Sharing Jill Ch. 05

This is a series I have been writing for a follower with a shy, petite, Asian-American wife who would love to see her sleep with other men. I have written the other chapters from his point of view in the first person. In this chapter, I am going to start in the first person, switch to third person to be better able to describe events as they happen, then end in the first person again.

***

My wife, Jill, has come a long way from her shy, self-conscious ways to being more open about sleeping with other men and showing off her lovely, petite body. I'm actually shocked by how far she has progressed and her openness to sleeping with another man or men has made her even more desirable to me. Seeing another man's cock in her mouth or seeing her writhing in pleasure as her pussy gets pounded, simply drives me wild. I especially love sliding my dick into her sloppy pussy after one or more men have been there before me. I can't explain it, even though I have tried to understand my inner most deviant desires.

Jill seems to only want to experiment with other partners after lengthy breaks in between our adventures. I think she is torn by her inner desires and the effects of her conservative, Asian-American upbringing, which makes her feel guilty for enjoying her episodes of being a full-blown slut. I fully understand and realize she has to be the one to say when she is ready for another sexcapade. Heck, if it were left to me, I'd probably have her have sex with someone else several times a month but I know that will never happen.

We also have other portions of our lives to lead which include work, family and being a couple in our own right with dinners, vacations and enjoying our marriage. But there are times when the opportunity is right and she is feeling a little frisky so we break out of our routine lives. I think that may be the driving force for both of us; the fact that our routines sometimes take over our lives and our sexual adventures are a way of breaking free and doing something adventurous and downright naughty shatters the ordinary part of our lives. It has a way of making us feel alive.

Jill and I are like every other couple you see walking down the street, while out to dinner or out shopping. You would never suspect that she has slept with several different men, sometimes several at once, with my full approval and while I watch. We appear to lead very normal lives, which, most of the time, is true. Sometimes I play a little game when I see an anonymous couple. I wonder what their sexual kinks are and what they might do behind closed doors. I wonder if they do things like Jill and I.

After her gang bang with Rob, Frank, Johnathan and myself, Jill wanted to take a step back from our sexual explorations. She was concerned that things were getting out of hand but, deep down, I think she was a little afraid of how much she enjoyed herself and needed to sort things out in her own mind. This was really going against her normal, conservative behavior and I knew I had to let her figure it out. I was a little scared that I may have pushed her too far by having her fuck three other guys that night, even though she invited one of them and may have ruined the chance for a repeat performance.

We were a little busy in our professional lives anyway. School had started again and she was busy with classes. She was doing some research in her field in order to try and move up the ladder at her college too, so it left little time for fun. I got busy at work so our careers left little time for play.

Jill came home one day and told me she had an opportunity to go to a two day conference that would help her in her research project and she had already confirmed her attendance. I would never stand in the way of her advancing her career; it's not like she needed my approval anyway. It did get my perverted mind working though. I kept picturing Jill meeting someone at the conference and having sex with him. In my mind, I found the idea exciting but, on the other hand, I always enjoyed watching other men fucking my wife and I didn't know if I could handle not being there. Being with Jill while she was with other men also allowed me to "protect" her so things didn't get out of hand with someone wanting her to do something she wasn't comfortable doing.

It would be weeks before she would be going to the conference so it gave me plenty of time to fantasize and deal with my feelings. I didn't want to suggest something to Jill if I weren't fully prepared to let her follow through. I have to tell you, the more I thought about Jill being alone with another man, the more I liked the idea. Of course, I would have to hear all the juicy details afterwards though. Not knowing what happened would kill me, besides, that was the exciting part of allowing my wife to sleep with another man. I kept my thoughts to myself for a couple of weeks and brought up the idea one evening while having dinner on our back patio.

"Your conference is in a couple of weeks Jill and I was thinking."

Jill laughingly responded, "Oh no, I have a feeling I'm about to hear about another perverted idea of yours Kevin."

