Sharing Jill Ch. 02

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This is the 2nd chapter of a shy wife who becomes a hot wife.
12.3k words
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Part 2 of the 5 part series

Updated 06/09/2023
Created 08/31/2018
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Jay142
Jay142
3,634 Followers

After our evening with Frank, Jill went into a bit of a shell. She was a little embarrassed by fucking our neighbor even though we all seemed to have enjoyed it. She can't hold her liquor and she was a little drunk but I was hoping she would want to have more experiences with Frank or other men in the future. We talked the next morning and she admitted that it was fun to do something so kinky but was worried that Frank would want to sleep with her on a regular basis. While that wouldn't have bothered me, Jill wanted me to let him know that it probably wouldn't happen again. I was disappointed but I had such a good time, I knew I would try to get her to do it again with Frank or another man at some point in the future. I just had to bide my time, just like the first time.

Jill did gain more confidence in herself after our encounter with our neighbor. I think she finally realized how sexy she was. Even though she was a petite, a barely five foot, Asian-American with 32a breasts, a lot of guys would check her out. She was a beautiful woman with long, dark hair and slender body. I think a lot of women think that all men are interested in big breasted women but that simply isn't the case. 90% of being sexy is believing you are sexy and Jill was starting to believe.

She began to dress less conservatively with shorter dresses and skirts, tighter and smaller shorts and would go without her bra more often. She was no longer embarrassed when her nipples would stand out from underneath her shirt and even noticed more guys looking at her breasts. Jill even got more adventurous by wearing tops that would show just a hint of her areola through the haze of the material. While I couldn't talk her into fucking another man again, I was enjoying her new found exhibitionist side.

When we were out in public, my wife wasn't as concerned about keeping her legs together while wearing a short skirt. She began to enjoy letting strangers peek up her skirt or leaning forward to let them see her bare breasts down her blouse. One time we were at the mall and Jill was wearing a short sundress that didn't reveal much until the light hit the dress just right. That is when you were able to see right through the dress and you could see her tight, little ass in her thong underwear. One young man practically stalked us through the mall, catching occasional glimpses of my nearly naked wife through her transparent dress.

Jill saw him follow us on to the escalator but was several steps below us. She then bent at the waist to look into her packages for a receipt but was really giving her young voyeur a nice, long look at her bare ass. She swore she didn't know he was following us but she was super horny by the time we got home. I told her about all of the guys I saw looking at her while I fucked her, knowing each of those guys wished he was with her instead of me at that moment.

One time, I talked Jill into teasing the pizza delivery guy. She pretended she just got out of the shower, her body and hair dripping wet and had a towel wrapped around her that barely covered her ass. When my wife opened the door, the look on the delivery guy's face was priceless. He was about 20 years old and he just stared at Jill, barely able to talk. Jill explained that he arrived sooner than expected and apologized. She took the pizza and bent over to place it on a coffee table, then opened the box to make sure it was the right order. The whole time, she was exposing her ass to the young delivery guy. He watched intently as she looked for her purse then, as she was fumbling for the money, the towel "accidently" fell to the floor. Jill stood before him completely naked. His mouth hung open as he leered at my wife's small breasts and dark nipples. His eyes quickly focused on her neatly trimmed pussy with her dark landing strip of pussy hair. She picked up the towel but never covered up as she paid him. He had a big grin on his face as he stepped outside and took one more look at my naked wife before she closed the door.

Jill let out a sigh of relief and said, "I can't believe I just did that. Did you see the look on his face?"

"You were amazing dear. That was awesome."

We both laughed a little and talked about how he would be telling his co-workers and joking that we will get the fastest pizza delivery in the area after that. Our pizza got cold as we rushed to the bedroom to celebrate Jill's latest adventure. I loved the new, confident Jill.

As Jill sucked my dick, I told her, "The delivery guy would love to have gotten a blowjob from you. He'll be jerking off tonight imagining you on your knees like this."

While I was fucking her I said, "Pretend he's fucking you right now. I bet this is what he was hoping to do to you. He'll never forget that delivery thanks to you." We had a great time reliving Jill's risqué behavior many more times since.

