My Wife's First Time Ch. 08

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I go on my first date with customers from my website.
11.2k words
3.67
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Part 8 of the 8 part series

Updated 12/15/2023
Created 06/05/2022
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I have been coming to Literotica for a long time. So, I decided to post some of the many stories I wrote to kill time in my retirement. My stories are only fantasies about sharing my wife, and they are only my fantasies and nothing more. I would love to watch my wife have orgasms given by another person. It is the most beautiful thing to watch her face change from a look of passion and lust and then see that look of joy when one racks through her body.

I would love constructive criticism about my writing. But all the anonymous assholes who come by with them thinking they are schoolteachers or bible thumpers make me wonder why I am doing this. I do not need comments from those with a problem with this type of lifestyle. Let's face it; if you come to Literotica, it is to read erotic stories, so enjoy them. Don't cut up the people who like to read or write them if you don't like wife-swapping, wife-sharing, girl-on-girl, male-on-male, hot wife, or wife prostitution. Please do not read this story. Move on. You have been warned. Also, be warned that if you leave comments that ridicule or mock the characters in my stories and lifestyle, I will remove them.

My name is Jan. I'm 48 years old and work as an office manager for a large downtown Hartford corporation with five different divisions. I do very well for myself, as does my husband, and we have no children. Except for a small mortgage, we are debt-free. We both have advanced degrees in our fields.

In college, I was a cheerleader, and I enjoyed getting the attention of a gym full of men watching us do our routines. I was not one of the small, skinny girls. I had a larger frame and was almost six feet tall. But boy, was I gifted with a pretty face and a well-proportioned body. (My husband refers to me as his smoking hot wife.) back in high school, I had and still have 38 D breasts; not to brag, but they have never sagged. (Due to all my hard work in the gym.) But they have a slight jiggle in them, the set of tits that a man has difficulty looking me in the eye while talking with me. It probably doesn't help that I flaunt them by wearing low-cut blouses. I also have long, full, silky chestnut brown hair flowing down to the middle of my back, bouncing back and forth as I walk. I have a smaller waist and legs that go on forever, so I'm told. They are toned from wearing high heels most of the time. The only time I don't wear heels is when I run every evening.

Men still stop and look when I pass them (Why Wouldn't They). I shake my ass a little extra to give them a show if I am aware of their gawking. I can still do a split at my age, and I do yoga at least three times a week to keep a supple body. I love wearing lingerie under my business suits and, for that matter, under my slacks and jeans. You could say I am addicted to the feel of real silk touching my body. That was my only vice in life until I lived out one of my husband's fantasies. I am now what you would call a hot wife, and I love pleasing other well-endowed men in front of my better half for both of our enjoyment.

Some people may think he is a cuckold, but I do not humiliate him; what I do, he knows beforehand. If not, I will tell him all about it soon after. He wants it as much or more than I do. He sets rules if he is in the room when we bring someone home. He tells them: "Rule One is NO means NO. Two, do not ever humiliate her or me. Three: if you hurt her, I'll kill you. So, she is a very sexy woman. Enjoy her."

We make satisfying love almost every day. I have made it a point to bring all my men home to our bed and tape our sessions if he is not with me. He watches the tapes and picks up on points that make me have a larger-than-normal orgasm and uses that info in our lovemaking sessions. If you think he sets in a corner and jerks his little prick off while he watches, the answer is no. Frank has self-control and waits for me to clean up, and then when I am ready, we make love as we reconnect; by the way, any size queen would pick him first if she had a chance at a wife-swapping party, and I have to fight the women off of him.

Now to. My First Time with Another Man Pt8

I go on my first date with customers from my website.

Frank and I check my escort website often. We have not found any clients we can agree on. From the very start, we agreed that we would both have to feel good about the persons with whom I would date, and we could feel safe with them. One of the important things we wanted was for them to supply an up-to-date lab test to be filed at the time of their request and another one on the night of our date. I had five-star reviews from Richard, James, Buck, Carol, Kathy, and Easy.