I could only smile, at first. She knew me too well.

"You know, you'll be alone out of town and if the opportunity should arise, I wouldn't mind if you, you know, slept with another guy."

"I knew it. I don't know Kevin. I've only done these things with your encouragement and I know how much you like being there. Besides, this is strictly a business trip."

"You'll have time at night to socialize. I'm just saying, I'd be okay if you found a playmate."

She playfully told me, "It's not going to happen, so get control of your perverted mind."

I decided to drop the subject that evening but I brought it up a few more times before the conference. At times, I would tell her of my fantasy while we were making love. She would meet someone at the bar, he'd flirt with her and they would end up in his room and then tell me all about it when she got back to her room. Jill would tell me to stop talking about it but I could tell she was turned on by the fantasy. I wasn't confident that she would actually go through with it, although it was fun to imagine her getting picked up in a bar without me.

The night before she was to leave, I tried to get her to pack some sexy clothing but she reinforced the fact that this was a business trip where she would be with other professionals in her field, hoping to make some connections and wasn't going to dress like a slut. I was disappointed but fully understood.

The next afternoon, I drove her to the airport, kissed her goodbye and told her to, "Have a good time," with a wicked smile on my face along with a knowing wink. She gently slapped my shoulder and called me a "pervert" again before she went to catch her plane.

**********

The conference didn't start until the following day so Jill had that evening to herself. She was wearing a pair of black leggings and a soft pink, body hugging, long sleeve top and decided to check out the nearby shopping district. Every time she would go into the changing room, Jill would take a couple of pictures in various stages of undress and send them to Kevin in order to tease him while she was away. She would send him some photos with her in her bra and panties, or topless or some of her totally naked. Kevin's favorite ones were when she would try on lingerie and send him the pictures. She had no idea that when she would do this that he would sometimes show them to their older neighbor, Frank. She tried on several dresses and decided to buy a short, cute little sundress and couple of souvenirs before heading back to her room.

After relaxing and freshening up, Jill decided to head to the sports bar next to the hotel for a quick dinner. It was uncomfortable for her to be eating out in public by herself but she made the best of the situation. She was really looking forward to the conference so having a meal by herself wasn't a bad price to pay for the experience she would be gaining. Over dinner, she noticed an older gentleman also sitting by himself who kept looking her way and giving her a casual smile. Jill smiled in return but looked away, not wanting to encourage him. She smiled and thought Kevin would be so disappointed in her.

When she finished her dinner, Jill decided to have a glass of wine at the hotel bar before turning in early to get some rest for what promised to be a full schedule of seminars the following day. She also ordered a glass of water so the alcohol wouldn't affect her so quickly. Being a petite woman, she couldn't tolerate a lot of alcohol. She struck up a casual conversation with one of the bartenders and didn't notice that the gentleman from the restaurant was now sitting a couple of stools away from her.

When she finally did notice him, he inquired, "Are you here for the conference?"

Jill answered that she was and he replied, "So am I. My name is Jason."

Jason looked like he was in his early to mid-50's with salt and pepper hair, trim and handsome. He had a distinguished look about him. He struck up a casual conversation with Jill and even moved closer, into the stool beside her. They continued to talk about the conference and what they hoped to learn from it. They talked about the courses they taught at their colleges and realized they had a lot in common.

While Jason wasn't necessarily looking to hook up with anyone over the next few days, he couldn't help but be drawn to Jill's beauty, her slender, petite frame and the fact that she was by herself. He, too, was alone and he was, at minimum, looking for a social connection. He noticed her wedding ring but that didn't mean they couldn't be professional acquaintances.

Jill could see Jason's eyes glancing down to her breasts at times and didn't understand why, as she had small breasts. It wasn't until she excused herself to use the restroom that she understood why. The hotel air conditioning kept the room chilly and when Jill looked at herself in the restroom mirror, she could see that her nipples were poking out from underneath her tight shirt. With her smallish breasts, she often wore only a simple lace bra. She was a little embarrassed but also liked the fact that she drew the attention of an attractive older man.