About a week later, Jill was telling me about a grad student she had in one of her classes. He was a good looking, former athlete who came from a wealthy family. He seemed to think he could get through life on his good looks, charm and money. Rob was constantly trying to charm her into giving him a better grade but she would have none of it. No matter how many times he complimented her or told her she was the best professor he ever had, she demanded that he do the work needed to get past her class. He would get frustrated by his "C" grades but didn't seem to get the message of doing the readings, research and effort needed to improve. Despite this fact, Jill thought he was handsome and had a great body.

Throughout the spring semester, my wife would tell me how frustrated she would get with him because he was an intelligent man but simply needed the self-discipline to further his studies. He would set up meetings with her trying to talk his way to a better grade. About halfway through the semester, I noticed that every time Jill told me she had met with Rob, that she wore a shorter skirt or body hugging dress but I didn't think too much of it, after all, she was loosening up in her manner of dress anyway.

At the end of the semester Jill came home and told me that Rob had asked her to be his advisor on his Master's thesis project which meant that she would be meeting with him throughout the summer until he submitted it in mid-August. I asked her why she would agree to help him, seeing it seemed she didn't really care for him that much. She told me that he wanted someone who was more critical of his work and he thought he learned more from her classes than the others. When he told her that, she found it difficult to say "no." She would meet with him during the last couple weeks of the semester but it would require her to meet with him periodically during the summer. I knew this was part of her job so it wasn't out of the ordinary but it sounded like he charmed her into being her advisor and she fell for it.

I continued to take note of how she dressed when she was meeting with Rob. One time, she wore a short yellow sundress that she would normally wear a slip underneath but on that day I noticed she didn't wear one. I noticed because when she bent over or if the light hit the dress just right, I could see through it. Her petite silhouette was so sexy and I noticed she was wearing a white lace thong underneath. She took more time making sure her hair was done to perfection and added a little more makeup than she normally wears. My first instinct was to warn her that I could see her panties but I devilishly decided not to. It turned me on to think that others, especially Rob, would notice her attire. If she was dressing this way to get Rob's attention, that was even better, but I doubted Jill would do that intentionally without my encouragement.

When Jill got home that evening, she told me that she was again frustrated with Rob because they had a disagreement over the focus and direction of his thesis. She was calling him arrogant and stubborn but at the end of the meeting, they finally came to an agreement after a long debate. I gave her a quick hug and kiss to try and calm her down and I noticed she was wearing perfume, something she never does at school.

During our dinner conversation, Jill informed me that she had one more meeting with Rob at school just before exams but after that she agreed to meet him here at our house because he didn't live too far from us and it was more convenient for both of them. I didn't think anything of it and I was curious to meet this young man. While there was a part of my wife that was put off by his arrogance, there also seemed to be a part of her that really liked him. She did mention that he was handsome and had a great body and I wondered if she had a slight crush on him too.

On the day of her last meeting at school with Rob, Jill wore a tight, black, body hugging, mini skirt and sheer white blouse that clearly showed her white lace bra underneath. When she sat down her skirt rode up to her mid-thigh and, it was almost impossible not to see her little pink panties underneath. She also wore a pair of 3" high heels, which she hardly ever wears to school. I made sure to note that she wasn't wearing perfume when she left that day but had some on when she came home.

My mind was going wild picturing Jill moving around her office as Rob watched her every move, taking in her lovely, slender legs and trying to see her nipples through her sheer blouse and lace bra. I imagined my wife, crossing and uncrossing her legs in front of him, letting him see her pink panties up her skirt. I thought about him undressing her with his eyes wishing he could bend her over her desk to fuck her or get her down on her knees to blow him. I told myself this was probably just my perverted mind working overtime, that my conservative wife would never act like this without strong encouragement from me and even then, she would only reluctantly agree. A man can always dream about it though.

