Christmas Business in New York

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Tem 24, 2022 // By:analsex // No Comment

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Carla has visited my NYC office on many occasions. She is a product manager for one of the lines of formal female dress shoes my stores and consignment partners carry. Once she had a late flight and had to check out by noon from her hotel. I let her put her luggage in my storeroom and offered to make her dinner at my week-day apartment just around the corner. She felt safe with that. I’m twelve years older; we have a working relationship to protect; we had little time before her flight and I had no plans to take advantage of her.

Before dinner she browsed through my very nice but not ritzy penthouse; nothing close to the down town multi-million dollar ones. She was a little late making it to the table after I had everything ready. Her face was flushed and her eyes sparkled. She did bow her head trying to hide her eyes and embarrassment.

“What’s wrong Carla?”

“I looked in your bedroom.”

“I should have locked that door.” I poured her chardonnay, “You are a beautiful woman, well out of your virginal teens, what embarrassed you?”

“Your art.”

“I’m a dominant, playful, oral male who enjoys women and fetish art – no real pain, just D/s play.”

We had a wonderful meal filled with pleasant conversation. I learned a lot about her small town upbringing with her homemaker mother, her proper finishing school education and rather militant feminist activities during college. I mostly listened. My few words kept her going and her words poured out, telling me a lot about herself. We left the dirty dishes on the table after desert. We had no extra time. We had to get her to the airport. During the drive she divulged a couple more things and learned one that made her gasp quietly.

“You really practice the Dominance and submission, male over female things in your life?”

“D/s works both ways. I don’t need or want a slave, but the women I chose want to feel power, be protected and serve in return.”

“I don’t believe in that role playing stuff. It’s silly to me. I don’t need that.”

“We had whipped cream in our dessert. If your favorite date, tied a napkin over your eyes, stood behind you and put a spoon full of whipped cream on the front of your neck so it would melt, run down into your dress and across your breasts, would you stop him? Or would you let him kiss you deeply, hold your hands behind you, trapped between his thighs so you could feel his cock grow from wanting you. Could you enjoy feeling him lick and kiss your body, while he sucked the cream from your breasts and inhaled your pheromones. Would you feel power over him knowing your wonderful body was stealing his intelligence and making him insane wanting more from you?”

We drove up to the unloading area for her airline and I helped her out of the car and unload her baggage. I tipped the porter and then grasped the collar of her coat, “This is very unprofessional.” I pulled her to me, she exhaled and I sucked in her breath. My tongue licked at her lips and I filled her lungs with my breath. Her eyes were dreamy. I left her with only one thought.

“Thank you for visiting with me tonight and then sharing some verbal play. I will go to sleep tonight with the Dominant fantasy you allowed me.”


The Christmas season was wonderfully profitable. I received a bonus from Carla’s company. It wasn’t much but I wanted to spend it on her. She had resisted twice over the telephone but nature made our decision. I had not seen her for three months. In late January, she arrived in New York for only one night but that night it snowed. I slept in at the townhouse. She slept in her hotel. The next night was Friday the airport was still horribly backed up. Her flight had been canceled. Almost everything else was open. I couldn’t get to my home in the suburbs according to my neighbors. We met half way at a famous restaurant where I frequently dinned. It was slow enough that my favorite, blond cougar waitress had time to cater to us. We had teased often but she said I was too old for her. She is Carla’s age but far more verbally playful.

Carla and I knew we had nothing to do but spend the evening dinning, so we took our time. She was dressed in a black form fitting dress with a plain black nit band around her neck. For over an hour we delayed ordering and got into our second bottle of champagne. She turned the conversation quickly and shocked me, “You surprised me, when we had dinner at your house.”

“How so, pretty lady?”

“You twisted things and I almost believed in your D/s fantasy.”

I felt her disappointment and challenge. I took all the keys off my inch-and-a-half diameter gold plated key ring, complete with four links of matching chain. She looked puzzled. “The restaurant is only half full tonight. Will you play and experiment with me here?”

She did not answer but her eyes were full of questions. Our waitress arrived with some stuffed mushroom appetizers just as I asked Carla if she thought such a small thing would make a difference to how she felt wearing her wardrobe tonight?