Jill returned to the bar and after she finished her wine, Jason offered to buy her another but she gratefully declined, telling him she was tired and wanted to turn in early. Jason looked disappointed but said he understood. She took another sip of her water and accidently spilled some down the front of her blouse, further exposing her hard nipples. Jason couldn't help but stare as Jill tried to dry herself with a napkin. She even blushed a little.

After giving Jason and a few guests a little accidental show, Jill excused herself and got up to leave. She wasn't going to stay in the bar with a wet shirt. Jason said he would look for her the next day. Jill could feel his eyes watching her walk away from the bar. He liked her small frame and loved her tight little ass in her black, form fitting leggings. Jill felt herself getting aroused after realizing Jason was trying to pick her up at the bar and from her wet shirt exposure.

When she got to her room she sent a picture of herself in her wet shirt to Kevin knowing he would get a thrill out of her accidently exposing her breasts in a bar. He appreciated the photos but his wife told him there was more that happened. She went on to tell him about Jason, how he struck up a conversation with her and how she spilled water on herself. Her husband was disappointed that it didn't go further.

Jill told Kevin, "Don't get your hopes up dear. I doubt anything is going to happen while I'm here."

In the typical mind of a man, Kevin thought, "At least she didn't say nothing would happen." There was still a chance. A very slim chance but there was a chance she would do something.

That didn't stop Kevin from trying to convince his wife to sleep with someone while at the conference. He began to tell Jill how Jason was probably jerking off right now thinking about her and fantasizing about fucking her. She told him to stop but he could tell she was getting aroused and continued to encourage her to explore her sexuality.

Kevin told Jill how he had an erection just thinking about the possibilities and started a video chat. Jill ended up doing a strip tease while Kevin told her to pretend Jason was in the room with her. They ended up having phone sex while they each masturbated to the thought of Jill having sex with another man while away from home. He told her in explicit detail what he thought Jason was thinking as he saw her alone in the restaurant and then again in the bar. He would be distracted by her nipples poking out of her shirt and his lust would build when she spilled the water on her blouse, briefly exposing her areola to him. He told her how wonderful she looked in her black leggings and how he noticed guys checking her out when she wore them. The more he talked, the more Jill got turned on and rubbed her clit. They both came within seconds of each other.

They ended their video chat with expressions of love for each other and Kevin telling Jill, "It would be so hot if you fucked him Jill. I just want to hear every last detail."

Jill responded, "Don't get your hopes up dear. I love you. Good night."

Jill couldn't help but let her mind think of the possibility of having sex with another man while away from Kevin. Her husband had planted the seed in her mind and the fantasy was taking root as she drifted off to sleep.

The next day, Jill was focused on the conference and determining what sessions she would attend. It was an opportunity to meet new people, make some professional connections and learn from experts in her field that may help her in her research. While she dressed in business attire, her skirt was still form fitting, falling to just above her knee. When she sat down it would ride up and show off some of her firm legs.

When she walked into the first session, she noticed that Jason was also there and he immediately waved her over to an empty seat next to him. She blushed a little when she first saw him because her mind immediately went back to the phone sex she had with Kevin and the fantasy of having sex with her new found friend. They ended up being together in four of six sessions the first day and even sat at the same table during lunch. They got to know each other a little better in small tidbits during the course of the day.

It turns out Jason was divorced and wasn't dating much. He found it difficult to get back into the dating scene after having been married for over 25 years. He felt too many women his age were trying to find another husband and he didn't want to get into a serious relationship with anyone. She told him how Kevin was her high school boyfriend and had broken up briefly before getting married. Jason and Jill were slowly developing a bond.

