My Wife's First Time Ch. 04

How Jan Turned a Gay Man Straight.

Hi, I use LibreOffice to write and spell check. In the beginning, I thought it would catch my grammar and spelling mistakes, but I was wrong. As they say, I'm BAD, sorry for the grammar in my first story. Hopefully, they will let me re-post it without as many mistakes someday. Now for first-time writers I would suggest getting Grammarly, it is a free download and it will suggest changes for spelling and grammar.

I have been coming to Literotica for a long time. So I decided to post some of the many stories I have written for myself to kill time in my retirement. My stories so far are only fantasies about sharing my wife, and they are only fantasies. I would love to be able 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 to see the look of joy when one of them racks through her body.

I would love constructive criticism about my writing. What I don't need is comments from the people that have a problem with this lifestyle. Let's face it, if you come to Literotica, it is to read sexy stories, so enjoy them. Don't cut up the people that like to read or write them. If you don't like wife swapping or sharing. Then Please don't read my stories and move on.

Jan Gets Offered A Part Time Job

My name is Jan. I'm 48 years old and I work as an office manager for a large corporation in downtown Hartford.

I do very well for myself as does my husband and we have no children.

Accept for a mortgage, we are debt free. We both have advanced degrees in our fields.

When I was in college I was a cheerleader, and I enjoyed the attention of a gym full of men watching me do our routines. I was not one of the small skinny girls, I have a larger frame and I am 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.) I had and still have 38 D breast, not to brag but they have never sagged. But they have just a slight little jiggle in them, 'you know the set of tits that a man has a hard time looking me in the eye while talking to me. It probably doesn't help that I flaunt them by wearing low-cut blouses. I also have long full silky chestnut brown hair that flows down to the middle of my back and it bounces back and forth as I walk. I have a smaller waist and; legs that go on forever and 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). If I am aware I shake my ass a little bit extra to give them a show. At my age, I can still do a split 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. I guess 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 guess 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 our enjoyment.

About a week ago I started working part-time for an escort agency. You could not have asked for a better date than my first date. Richard was a very experienced lover and we ended up spending the entire weekend together. He took me to the casino and other than that we spent most of the weekend in bed pleasing each other. Besides a weekend of great sex, it ended up being very lucrative. I had told the owner of the agency I would work on either a Friday or a Saturday night because I work a full-time job. But it was to my surprise that Evette call and asked me to work the next Thursday night to escort a gentleman to a fundraiser as his eye candy.

She did not have any girls that met the gentleman's requirements. He was looking for a sexy mature woman with large breasts that would not be afraid to show them off and that would draw attention to him and his date. He wanted everyone at the event to see him with a beautiful busty mature woman. Evette told me I would only have to work for about six hours and that it would include a nice dinner an auction and some dancing that is if he decided to stay for the dancing. She also said I did not have to worry about having sex because he was gay, and had not come out yet, but that I would have to sign a nondisclosure form stating I would not sell or leak that information because he was a well know in our area. She also told me that it would pay One thousand dollars and I should be home before midnight. Frank was still out of town so I accepted the date. I called Frank real quick to let him know that I would not be home that night and that I would see him on Saturday afternoon at the airport.

I left work an hour early, and as soon as I got home from work I showered and did my hair and makeup. I checked myself out in the full-length mirror in the bedroom in my birthday suit. I thought the extra couple of miles a night in my run had done some good and that I looked fantastic, it was a shame to be showing it off to a guy that would have no intention of trying to get me in bed.

I put on my thin black silk and lace garter belt, stockings, and panties then found a long flowing thin black silk evening dress that was open in the back almost right down to the crack of my ass and had a cress cross pattern in the front that went across my 38 D breast just barely covering them. You could see my nipples standing out. It also had a slit up the left side all the way to halfway up my hip. It was the type of dress you would see starlets wear walking down the red carpet. Evette had ordered me an Uber to bring me to the hotel, the driver was a female and her eyes popped wide open when she saw me. She gave me my invitation to get in and told me I looked stunning in my dress. I heard her mumble under her breath "God, She looks good enough to eat!"

I said, "If I swang both ways I would take you up on that."

She apologized and said "Sorry I did not realize I said that out loud."

"Don't be I took it as a compliment," I said as I smiled and winked at her.

I was dropped off at the entrance to the special function hall where I met Evette and my date, I recognized him from being on TV. He was very pleasant and escorted me to the bar where we had a drink. He told me that if anyone should ask how we met, it was through a friend of his and her name was Mary and we have been seeing each other for a few months. We took our drinks and walked around looking at the items that were up for the silent auction.

I stopped and admired a few things that I liked and after I passed them he would drop a slip in the glass vase that held bids on the items. We stopped and chatted with some people he knew and I steered him away from the CEO of my company just in case he might have seen me around our building.

At one point I felt his hand on my back as he spoke with some friends. I slipped my arm around him and he looked at me and smiled and pulled me a little closer. At that point, we went over to a corner and were people-watching, and his hand got a little freaky and slipped down onto my ass. I was surprised. I looked up and smiled at him to let him know I was OK with what he was doing.