Indignantly casino siteleri Carla answered, “No, it might look silly but a gold ring would not be noticed by anyone.”

I scooted closer. The waitress had to move. I put the ring through the material on the front of the black stretchy band around Carla’s throat. It hung freely and visibly down from the middle of her neck. My waitress looked at her smiled and said, “I’ll give you two a little more time to decide on what you want…(she paused)…to order, that is.”

Several of the female restaurant patrons pointed and whispered to their partners. The light was starting to come on in Carla’s rebellious mind but she still was puzzled.

“You are announcing proudly to the world that you are mine tonight. Whatever I want, you will willingly do to please me. You are proud to be submissive and will follow my lead to give us both pleasure.”

Our waitress arrived again; she whispered so Carla could hear, “God that’s hot.” She looked at me and continued, “We never finished our last conversation.”

From my inside coat pocket I pulled out an ad for the best kangaroo cat-of-nine tails made by a prize winning Australian whip maker. As I unfolded it, I talked to our pretty waitress, “Next month is my birthday. See what present I ordered for myself? Remember I told you the last one was too hard and harsh. Even when used lightly, it would have left welts instead of erotic stinging stripes for me to kiss and leave you dripping down your thighs.”

Our waitress put her pad down, lowered her eyes and held on to the edge of the table imagining the sting while still viewing the beautiful red whip. Her breathing was irregular but she gathered herself together enough to ask, “When you get it, will you bring it in so I can feel its leather braids?”

I asked her, “Do you want to touch one and smell the leather or do you want to feel the tassels and imagine them lash across your naked ass?”

She almost came. Months and months of teasing conditioning with a woman, who sometime in her life had willingly felt an expert’s hand with a whip, had paid off. She was frozen.

“Carla, show me you have the guts to try and understand power play. Reach under her skirt and see if her pussy is wet.”

Carla’s eyes were bulging. Her body trembled at my challenge She needed to prove she was as sexually adventurous as me. Our space was secluded. Her right hand reached across her body and slipped under our waitress’s skirt. I could see the waitress uniform move as Carla’s fingers rubbed and thrust and pinched. Our waitress broke all the rules and sat down in the empty chair separating Carla and me. I would not let up, I whispered, “When you come back with our salads, do not have panties on. Carla will push two fingers into you and will feed me your wetness. I’ve always wanted to taste you.” Her mind was spinning, her eyes did not focus and she stumbled twice making it back through the dining room to get to the kitchen.

Carla was statue still.

“Was she wet?”


“Go ahead, taste her.”

With only a moment’s hesitation, Carla licked her fingertips.

“Your decorative neck band is now seen as a sub’s collar by everyone, male and female. You are allowing me to direct you and your body is responding to its own submissive advertisement. Do you feel its demand to please and be pleased?”

Our salad arrived and Carla almost put our waitress into a screaming orgasm. The black and white French maid’s outfit seemed out of place sitting with us while Carla’s wild eyes and nervous shaking fingers fed me our server’s slippery, stringy, dripping wetness. Carla went back for seconds because I finished the first course. I saw Carla’s hand tremble when her fingers entered our waitress and her thumb began to molest another woman’s clit. I challenged our waitress, “Bet you didn’t get to her at all. I bet she is as dry as the desert. Prove me wrong.”

Our waitress was worked up, got strength from my words, stood, put her back to the sparse crowd and literally crammed her right hand between Carla’s thighs and drove two fingers past her panties’ legs. Carla set upright and rigid. I waited. Her mouth opened and I pushed a piece of warm French bread into her mouth for her to bite and scream into. A couple of minutes later, Carla’s eyes rolled back and her body shook for a few seconds before it visibly relaxed. Our waitress touched her wet slippery fingers to my lips. I licked. She left. In another minute, Carla whispered, “I wet my skirt and the chair.”

I had to admit to her, “You should have been sitting on my mouth and I would have swallowed everything, keeping you dry and not embarrassed.”

After the entre, Carla made a trip to the ladies’ room to “freshen up.” I made a mad dash three doors down to get her a present. I was back in place by the time she returned; coffee and cheese cake were served; she had dried most of her wetness but I could still smell her because I wanted to.

