๐Ÿ“š date-night Part 177 of 102
date-night-177
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Date Night 177

Date Night 177

by boomtastic69
20 min read
4.7 (3400 views)
adultfiction

Readers: This is part three of what is planned to be a four-part series. I love all the feedback and amazing suggestions on how the story could be progressed. Thanks for the encouragement and I hope you continue to enjoy the story.

(Her:) I had gotten cocky. I had tried to make a deal of silence with my husband for six months while I arranged a special threesome with a coworker, but he only agreed to three months of silence regarding the secret desires I had been keeping from him. I agreed to the deal believing I could accomplish this in just a couple of weeks. Three months either way would give me time to process the secrets I had shared with him and be ready for him diving into those desires with me. The result also being his fantasy of watching me eat out another woman. I had been teased by my co-worker Jess in the past who is very forward and I find myself attracted by her dominant nature.

I was not thrilled about the idea of being with Jess even though my man had encouraged me to pursue it on more than one occasion. The problem is I like his touch and how he holds me, how he caresses my body and kisses me. I love how he handles me in the bedroom and could never see a woman being able to accomplish the same level of electricity for me. Also, Jess was very clear on the fact that it was her intention to put me between her legs and I am more of a receiver, than a giver unless there is a stiff cock involved.

Jess is a knock-out and I know this because men stare at her 5'8 frame with a desire their eyes cannot hide. Coupled with her dark hair, olive skin she walks with the impression that she is dominate from the word go. I knew if we were naked in a room together she would have me on my knees and servicing her needs. This is just not what I have wanted to experience, but given my husband's sudden domination of me and the whirlwind of sexual fantasies which have followed us since those secrets were revealed, I honestly look forward to being made her bitch, instead of face his questions for a few more days.

Now sitting in the lunchroom absently looking for answers in my salad and thinking about my husband's subtle threat over breakfast I watched as my would-be savior casually strolled into the breakroom and opened the refrigerator.

When we made eye contact she scanned the room, then asked, "Having any luck?"

Being the only two in the room I sarcastically answered back " I didn't think I would need any luck, until you pulled the rug out from under me!"

Jess knew the bind she had put me in and approached my table with a sarcastic bottom lip and frown on her face, waiting for me to invite her to sit down. I gestured to the seat next to me and the frown was followed by her wicked smile. She definitely seemed to be enjoying my suffering. I can't really blame her given the teasing I had done and how I led her on since she joined the company a year ago.

HR would have had a field day with us if they had ever found out about our heavy petting sessions in the ladies room. One day she cornered me and told me exactly what she wanted me to do to her, but I was scared and backed away from her advances. She told me that she could see what I wanted and to come find her when I was ready. I had then worked hard to establish a line of friendship and ironically once the "friendship" line was drawn we became inseparable co-workers and really good friends. I had been thrown off by her aggressive nature and found it unsettling that a beautiful woman like her would be so dominant.

Jess never showed that side of herself to me again and with time she became a trusted friend and sounding board. Fast forward to today and she knows the whole situation with my husband. When I finally worked up the nerve to ask her to help me out, she rejected me. Saying we had worked too hard for our friendship and she did not want to jeopardize it, but I pressed her and she confessed that she was currently in a relationship.

Three months to ask her should have been no big deal, but I procrastinated for weeks before bringing the opportunity for joining us for some adult fun because I knew it would mean I would find myself between her legs. I wanted to invite someone who I could make pleasure me, pleasure my husband, and then watch as he made her cum. I did not want to start by being my best friend who is also a trusted co-worker's little bitch.

I knew Jess had been involved with someone for several months, but did not realize she had made it a monogamous relationship with them. This was a very big deal for this free-spirited woman who had said she would never be willing to settle in a trapped sexual relationship with one partner, to suddenly inform me that this was where she was today, shocked me and also caused me a lot of issues.