Things changed one Thursday night when we checked out the website. There was a request for a date with a couple. They supplied a lab test for each of them and filled out all the information we wanted. He was fifty-two, and she was fifty-three. He was a lawyer, and she owned an interior decorating company. In their request for a date, they asked if I would see couples because I had not said on the website that I did. I had only said that I would see males and females and would definitely not see multiple men on the same date or do stag parties.

They also supplied pictures that were not needed in this part of the interview process. The male was tall, maybe six-two or maybe a little taller. Well-kept black hair that was starting to gray just a little. A squared jawline with a five o'clock shadow, something that always gets points from me. The next thing that got my attention was that he was wearing tight biker shorts, and I could see an outline of a very nice size cock in them.

I was intently looking at that until Frank broke me out of my trance when he said, "He has a nice six-pack, right Jan?"

"Oh, sorry."

Then I noticed he was not wearing a shirt. It was over his shoulder. He had a broad chest that was chiseled from working out, not quite like a bodybuilder but very nice, just the same. His chest tapered to a well-defined six-pack, and his waist was probably around thirty-four inches. Moving down to his thighs, they looked like they came from many miles of bike riding, a lot of running, and many laps in the pool.

Overall, he was one fine specimen of a male. Frank saw the lust in my eyes, clicked on the woman's picture, and opened it.

Wow, her picture was from a boudoir photo session. She also appeared to be tall. Her makeup was meticulously done, showing off her piercing blue eyes. Her hair was dark blond with lighter blond highlights that were tastefully done. It hung over her right shoulder while lying on a bright red lounge chair. The hair hanging over her shoulder showed her long, sexy neck, which sported a fresh hickey. Frank commented whether the husband or the photographer had given it to her.

We were now looking at her thirty-six C breasts, and I told Frank that they were real, and he said he thought they were too perfect and manufactured because they had a slight upturn to the heavens. She wore a matching bright red lace half-cup bra that left half of her areola above the bra; the very large nipples were pushing the material up so you could see just the tops of the nipples. Then, when you traveled down, she had a very sexy woman's six-pack. She had on matching bright red lace French-cut panties pulled tight against her camel toe; you could see through the lace and could tell that she was bald as the day she was born. The high-cut panties showed off her shapely hips and thighs that were just as toned as her husband's.

The third picture was taken with both standing next to a silver Bentley. He was in what Frank said was a two-thousand-dollar dark blue Italian suit tailored to his body, and she was in an ankle-length evening dress made of light blue silk. There was no way that she could have had on any panties because the lines would have been seen. Plus, she had no bra, and the back was open to the top of her killer ass.

I pulled up all three pictures and looked at them side by side while Frank was out of the room. Frank returned when I was about to put my hand inside my shorts. He noticed how intently I was looking at the pictures and could also see the lust in my eyes.

He shut down the computer; I was broken from my trance when he took my hand and said,

"That is enough for tonight. Let's go to bed."

Walking to the bedroom, I asked, "What did you think about them?"

He answered, "I think they are a very sexy couple, but I also think I might get a little jealous if you took the date, and I would not be able to be with you."

I stopped just inside the bedroom and looked deep into his eyes. I could see the trepidation he was having.

I said, "OK, I will let them know I do not take dates with couples."

He went into the bathroom and showered without saying another word to me. I know I had something I wanted to say about his sudden 180-degree turn-around about me being with another man. He also looked like he had a lot to say about it also.

I then went into my lingerie drawer and took out the purple bag, his favorite color. I put on the camisole and panties, no bra, and left the matching color boxers out for him. I left, entered the family room, and turned on the TV to watch the late news. After watching the local and national news, he still had not come in to talk, so I went to the master only to find him not in bed and had not even put on the boxers. I checked the spare bedrooms and found him in one with his bottle of sleeping pills and half a glass of water on the nightstand.

I leaned over, kissed his head, and said, "I love you more than you will ever know."

With that, I went into the office and opened the website. I had learned enough to pull the site down for repairs and did it. I then called and left a message for my assistant and told her I would not be in tomorrow. Then called Sara's Phone, which went right to voice mail, told her Frank would not be in tomorrow, and asked if he had any appointments to cancel them or take care of them herself. Then wrote a note to Frank and left it under his cell phone that was charging in the office.