A super big güvenilir casino tip was in order for our waitress. I also told her when my cat and I would be back to see her. When I walked Carla to her hotel and left her at the door, I gave her, her present. “I want you to do me a special favor. Take your present and when you are finished, immediately call me, regardless of the time and tell me “good night” so I can hear your satisfaction.”

She looked confused but she would understand when she un-wrapped the expensive vibrator that would help her relax and then her breathy words would help me sleep.


Carla called me from the airport just before her boarding call, “That was wild and out of control at the restaurant last night. And later the phone sex was hot when you made yourself cum on your stomach for me. You won’t tell anyone will you?”

“I hoped you know me better than that. I will never tell anyone. Remember, you know some of my secrets too. You were every man’s fantasy last night. You still have me crazy wanting you. I’m so happy you felt safe enough with me to let yourself experience a little D/s play. I feel closer to you this morning. Remember me once in a while when you are being pursued by all the handsome young studs that drool behind you at all your worldly stops.”

There was a pause, she started to say something but quickly interjected, “Oops, there’s my boarding call, I have to run. Will call you in a few days and tell you when the spring designs will ship.” I don’t think she heard my “Goodbye.” She was off, back into her bustling world. As I hung up the telephone, I hoped she took my gift, would use it often and remember the new experiences she had last night.


That same night, I had a text from Carla, “Would like to talk to you privately. Can I call you at home? When? Number?”

I texted back with my private cell number and suggested after eight p.m. or anytime on the weekends, “Will enjoy talking with you any time, any place; you are exciting and delightful but still a mystery.”

Carla was in California. It was ten p.m. on the east coast when my phone rang, “Is it too late to talk?”

“No, Beautiful, I don’t need to sleep, if I can talk to you.”

“Are you always like this?”

“You’ve worked with me on a purely business basis for three years, what do you think?”

“Ok, true, you have only been playful since the night I had to stay over in New York because my flight got canceled.”

“We do have complications because we have a working relationship and I am attracted to you? I’ll back off, if all this makes you uncomfortable. But, “Yes,” in my mind, I’m always sexually playful.”

“No, no, I don’t want you to back off, that’s not why I’m calling you. Our dinner, our play with the waitress and you, in general, put some much needed excitement back into my life.”

“Again, “put” is past tense. Talk to me. Ask me what you need to ask. It may be time we risked a little to discover some unknown possible beauty.”

“Matt, I enjoyed our dinner, your gift and spending time with you. I’m wondering where you are trying to lead me and if I can go there.”

“Carla, you are making too much out of the D/s thing. I’ve been married twice. The first one lasted twenty five years until Millie died. We had four kids and a good life. We had a good active, equal sex life and never even role played in the D/s lifestyle, other than maybe tying each other’s hands to a bed post. My second marriage lasted five years and was about the same sexually. Susan liked different things. I liked her creative naughty mind, but I couldn’t tolerate her affairs. The D/s thing came from a two year long relationship I had with a girl who wanted to go much further into the Lifestyle than I was willing to go. I can live with it or without it. I do enjoy the power exchanges, watching the far more intense climaxes of a woman who can let go enough to spiral into sub-space and her willingness not to hold back any part of herself from me. I’ve only had one such relationship.”

“What happened to that?”

“If I talk any more about this, we’ll have to be face to face and you’ll have to understand a little more about me. I’m a gentle but alpha male, who can be very physical and is fully capable of taking what I want but only from a willing partner.”

“You said you were oral. Can you talk about that?”

“That’s pretty self-explanatory.”

“I’m sorry, Matt, but to me it isn’t. I was married for a few years. I haven’t had kids. My ex-was a violent, abusive alcoholic. The relationship ended when he put me in the hospital. I’m over forty but I’ve worked and not dated. I’ve looked at the internet and talked with female friends but I don’t know what’s true or what’s exaggerated.”

“Damn, Carla, I wish I had known all that. I’m sorry. I’ve definitely done a lot of improper teasing and playing. If you can put all that behind us, I would like to start over. I am attracted to you, really enjoy your company and am hoping canlı casino we can date to learn more about each other. I’ve probably given you all the wrong ideas about me, frightened you and you only tolerate being around me because I’m an important customer.”