After the last session, Jason asked if Jill wanted to join him for dinner and she readily accepted. She didn't like eating alone and Jason said he ate too many meals by himself and would enjoy the company of a young, intelligent, attractive woman. They decided to go to their respective rooms to relax and meet in the hotel lobby at 6 PM.

Jill went back to her room and sent Kevin a text message about her plans to have dinner with Jason and his response, predictably, was to, "Go for it. He clearly finds you attractive. I promise I won't be jealous."

Jill responded, "It's not going to happen so forget about it. We are just friends."

His message read, "Wear something sexy just in case."

Kevin was disappointed but still held out hope that things would change later. Jill just shook her head and smiled at Kevin's last message. He never gave up. He had a one track mind. She still had to decide what to wear but her options were limited. She had a long sleeve, off white blouse and a form fitting, black skirt. She remembered that Kevin had slipped some sexy underwear into her suitcase and decided to be a little adventurous underneath her conservative outer clothing. She put on a lace bra and matching bikini panties and checked herself out in the mirror. Her bra could be seen through the contrasting color of her blouse but wasn't real obvious.

After putting on a pair of low, black ankle strap heels, Jill gave herself the once over in the mirror and left to meet Jason in the lobby. Jason saw Jill as soon as she got off the elevator and couldn't take his eyes off of her as she walked up to him.

"You look lovely tonight Jill."

"Thank you Jason. Where do you want to go?"

"There's a steak and seafood place down the street. It will be my treat."

"You don't have to do that, I have an expense allowance."

"No Jill, I insist."

Over dinner they talked about their personal lives, work and their professional goals. Jason had a witty sense of humor and made Jill laugh. There was a connection being made. When there was a lull in the conversation, they looked deeply into each other's eyes. Jill felt awkward in the silence and stares but, at the same time, she was turned on by the mixture of his charm, intelligence and wit. In her mind, she was wondering what it would be like to have sex with him but she was too shy to be bold enough to pursue that option. Jason could feel the special connection that was happening between him and Jill. He was entranced by her intelligence, dark eyes, petite frame, lovely smile and her awkward shyness.

Jason looked directly into Jill's eyes and told her, "Your husband is one lucky man. You're smart, beautiful and if you don't mind me saying, you're sexy too."

Jill blushed at his compliments and replied with a simple, "Thank you." She was uncomfortable receiving such compliments and went on, "I don't think I'm that sexy at all Jason."

"Don't be silly Jill. If you weren't married, well, I'd pursue you myself."

Jill remembered Kevin had encouraged her to experiment while at the conference and without thinking, she replied, "Well, my husband isn't here."

She immediately regretted telling him that. It was so out of character for her. She felt doubly regretful by the shocked look on Jason's face. Maybe he was just being nice when he said she was sexy. He hadn't dated much since his divorce and was awkward around women after not having dated for so long. He never expected Jill to be open to the possibility of a sexual relationship with him. It was almost like she was calling his bluff, he didn't quite know how to respond but he also couldn't pass up an opportunity to be with such an attractive, younger woman.

Jason responded, "I won't tell him if you don't. We could continue our conversation in my room if you like."

Jill's heart was racing. She couldn't believe where this conversation was leading. She felt like she was cheating on Kevin but he also encouraged her to explore the sexual possibilities while away. She'd slept with several other men so it wasn't like she'd never done something slutty before.

After a short pause, she replied, "I'd like that. I'd like that a lot."

Jason, stunned by his surprise stroke of luck, quickly called for the waiter to bring the check while Jill excused herself to go to the ladies room where she placed a quick call to her husband.

After quick greetings, Jill told him, "It's going to happen."

"What's going to happen?" Kevin had convinced himself Jill would never stray on her own so he was confused.

"I'm going to sleep with Jason but I wanted to make sure you were still okay with it first."

Kevin sounded like a kid getting a special birthday present. "Are you kidding? I'm more than okay with it. Damn honey, I'm getting hard already thinking about it. I can't wait to hear all about it later."