I did this to myself and with only two weeks left before the deadline I was in real trouble and it was my own fault. I had all but surrendered to the idea of my husband tying me up and torturing me as badly as he had months earlier. It both excited me and terrified me. At this point I would have preferred to have to lick pussy juices from my lips to the alternative my husband had planned.

(Him:) I had nothing planned. My wife was running out of time and I can see it in her eyes that she is scrambling to find a solution. Something has not work out for her in the last few days as her confidence has faded and she looks concerned when I mention being excited about our special night. When she had everything in hand she was playfully teasing me about the day, but this last week she has been cold and avoids the playful teasing. I added a little pressure to the situation by circling the three-month anniversary of the date on the calendar in the kitchen and wrote in the small square the words "Date Night". I know she has seen the date circled on the calendar and she is not being playful with me when I catch her looking at it.

She had shared her deepest darkest secrets with me and made promise my silence about them for the past three months. When she told me her desires it made me speechless at the time, but I have since found my voice. The fact that I spent hours torturing her for her to finally reveal to me that she wants to see me sucking a real cock and being fucked in the ass leaves a lot of room for conversations.

My original goal was to push her to see if there was anything after 30 years of marriage that she had wanted that I was not providing. She loves to walk into the room in a skimpy outfit and say, "What ya gonna do with me?" She is a submissive sexy woman who just wants to be fucked. For 30 years I found different ways to bring her pleasure, but the last year or two I got the feeling she was hiding something. It was the way she orgasmed. She would close her eyes and would disappear into her mind. Usually, her climaxes would be with her eyes open staring at me, but then she started closing her eyes and it seemed she was thinking about something that brought a flush to her face and chest like I rarely see in our sessions. I wanted to know what she was imagining. I guess ignorance is bliss, but I was determined to get her to tell me, even if it is something I can't quite understand.

I was shocked, but what had plagued my mind was the thought of her wanting something for her satisfaction, not to see me having sex with another man. My wife is not a visual lover, she is a touchy feely type. So, this really altered my view of what I knew about the desires of this woman I have known my whole adult life. So, to understand her better and because I was not allowed to talk to her about it, I did the next best thing. I started to dig into her internet searches to see what she had been up to.

She had never been big into porn again she liked the physical touch, not the visual stimulation. She had no issue with me watching porn and did not feel insecure about what I would watch. I start reviewing her history and found typed searches like "make him suck cock" and "Bi sex threesome". This led me to a site she visited often. Once there I started watching the video's she had favorited. They all followed similar themes. The woman was encouraging a man to suck another man's cock. Then I watched two women and a man, before realizing the third woman was actually a shemale.

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I noticed that as I watched this video I started to get aroused. It looked just like so many pegging videos we had watched together, except when the couple was between her legs, they were sucking on a cock. I found myself stroking myself thinking about her darkest desires. She had a few videos of cuckold hotwifes where the woman forced her man to suck on another man's cock. This was enticing to think of her taking charge like that for a change, but I lost interest at the thought of getting on my knees in front of another dude.....I just couldn't get past it, until I reached her favorited shemale clips where beautiful shemales were fucking the guy, it looked so much like pegging that I was entranced on the beautiful woman with big tits and a cock. These clips made me rock hard. I wanted to talk with her about her favorited clips, I wanted to understand where her head was at, but I promised not to mention any of it for three months.....

Honestly, I was going to have a hard time making it the next two weeks without saying anything to her. It did not make it any easier knowing she was not going to have plans for our date night.

This morning as she got ready for work I whispered playfully in her ear. "I'm soooo looking forward to our date night. Don't worry if you don't have any plans my love, my bondage session with you three months ago was just a warm-up, just wait until you see what I have planned....."

(Her:) "I don't know what to do, Jess." "I have tried to find anything that did not smell like a scam or a disease waiting to happen! I have looked at escorts, the local Backpage and even weekend trips to Las Vegas, but all of it is too late. I only have two weeks!", she told her friend in a frustrated tone.