A few weeks later, Jill told me that Rob would be stopping by that evening to meet with her but it probably wouldn't take that long. She was wearing a tank top, with a bra and tight running shorts. I loved seeing her in these shorts because they showed off her legs and ass. Secretly, I hoped Rob would like them as much as I did. When the doorbell rang, I answered the door to greet Rob who was around 25 years old, about 6'4, 210 lbs., broad shoulders and deep blue eyes. My wife said he was athletic and handsome but that was an understatement.

I said, "You must be Rob, come on in. Jill has told me a lot about you."

"I hope she wasn't too harsh in her description." He laughed a little.

"Oh no, she told me what a great guy you are."

Jill then came into the room and Rob's eyes immediately scanned her body from head to toe and back again. They both smiled broadly as she invited him in. It was a nice night and they decided to meet outside on the deck. I sat in the living room reading but I could see them through the patio door. I noticed how Rob would look deep into Jill's eyes when they talked and how his eyes roamed to check out her legs when she wasn't looking. I swear he was trying to peek down her top too, not that it bothered me at all.

When they were done, and just when Rob was about to leave, I asked him if he wanted a beer. Jill looked at me like she wanted me to shut up. Every married guy knows that look but it was too late, he quickly agreed to one beer. Jill feigned a smile and went to get a couple of beers for us and a soft drink for herself. As she walked away, I noticed Rob staring at her ass. I think he had a little crush on his professor too. I told him that Jill doesn't drink too much because it goes right to her head but will on special occasions.

We sat around the living room chatting while we sipped our beers. It turns out Rob was a quarterback in high school and got a full scholarship to a local university. Now that his football playing days were over it was time to focus on his career. He appreciated Jill advising him and he openly admitted he can be stubborn at times and knew he frustrated her at times.

Jill tried to laugh it off, "You aren't that bad Rob."

"Come on Jill, I know there are times you want to hit me with something but I'm trying to listen more."

When Jill left the room to get more drinks, I asked, "Rob, I bet being a quarterback, you must have had to fight the girls off at times."

He was reluctant to say too much but replied, "I had my fair share of fun. There were some benefits that came with being on the team."

I was sitting next to Rob on the sofa and when Jill returned with our beers, she leaned over to pour them. We both got a clear view down her top to her lace bra. Her brown nipples could be seen through the lace. I noticed out of the corner of my eye that Rob was clearly enjoying the view. My dick started to stir in my pants as my deviant mind went to work.

We continued our small talk and Rob left after he finished his beer. Jill was a little frisky and let me know that we should go into the bedroom. Never one to turn down an opportunity for sex with my wife, I quickly followed her.

While we were making out, I told Jill, "I think Rob as a little crush on you."

"Stop it, no he doesn't. He's had plenty of women so I'm sure he doesn't even notice me."

"I think you're wrong dear. He was watching every move you made tonight. I think he really liked your shorts."

She told me to "Sshhh."

I didn't want to push it too far so I didn't say anything further. My mind began to imagine Rob being there as Jill slowly stripped off her clothes and him enjoying her naked body as much as I was. While I was licking and sucking on her clit, I was imagining what Rob would be thinking if he had the opportunity to do the same. While my wife sucked my dick, I couldn't help but to wonder what his looked like and how great it would be to see her lips wrapped around it.

As I spread my wife's legs to enter her, I wanted to watch some day as Rob did the same. While I was fucking her, I leaned in to whisper in her ear, "I bet Rob would like to be fucking you right now."

She moaned softly in response and said, "He has no interest in me. It's just your perverted mind at work again."

I bent her over and started to fuck her hard, "I think you are wrong dear. I think Rob would love to have you bent over fucking your tight little pussy."

She started to cum and I quickly followed, spraying my sperm into her juicy pussy thinking of how I'd love to see her prize student filling her pussy with his dick and cum.

It was a couple of more weeks before Rob met with Jill again. This time it was a scorching hot, 90 degree evening. Jill was dressed in a tank top again but I noticed she didn't have on a bra and her shorts showed a bit of her ass cheeks. She clearly didn't mind if Rob saw her like this. When Rob saw her, his eyes again scanned her petite body and focused on her hard nipples poking through her top, the air conditioning causing them to harden. I didn't say anything but I was going to pay real close attention to how they interacted with each other. Jill got a big smile on her face when she saw her student, like a schoolgirl smitten with the star football player. They clearly had a crush on each other and I wondered how I could stoke the flames.