“That’s not the case at all. I’m attracted to you also. I’m intrigued and shocked about things that have happened. I would like it if we date. I just wanted you to know that I’m not experienced like you and …”

Her voice trailed off. “Carla we are friends now. You’ll learn I have some concerns and insecurities too. You can be open with me. You won’t shock me. Please, go ahead and finish what you were going to say.”

She beat around the bush a couple of times trying to find a way to open up. Her voice trembled. Finally she said, “All the women in your pictures are beautiful. From my ex, I have some ugly scars and permanent marks on my body. I would never be beautiful like that for you or any other man.”

I was quiet too long. She did not understand. I could barely talk. I said, “Carla, everything is fine but I have to call you back in a few minutes.”

My mind had flashed back to finding my first wife’s sister and years later having to identify my daughter’s body at the morgue. My body shook, I cried; I remembered; I pulled myself together; I practiced talking and I called Carla back.

“Sweet Thing, just listen, don’t say a word or I won’t be able to get through this. First, your scars will not make any difference to me; it is you I want to know. I might have some trouble but it won’t be you. I broke up and cried when you told me. When Millie and I got married we lived next to her older sister. One day, her sister did not answer the door. Millie said she could barely see her sister on the couch through the curtains. I broke in the door and found her beaten to death with a claw hammer. Twelve years ago, my daughter called after being beaten by her husband. I told her to come home. She was hurt more than I knew. She died in a car accident coming to me. Don’t ever be afraid of me. I can never hurt a woman. You might see me cry but your scars will not offend me. They too will be a horrible kind of beauty because they prove your strength over what you survived.”

Carla was quiet. I was too. I broke the impasse, “Carla, please call me tomorrow or when you can. Let’s start over. I need a wonderful, intelligent female friend like you. I really like you and hope things might grow between us. But let’s talk, maybe date when you are in town and see what happens.”

“I’d like that. I’ll call tomorrow.”

I could tell she was crying.

Carla and I burned up the telephone lines for a month. She’d even call me to tell me what she was having for lunch and I’d tell her I would probably still like her kisses even though she was eating onions. I knew everything from her shoe size to the stores in her home town. We were both nervous as teenagers on our first date when she made it back to New York and we went to dinner and then a play.

The next night we started earlier. It was before nine when she asked me to go up to her room with her and share some wine. We held hands and were even more nervous because we knew where this was leading. She had planned for me. After we talked for a while in the little sitting alcove in her room, she said she wanted to get into something other than her work clothes and hard shoes; her feet hurt. She adjusted the lights around the room and turned on a TV music channel, as she headed to the bathroom. I took off my shoes and tie. My coat was somewhere in the room.

Carla was blushing when she came out in the fluffy white bathrobe provided by the hotel. I could tell she had some kind of short thick cotton nightie under it. Now it was my turn – my turn, to at least claim her lips.

I met her in the middle of the floor and our first French kiss was hot, wet and passionate, like we had been lovers for years. I sat on a desk chair and pulled her to sit on my lap and kiss me again. Within seconds she knew what I was doing and she let the wetness in her mouth flow into mine. Her tastes exploded through all my taste buds. She relished me drinking from her and sought to give me more. She hovered over me, balancing by grasping my hard cock and letting me suck the wetness from her tongue as we worked one kiss into a sexual masterpiece of desire.

I was dizzy. My cock was rock hard and twisted in my slacks. Carla was as turned on as me. She threw her now too hot bathrobe onto the floor and straddled my hips. The moist heat from between her legs was shocking even though it was passing through her nightie, her panties, my slacks and my boxers. Her hips were searching for some friction for just the right spot. I challenged her, “Reach down into my slacks and pull my cock up straight so you can thrust into it.”

She might not have had many experiences but without hesitation she undid my slacks, slipped her right hand in my boxers, and rubbed her palm through the precum what was coming from me more freely than I ever remember. She reached to the base, let her fingers and thumb encircle me and pulled back half way up my cock and squeezed. Slowly I pulled my hips back, her fingers tightened and I pushed my cock through her tight fist forcing her fingers to spread.

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