Jess looked at her and smiled saying "Well, I might be able to help you out, but you would need to meet her and she would have to agree."

I looked at her shocked. "What are you saying right now?"

Jess continued " I have a friend who, ironically, is interested in having fun with me and frustrated that I am not available. She knows your situation and wants to meet with you to see if you are a good fit." I smiled and had a million questions, but Jess stopped me saying "Listen, she is a woman of particular tastes, she is very demanding and I will warn you that if you accept her offer you will be calling her "Mistress". I know how you feel about domination, so I have not offered this to you until now. If you want to meet her I have an invitation from her with her instructions for you to follow and I will warn you that she will test your limits. I know she tested mine....."

All I saw was a ray of hope and barely heard her warnings. A solution to this terrible situation and I quickly agreed to meet her. As long as she was not a hideous troll I did not mind calling her "Mistress". I secretly enjoyed calling husband my "Master", even though he rarely made me do it. I was sure I would be able to negotiate with her once I shared my situation with her. It would be easy once we could talk, just us girls. "I am in! Where does she want to meet?"

Jess slide a sealed envelope with my name on it over to me and said "Here is the address and what she expects of you. Believe me, she will check to ensure you follow her instructions to the letter."

I come from a small town in the mid-west with conservative parents and I was raised to be a good girl. Then I discovered college and when I met my husband I was well on my way to experimenting with all kinds of life's adult distractions and sex was my favorite distraction. I was a good girl, but only in a way a boyfriend or husband can appreciate. I blame him for my wicked nature since he introduced me to porn, pegging, and anal. However, the look on his face a couple months ago had to be similar to the look on my face when he told me he wanted to stick his big dick in my little ass. I blew his mind. He discovered that these thoughts of mine came from my own deviant spicey soul. I had been quite proud of being able to one up my husband after all this time and our myriad adventures in our sex playland.

Even with all of that when I opened the letter, which appeared to be a wedding invitation, rather than directions for a luncheon.....It took my breath away. The note was written in an elaborate cursive almost calligraphy style gold embossed print and said:

You are cordially invited to join me for lunch tomorrow at 1pm.

You are expected to be freshly shaven and clean. Do not wear any type of body spray or perfume.

You are to wear a shear white top with a black lacey bra.

Your skirt must be no less than four inches above your knees and you must be wearing heels with at least three inches.

You may wear crouch-less panties, if you must, but I discourage this distraction from our meeting. It is preferred you wear no panties at all. And your pantyhose must have a seam which goes straight up the back of your legs.

Our lunch date will last precisely 45 minutes. I will order your lunch and it will be delivered to our table at precisely 1:03 PM, if you arrive 5 minutes late you will be invited to leave. If you arrive more than five minutes early you will be invited to leave.

I will inform you of the preparations required for the planned event. I will control the activities and flow of the entire session.

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If this arrangement does not appeal to you, feel free to disregard this invitation.

MH

MH? Finally, catching my breath, I asked looking at Jess.

Jess smiled and said "You will have to make the meeting to find out. All I can tell you is that you need to take everything in that letter very seriously."

I was in shock saying "Well you have met her, what kind of woman is she, what does she look like? How do I not ask her questions!"

She then got up and smiled saying "I can't help you answer these questions, but if you want to swing by my apartment before the meeting I can make sure you have everything on the way she likes it. Back to work....Good luck!"

I looked again at the invitation and back as Jess left the breakroom. Was I being punked? I was not quite sure if Jess was waiting to come back around the corner and say "Gotcha!", but that never happened. In fact, Jess refused to talk to me about it for the rest of the day. She remained very cagy and just told me that she needed to stay completely out of making the decision and had to let me make up my own mind based on the invitation. I had already decided to meet MH, but I needed a few things from the list, so I took the afternoon off to go shopping and hoped this was not all just a big waste of time. Of course, I reminded myself that this was my only possible solution, so it was not a waste of time either way.

