michelle and says "I'm taking him shopping for the first time. I'm trying to decide if I think these panties are going to look good on him."

The words from Mistress Deena are not like anything I have ever experienced before. The embarrassment is overwhelming and the only thing I can mutter is "fuck!" as my cheeks turn crimson red.

Michelle lets out a small laugh and makes eye contact with me. Then with a smile she looks back at Mistress Deena and says "This is his first time shopping huh?"

"It is. The poor little slut finds this so humiliating. Isn't it adorable."

Michelle lets out a laugh and says "First time shopping is always fun. I have a sub as well. He calls me Lady Michelle."

For the second time within two minutes I let out a single word..."Fuck!", which sparks a laugh from both Michelle and Mistress Deena.

Michelle turns to Mistress Deena, "We definitely should have him try on a few different things, don't you think?

"Yes Definitely" Mistress Deena responds and passes the pair of purple panties to me.

Michelle nods for me to follow her and leads me to the fitting room. As we are walking, I look to my right and the other two sales girls and whispering and giggling while looking at me. I can't believe this is happening to me.

Michelle opens the door to the dressing room, hands me the purple frilly panties and says "Make sure you open the door and show us what it looks like." A smirk forms on her mouth while saying it and she closes the door.

I strip down naked and I put on the purple panties. It's the first time I have ever put on panties. My cock is rock hard and I look at myself in the mirror. My body naturally doesn't have a lot of hair and I have always liked my balls and the base of my cock to be shaved. I also trim very tightly.

I slip on the panties and my hard cock is very visible and the cock head peaks out over the top of the panties. I take a deep breath and I open the door. Both Mistress Deena and Lady Michelle are standing in front of the door with cameras ready and the two young girls that were giggling are standing next to them. Mistress Deena and Lady Michelle both snap pics on their phone.

Lady Michelle purrs.. "mmmm, look at that hard cock in those panties. I think he really likes them Deena.

Mistress Deena smirks back at Lady Michelle and says, "I think I need to get him a cage Michelle. I think he likes it too much."

Lady Michelle nods in agreement and looks back at me. She then points to the girls and says "The girls are in training not only for management here but I am also training them to be a Domme."

Lady Michelle then looks around the store and then faces gives Mistress Deena a kiss on the cheek "Deena, you have my phone number now, let's see if we can all get together tonight. I will pick out panties and lingerie and it will be on the counter waiting for you. Why don't you take him in my office with the girls. You can help me with their training."

Mistress Deena leads me down the hall past the fitting rooms to the managers office and the two girls follow me.

Mistress Deena closes the door behind the girls and says "you like dressing like a little faggot don't you slut?"

I feel my cheeks get red again and I say "yes Mistress Deena."

I look at the girls name tags and their names are Lisa and Kim.

Mistress Deena then says "Bend over the desk!"

I bend over and Mistress Deena pulls down my panties. "Doesn't he have a nice ass for an older cumslut girls?"

The girls make some affirmative grunts and Mistress Deena starts slapping my ass hard with her hand. She does several hard slaps with her right hand on my right cheeks. The noise echoes in the office with each slap.

She then grabs my hair and tells me to lie down on the desk. I lie down and Mistress Deena squats over my face and says "see girls, this is what you do with a slut like this. You feed him." Mistress Deena grinds her pussy on my face and says "He has got such a good fucking tongue." She moans and says "Eat it you fucking whore. Do you know what we are going to do to you slut. After I cum all over your face, the girls are going to help me make sure that you also cum all over your face. So everyone in this mall will know how big of a cumslut you are."

Hearing these words make me lick and suck on Mistress Deena's pussy harder and faster. I hear Mistress Deena moan louder and I can tell that she is getting close to cumming. "Oh fuck, I'm going to fucking squirt all over your face." Mistress Deena lifts up over my face and starts rubbing her pussy hard "open up your fucking dirty mouth wide."

With those words she moans wildly and she begins to squirt all over my face and a bunch of her cum goes into my mouth. She screams "oh fuck!!" As my face gets soaked.

After Mistress Deena cums she moves off the desk and tells Lisa and Kim to pull off my panties and for each to lift a leg and put it straight up.

Mistress Deena then gives a laugh and says "you look so good with my cum on my face, but I don't think it's enough."

She then starts to stroke on my cock and is pointing it at my face. "Don't you think he is going to look like such a dirty cumslut girls, walking around the mall with his own cum on his face."

The girls each let out purrs as precum drips off of my cock and a string of it stretches from my cock to my face.

I plead "No Mistress Deena, please don't make me do this!"

Mistress Deena let's out a little moan "Look at how fucking big your cock head is getting slut! You fucking want this! Your cock doesn't lie!"

I start moaning louder, trying to hold back my cum.

Mistress Deena then uses a more assertive voice "you are going to do this, right in front of these girls. You are going to cum all over your slutty face."

I see the girls holding my legs and can't believe I am doing this.

Mistress Deena is stroking my cock hard and it is pointed right at my face "That's it slut, time to cum...5...4...3...2...1". On the count of one, I lose control and torrents of cum starts shooting all over my face. My eyes are closed and I can feel it hitting my eyes, nose, cheeks and lips. Everyone in the room is letting out moans and several waves of cum hit my face until finally my cock is spent.

Mistress Deena says "Doesn't he look great with his face soaked like that." And both girls give affirmative groans and says "yes".

Mistress Deena says " go back to the fitting room and put your clothes on and then go to the register and pay for your clothes...but that cum better stay on that face, do you understand cumslut?"

"Yes Mistress Deena". and I follow Mistress Deena and the girls out the door and I go into the dressing room. I leave my panties on and slip my clothes over them and make my way to the register.

Lady Michelle is at the counter and she lets out a soft moan and says "Look at you, such a fucking dirty slut with your cum all over your face. You look so good."

"Thank you Lady Michelle" I softly reply.

She rings up the panties, stockings, garters and other items that were selected for me and hands me my bag after the credit card goes through.

Lady Michelle smiles and says "I hope you had a great shopping experience and hope to see you again soon." There is a twinkle in her eye as she completes her sentence.

"Thank you Lady Michelle." I turn to my right to exit and I see Lisa and Kim, they smile and wave.

Mistress Deena is waiting for me outside the store. As I walk to her she says, "ok, I have to get my hair done and I need to do other shopping. You will need to find your way back. And I expect that cum to be on your face until you get home!"

"Yes, Mistress Deena, I will not wipe it off until I get home."

"Such a good boy! I'll reach out to you later." Mistress Deena turns and walks away.

I put on my sunglasses and decide to take the 50 minute walk home. As I'm walking I feel the cum drying on my face. I feel some strange looks but I have no idea if anyone is noticing it and I am thankful for not running into anyone I know. My cock is constantly aching and aroused throughout the walk.

I am within a block of my apartment when I get a text notification on my phone. It is from Mistress Deena and it reads "Hi cumslut, I hope you had a nice walk home. We are going to the sex toy store tonight is Lady Michelle and her sub. Meet me at my apartment at 10."

I read the text and say "fuck" out loud. I seem to be saying that a lot lately and I laugh to myself.