They sat around the small kitchen table discussing the thesis but I noticed them looking deep into each other's eyes at times. There were times when he would say something and Jill would giggle like a nervous teenage girl. I watched that every time Jill looked down at the notes on the table, that Rob took the opportunity to look at my wife's small tits. She even leaned over a couple of times to point out something on the papers in front of them but he was only focused on trying to look down her top at her bare breasts. I thought that Jill must have known what she was doing but, on the other hand, she is still so naive I wasn't 100% sure.

When they were done, I again invited him to stick around for a drink. Jill shot me that "look" again but couldn't openly object. He stared at my wife's ass as she fumbled around in the fridge for a couple of beers. He must have felt me watching him check out my wife because he looked up at me and looked nervous at being caught.

Of course, I didn't say anything but thought, "If he only knew how much I wanted him to stare at her and more."

As we were drinking, I mentioned, "This is a great night to take a dip in the pool. Too bad you don't have a swimsuit Rob."

"I would love to go into the pool but I'd have to swim in my underwear."

Jill was shooting me more looks but that didn't stop me. "I don't think that would be a problem. You'd be underwater most of the time."

He looked up at Jill, "I think that's up to your wife. I don't want to make anyone feel uncomfortable."

"Don't be silly, it will be fine, wouldn't it Jill?"

Jill began to stammer, "I, um, I guess so." She shot me another look when Rob looked at me.

"Great. We'll change and be right back."

When we got into the bedroom, Jill was frantic, "What do you think you are doing?"

"Oh, don't worry dear. It will be fine. It's so hot out, I was just trying to be friendly."

She reluctantly changed into her bikini at my urging but put a beach cover-up over it before we took Rob out to the pool with a couple of more beers. I was the first one in the pool and told them how refreshing it felt. Rob then stood up and took off his shirt revealing a nicely chiseled body. He had muscular shoulders and arms, a broad chest and six pack abs. Heck, even I thought he was gorgeous. He then slipped off his shorts, leaving only his navy boxer/jocks on which clung tightly to his muscular ass. He could have been a model. He quickly dove into the pool.

We swam around for a minute before we both told Jill to join us. She needed a little encouragement before she finally peeled off her cover-up. Rob and I were watching as she revealed her bikini clad body. I could tell he was enjoying seeing her this way. We swam around for a while before Rob said he had to leave. He was the first one out of the pool and I noticed Jill staring at his wet body and how his wet underwear clung to him. It was tough to tell in the dark but it looked like he had quite the package, if you know what I mean.

He wrapped a towel around himself as Jill and I got out of the pool to see our guest out. Jill's bikini bottom rode up into the crack of her ass but she never straightened it out which wasn't normal for her. Rob watched closely as she bent over to put on her sandals and began to dry herself off. There is no way she couldn't have known he was looking at her every move. She even made sure she walked in front of us on the way into the house. In the light of the living room, Jill was able to get a good look at Rob's young, muscular body. He was able to check her out too. He made no effort to hide the fact that his eyes were roaming from the top of Jill's body to the bottom. She seemed to enjoy his stares, standing proudly before him.

When he went to the bathroom to change back into his shorts, I said to Jill, "My goodness, he has the body of a male model."

Her response was, "Oh, really, I hadn't noticed."

"I call bullshit." But she wouldn't admit to liking his young, muscular body.

However, when he left, she was all over me wanting to have sex again. She took me into the bedroom and quickly stripped off my bathing suit, got down on her knees and started to give me a blow job. She sucked my dick furiously for a few minutes before pushing me onto the bed, stripping off her suit and climbing on top of me. She was hot as a firecracker. I played with her tits as she bounced on my hard cock.

I took a chance and asked her, "You want to fuck Rob, don't you?"

"Don't be silly, I can't do that. He's my student."

Jay142
Jay142
3,634 Followers