He said "Jan tonight will do a lot for my image. Some people were going to call me out for being gay. Maybe after being seen with such a beautiful woman, it will all go away for a little while."

I looked up at him and said, "Maybe this will help." and reached up and pulled his head to mine and kissed him just as a photographer was taking our picture. At first, our lips just touched then he got into it and kissed me back. When we broke the kiss his head was just hanging down and he was looking down my dress at my breast. I took a finger and moved his face up to look me in the eyes. I asked. "Are you alright?" "Yes, Jan I'm alright. That was the first time in my life that I ever 'kissed' a woman other than my mother, except for those silly spin the bottle games in school." He said. "How was it compared to all the other kissing you have done male or female? I asked. I can't explain it. When I kiss my current boyfriend, it's like it is for effect and I have to do it. That kiss with you, I could feel emotions running through my body." he said.

"Which one do you enjoy more," I asked.

He pulled me close and kissed me again this time with more passion and after a little while I slipped him some tongue and he opened his mouth and he kissed me like a man that was trying to get laid. He slipped his left hand down the opening in the back of my dress and he was groping my ass pushing our crouches together. When we finally brook the kiss. I asked "Well?"

"I like this much better," He said. With a big smile on his face.

"Are you enjoying touching my ass?" I asked.

With his head hanging like a little boy that had got caught with his hand in a cookie jar he said: "Yes It feels so different."

"How different?"

He looked at me with a glaze in his eyes and said: "First It's so smooth, firm but very sexy!"

"Do you realize you are showing some effects of being close to a woman?" I asked

"What?"

I slipped my hand down and started running it on the inside of his leg and his dick was hard and still growing. I said, "Like this!"

Then I said, "You made my day sweetheart."

"Why is that?" he asked

"My body has brought you from being just plain gay to maybe being bi," I said

Just then an announcement was made that spoiled my fun. It was that dinner was ready and we all move into the banquet hall. He lead me to the table with his hand on my ass as if he owned me, and he did for the next four hours. We were seated with a group of high-class yuppies our age. All the men left to get us some drinks from the bar in the other room. I guess

to let the women get to know each other.

One of the uptight bitches asked me; "So Jan who did you go to, to have your boobs done they look so perfect?"

I answered, "Oh I had the best man for the job." I paused then said, "God gave them to me at birth and a bunch of hard work in the weight room and yoga mat have kept them nice and firm. Why who did yours?"

All the rest of the women laughed out loud at her and she never talked to me the rest of the night, no great loss. All the men and I had the prime rib and the pretentious women had rubber chicken and a salad. During dinner, they call out the winners of the silent auction. My date's name was called and they brought him his prize. It was something I stopped and admired, it was a beautiful fancy jade necklace. He put it around my neck and kissed me in front of all the people at the table.

While we were eating they changed the reception hall into a dance hall with tables and chairs around the outside. The same small cover band that played in the lounge on the weekend was there. They opened the doors separating the dining hall and the dance floor. I had enough of the pretentious women and asked my date if we could get a table on the dance floor to finish our drinks.

When we walked In and we found a small table in the far back corner. I sat down and pulled the open slit from the side of my dress over my legs revealing the straps from my garter belt along with letting the tops of the stockings show. His eyes popped out of his head when he saw my tanned toned leg. As he was staring at my leg I asked: "Would you like me to cover it up, if it's too much for you and your image I will?"

"No please don't." He said as he ran his hand up and down my stocking-covered leg. He touched it very tenderly. With his other hand, he pulled my head over and started kissing me again.

I stopped the kiss and sighed and said, "Let's go outside for a walk and get some fresh air, I don't know if it's hot in here or it's you are turning me on but I need to cool down."

He moved his hand up my leg it was now above the stocking, almost to the promised land, and was tenderly rubbing the skin above my stocking and very close to my damp panties.

He just looked into my eyes.

I said, "You are about to touch my panties and I have a feeling that once you do it, it will change your life for the foreseeable future." I paused with a deep sighed and said, "Maybe we should go to my place and take it slow and you can enjoy your first time with a woman."

He said "I would like that very much I have never felt like this with a woman before. But could you please be patient with me and teach me what to do?"

I pushed his hand way up my thighs to my panties, and then pushed his index finger into my sobbing wet slit, along with my panties, and slowly pushed them right up and inside of me.

I said in a very labored voice, "Your instincts will do most of that for you. I'll just teach you the finer points."

I called the Uber driver that brought me and she was right outside so I told her I would be right out.

Evette was in the lobby and I told her we were going to my place and I would let the agency know when he leaves. She took my date to a quiet part of the lobby and informed him that he had hired me as eye candy and that what he was about to do was a different price. He agreed with the new price and we got in the car and were off to my place in no time. I had the driver pull all the way up the driveway so the large bushes would block us from the neighbor's view.

We enter the house and I led him to the setting area in the master bedroom. I turned on the bedside table lamp and turned on the cameras. It was only thirty seconds before the red light came on telling me Frank was watching from his computer in Huston.