(Him): Yesterday she came home from shopping with a bit of a spring in her step and today she left the house just before noon for a lunch appointment she told me was at 1pm, but her attire was not the typical business casual dress as she hurriedly put on an overcoat to try and hide her outfit. It looked more like she needed to head to our bedroom or was planning on providing escort services to someone. I asked her if I needed to be concerned about her finding a lover as I eyed the lacey bra through her shear white blouse. She responded that this was just her getting things ready for our date night and that I was not allowed to touch or to ask any more questions!

She looked so irresistibly hot! I put up my hands up and slowly backed away while she tied up her overcoat and eyeing her from head to toe saying "Well, ya gotta come home sometime." I did not even know she owned heels and stockings like what she had on. I reminded myself that she would need to explain this to me and that outfit needed to make it into the bedroom wardrobe rotation. Since she was gone for at least two or three hours I decided to keep myself busy with her browser history and see what she had been up to and how far back these desires had been recorded in her browser. She kissed me passionately and was on her way.

She is a talker so it would be at least two hours before I was disturbed. I wanted to know how far back this desire of hers went. I did some simple searches and found that these fetishes of hers had started a couple years after she had got comfortable with the idea of wearing a strap-on. It was awkward for her and challenging for me because she was really not into it and was reluctant to wear it unless I asked her specifically to put it on. After a year or so, she told me she enjoyed sticking it in my mouth and fucking me with it. She liked to make me feel the same things she feels when I put her on her hands and knees. It looks like that fetish branched out into other searches starting with pegging threesomes, moving on to cuckolding, female domination, and now a lot of searches are centered around MMF and trans.

Now I understand why she wants to see me get fucked and to be honest some of the clips of shemales she has saved were a real turn-on and I tried to stop before I got too excited. I wanted to have something for her when she got home. Then I came across a folder called "FantasyPlans".

(Her:) Jess was a god send. I had left early to have her give me the once over before my lunch. She was surprisingly super critical of my outfit and how I had prepared for the luncheon. She was even extremely picky about the seam on my pantyhose! She told me to take off my bra and went and got one that she called "more appropriate". I would not even classify what she handed me as a bra!

At one point she pulled out clippers to clip away some wild pussy hairs I had missed and asked me if I was taking this meeting seriously. She was being stern and matter of fact, while it should have been a turn on having her on her knees clipping the few wild hairs, it oddly, was very sterile and not sexual at all. After her inspection and corrections, she hurried me out the door, so I would be on time.

I looked at my watch as I approached the maรฎtre d and realized I was going to ask if "MH" had arrived, but before I could ask she looked at her watch, smiled, and offered to take my jacket. She then told me my party was waiting for my arrival. As she led me through the dimly lit restaurant I noted that all the tables were empty and said, "Not much of a lunch rush here is there?"

She turned and smiled saying "We are only open for dinner with the exception of special occasions."

I had researched the restaurant and it had a three-month waiting list for dinner reservations, with no lunch menu online and no hours of operation. It seemed a bit odd, but here I was approaching the table in the very center of the restaurant, fine linens, crystal stem ware and the back of what appeared to be a slender woman with jet black hair. As we approached the table the waiters were placing the plates at each place setting. Glancing at my watch it was 1:03 precisely. The maรฎtre d escorted me to my seat, but stop short of pulling out my chair for me.

The woman was gorgeous, still sitting in her chair and smiled at me saying "Well, Jess was not exaggerating, my dear. You are a stunner. Then looking at the other woman she said, "But did she follow my instructions?"

I opened my mouth and she held up two fingers to stop me. She then gestured to the woman behind me saying "I was not asking you. Don't move." The manager got down on her knees and measured the hem on my skirt saying, "Five inched above the knee." I then felt her hold each foot saying, "Three and a half on the heels." She then traced two fingers along either side of the seam on the back of my stockings saying, "The seams are within your tolerances, mistress." This caused MH to raise an eyebrow and look at me with some skepticism, but she did not say what was on her mind.

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