The note read.

Frank, I love you more than you will ever know. I have taken today off and called Sara to tell her to cancel any appointments you may have had. We will sit down and talk about the elephant in the room and settle everything once and for all. I have also taken the website offline because it may be a big part of this problem, whatever it may be. We will not leave this house before we solve this once and for all.

Love Jan

PS. I hope that when I wake, you have put on your purple boxers and are ready to make love to me the way I wanted to last night before you ghosted me. When we are done, we will talk.

I woke to the bed being shaken as Frank climbed in. He spooned against me, and I could feel he had put on the silk boxers. He put an arm over me and pulled me tight up against him.

I asked, "Are you ok, Frank?"

"Yes, please be quiet, and we can make love and talk later."

His left hand came up and lightly squeezed my breast and nipple.

I rolled over and said, "No, Frank, I have decided to talk first, and then the makeup sex will be much more fabulous."

I paused and then said, "Frank, talk to me. Why did you ghost me like you did last night? I told you I would not take the date."

"I got scared; they looked like a power couple, that they could just take you away from me forever. They oozed the feeling of wealth beyond my conception like they could buy whatever they wanted."

I asked, "Frank, why don't you feel that way about Richard? His net worth is approaching half a billion dollars. You have never worried when he sends a limo from New York City to pick me up for a three-day date? As a matter of fact, Frank, the last two times I went down to see him, you stopped asking me what we did, and if you think that I did not know that Sara, Annette, and you played around the whole time I was in New York City those two times, you might be wrong." So that you know, I refused a two-week trip to Rio with him just because I knew that would not be the right thing to do."

He started to say, "I don't feel threatened by Richard."

Before he could finish, I cut him off. "You should be because he is a tiny bit below you on my list of skilled lovers and richer than you can believe. Could you afford to take me to Rio for fashion week and promise to buy me the latest fashions before they hit the shelves? I think not?"

His face dropped, and he said, "Jan, that stung."

"It was meant to, Frank, so tell me why I am here now. Why? Because. You are my husband, and I love you more than anything. Here is another thing you should know, Frank: on the last trip down to see Richard, we went to the car show at the Jacob Javits Center; he introduced me to Chip Fosse, and I was going to use the money from my dates to have him turn your 55 into a showpiece. On top of that, he plans to do it at SEMA this year for his show. That's how much I love you, you pig-headed fool."

His head fell so that he was no longer looking directly at me, and a tear fell from his eyes.

He said, "I had no idea, my love; how could I have ever doubted your love for me."

I put a finger under his jaw, brought his head up to look straight at me, and said, "I don't know, Frank, but you have been the world to me. I hope you will continue to be my universe for the rest of our lives."

"I Know this may not be enough, but I am so sorry for thinking someone could take you from me. Jan, I love you more than life itself. After seeing how sexy they looked, I was jealous that you would have all the fun and I would be left out. I know you will have a nice time when you finally take that date. Jan, please break protocol and don't go through the next steps online, so call them and meet them someplace to see if all of you connect. But if you can, please have them come here so I can watch it later."

Then he moved towards me. I thought he would kiss me, but he brought his mouth next to my ear and softly whispered, "I love you." Then started licking all around it. When he finally inserted his tongue inside my ear canal, my juices started to flow all at once. I pushed my head into his shoulder and started to moan and surrender my body to him. From past experiences with Frank, if I became submissive, he would give me immense pleasure, which is exactly what I needed and wanted.

He would not be disappointed this time, either. He held my head in place with his left arm while kissing and licking my ear and neck while he used his right hand to run the back of his fingertips across my body with a feather-light touch. The light touch sent little shivers through my whole body. To make the pleasure much better, as the tip of his finger passed over me, I would get goosebumps in that area only to fade away but follow the path of his fingers. My love canal was emitting a flow of hot juices over his thigh that was pressed against it the whole time.