I asked him "What would you like tonight to end up being James? Do you think you will want to spend the night or just get it out of your system and go home?"

"Can I tell you in a little while," he said as he walked up to me and pushed the dress off my shoulders and it fell and hung on my rock-hard nipples. Then he pulled slipped it off the nipples and let it fall and flutter to the floor.

He just stood and stared at my tits with the nipples that were standing out. I took his right hand and closed it around my left tit. I used my hand to show him how to squeeze it and pinch the nipple. He raised his other hand and did the same thing to the other one. I took a hold of his hands and led him over to the full-length mirror. I stood in front of it and had him stand behind me and placed his hands back on my tits so he could watch what he was doing in the mirror. Then I let my head fall back on his shoulder and kissed his neck and ear.

"MM-MM you are doing a very good job but you can pinch the nipples just a little bit harder if you like. I will let you know if you get too rough OK."

He had a big smile on his face as he watched himself play with my tits and watched the nipples grow in his fingers. I moved his right hand down over my stomach and then down to my panties. He rubbed all around my camel toe and then slipped his middle finger pushing my panties into my wet pussy.

I told him in a low sensual voice, "You are about to make a woman cum for the first time in your life. Now put your hand inside the panties and I'll show you how to rub my clit so I can so you can give me an orgasm OK."

He put his hand inside my panties and I guided his index finger down through my dripping wet slit then brought it back up to my clit and had him run it in small circles around it. I was moaning into his ear.

He asked "Am I doing it right? It feels wet and warm down there."

"You are doing just fine, do you like how it feels?"

"Yes, I have never felt something so wet and warm," he said in a labored voice.

"That means you are doing a really good job!"

"You are pleasing a woman and I think you like it," I said as I reached back and played with his hard cock.

I took his hand and moved my panties to the side and pushed two of my fingers inside my wanton pussy and then pulled them out and brought them up to his mouth.

Then I said "Open your mouth." he did and I pushed them in and he sucked the juices off of my fingers.

"MMM, I like that," he said as he reached down and pulled the strings on my panties and let them fall and they were dangling between my thighs. Then he pushed my legs apart and they fell to the floor. He looked at my bald pussy in the mirror and then pulled the lip apart and ran a finger through my red-hot snatch. That's when he gently rubbed my clit until my knees buckled and I started to fall, he cough me and walked me over to the bed. I sat on the corner of the bed with one leg on the side and the other on the end.

I reached up and took off his jacket and shirt and ran my hands over his muscular chest it had just the right amount of well-groomed hair. He was looking me in the eyes as I unbuckled his pants and found a couple of surprises, first, he was commando, and second, was his rather large, shaved cock that popped up in front of my face. I reached out and took a hold of it and licked it up and down then I had him step out of his pants. His dick was right in my face and I sucked his balls into my mouth. He moaned and held my head where it was. I alternated between each of his balls and then licked up his long up turned shaft.

I looked up and asked like a shy little girl, "Can I suck your big love stick?"

He said "Please do. So far this is the best blow job I have ever had. Please don't stop. Show me what I have been missing all my life!"

Then he said, "But let me know if I should pull out when I get ready to cum?"

I took him down my throat until my nose was hitting his pelvic bone. I stayed down for as long as I could, then came up slowly. I kept eye contact the whole time and the look on his face was priceless. When he opened his eyes and saw me watching him he, put his hands on the side of my face and made tender love to my throat.

I could feel he was not long for my mouth so I took over the blow job and bobbed up and down turning my head to give him that friction that I wanted, and he needed, and probably never had gotten. I knew his boyfriend had never done that for him. I wanted it to be the best blow job of his life. I could feel his ball start to contract and he was trying to pull out but I pulled his ass back so he would finish in my mouth. His whole body shook as he was cumming.

"Oh shit, Oh shit, I cumming, Oh God."

When he was done I stood up and kissed him while I still had his load of cum in my mouth and we shared it. It was the kind of kiss that I use to remember getting from a first-time boyfriend after his first blow job because he wanted more of them in the future.

He had sweat rolling off his body so I took him to the master bath and we showered in silence. We dried each other and I brought him back to the bedroom and he started to get dressed, while I was getting us water from the kitchen.

I stopped him and said, "Unless you have someplace you have to be, or you did not like that I just did, stop what you are doing and get in bed."

He said, "I thought that with you girls it was one and done."

"No sweetheart it's time for you to return the favor and then, I want you to feel what it is like to fuck your first female pussy."

He put his pants back on the chair and sat down on the bed next to me. We continued kissing and his hands wandered all around my body. He had the instinct to know what to do. He had me all worked up in no time. He started kissing down my neck and had me squirming and then he took a nipple in his mouth and started sucking it. I was leaking juices out of my pussy that ran down onto my ass. His hand worked its way down between my legs and started rubbing my pussy which was driving me crazy. I started bucking as his finger made me orgasm again. I could feel the cum flowing over his fingers.