I moaned into his shoulder. Then I said, "How can you find new ways to turn this body into a quivering mass of jelly? Oh god, please don't stop. I so need you to send me to my happy place."

He then pushed his finger between his thigh and my smoldering snatch. The quick touch gave me my first small orgasm. I hoped he would finger me to a grand one, but he just coated his fingers, brought them up to my face, coated my lips, and then kissed me so deeply I thought he was trying to touch my tonsils with his tongue.

I felt my clit get hard and pop out of its hood. I started to hump Frank's thigh to see if I could get some relief. He broke the kiss, leaned back, and watched my face as I pleasured myself, humping his leg. One of his favorite things was to watch me masturbate, and that is what I was doing. He pushed his thigh tighter against my leaking pussy, and I was delighted. The sensation of his hairy thigh running across my super sensitive clit sent tiny little spasms through my body, and I was lost in lust and my desire to have the mother of all orgasms.

I lost all conception of time as I pleasured myself and tried to bring myself closer to the orgasm I so badly wanted. I just continued as I said, "I love you, Frank. Thank you for letting me do this. I'm close. Oh my god, I am so close." I then reached up and started to play with my nipples. I was pulling and twisting them rhythmically with my humping on Frank's hairy thigh.

Frank watched in delight at my actions, then took his hand, closed his fingers like a cup, placed it just under our thighs, and waited for my hot, dripping juices to get full. Then he brought it up and let the hot juices drip over my fingers to coat them and my extra hard nipples. This was all I could take, and I had a massive orgasm. I had never been to my happy place from masturbating, but I guess the thrill of doing this, with him being involved, triggered me, too. I passed out after I shot a massive amount of cum over Frank's thigh. I dreamed of how wonderful it felt to show off to my loving husband in my happy place.

Frank never tried to do anything to me while I was vulnerable and in my happy place. The most he would do was clean me. But today, Frank rolled me onto my left side and spooned me with his rock-hard cock nestled in my ass cheeks. I was somewhat aware that his instrument of pleasure was close to where it needed to be. Unaware of what I was doing as I dreamed, I rotated my bottom so that his hard-on slipped between my thighs to get it close to my intimate place.

I squeezed my thighs together, and his hard-on made contact with my still-hot pussy lips. With another squeeze, he was captured between my slick lips. Just then, Frank changed his position, and the head of my desire was at the opening of my pussy. He slowly pushed forward, entering me, just the head at first. Then he slowly pushed inside me, and I mean it very slowly and tenderly.

He told me later that he knew he should not have done it, but Frank was too aroused. It seemed as if it took forever to get inside of me all the way. When he was buried deep in my smoldering box and touching my cervix, I started using my kegel muscles to massage his torrid cock. As I did that, he used his thumb to run little circles in the dimple on my back just above my ass crack. From our past lovemaking, he knew that that would make me rotate my ass.

His pre-cum was flowing steadily out onto my cervix. In my dream state, I whimpered, "Yes, lover fuck me passionately; please, I want you to give me another wonderful orgasm while you are bumping onto my cervix." I could sense he was close, so; I released my muscles' death grip on his torrid dick. He fuck me with long, tender strokes, and when he finally grunted out his orgasm, he pushed in all of the ways and shot six loads of hot cum right at the entrance to my cervix. Even in my dream state, it was too much for me, and I climaxed right along with him. We both fell asleep as the waves of pleasure passed through our bodies.

We woke up mid-morning and showered together. After breakfast, we went into our home office and brought the website up, and Frank changed it; in the info section, it now said, 'I accept dates with men, women, and couples if they can pass my screening process.

I sent an e-mail to the couple that was seeking a date.

From: A Moment In Time Escort Agency.

RE: Your requested date with Erica.

Please call me at your earliest convenience. 860-524-8123 so you can ask any question you might have. The one question I have is how you came upon my website. I am available at any time this weekend.

Hope to hear from you soon.

Erica.

The phone number was a phone we picked up from QVC and used strictly for website dates. Frank pulled it from the drawer and plugged it in to charge. About forty-five minutes later, it rang.