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Jill - Dipping Our Toes - The Next Few Weeks

Jill and I take the next significant step

The next few weeks...

After we got home, things as they are wont to do, went back to normal. Our sex life did improve and we were able to talk more openly about our relationship and what happened. However, we were not out looking for someone for Jill to have sex with. It was more pillow talk and our mystery man played a part in some of the role play or fantasies we would talk about.

I really tried to justify why I was so turned on at the thought of my wife flirting with and getting groped by another man.... and more that she was turned on by it.

I came up with this analogy and maybe it fits within the Hotwife community, but it works for me. Jealousy is a huge part of the equation. I love my wife dearly and do I want her to run off with someone else? No. Do I think that would happen? No. So, if I feel safe in that regard, the jealousy became a catalyst for the quickened heartbeat and punch in the gut emotion that I felt when Jill was relating her story to me. So, if Jealously were a ride, it would be a roller coaster. The first hill down is dizzying, thrilling, it feels dangerous... out of control. This woman who you love, your partner in life, feels like you have lost any semblance of control. I certainly don't mean a man should have control over a woman or vice versa.

Those who are married will understand that you have a partnership. If someone wants to buy a boat they don't just go off and buy a boat or a dress or a car or change cable service without at least discussing it with their partner in life. When we were both kind of dipping our toes in the water of this feeling of doing something society (at large) considers relatively taboo... it was thrilling, exciting, a little bit dangerous and out of control. You could only experience the thrill of the ride once you went uphill and fought for a good solid relationship that would give itself the room and the freedom of the dips and valleys.

Jill and I would still have to work our sex life around the kids. We still had jobs and obligations and everything that gets in the way of being constantly turned on all the time. Life just doesn't allow that to happen.

I work for a law firm and Jill had a solid job with an advertising agency.

There was one time I scheduled my in-laws to babysit for an overnight and surprised Jill with a weekend getaway down town. I booked a room at a posh hotel and had her things packed. I made sure to include the blue dress she wore to the reunion. She was so thrilled and excited I went through the effort of putting the weekend together for her.

On our way downtown, I suggested it might be fun if she wore the blue dress down to the hotel bar and I would be a stranger coming in and trying to pick her up. She was game for about anything because of how sweet I was being to plan the weekend. So, she agreed.

We checked in and I took the bags up to the room and I washed up and changed quickly and left, allowing her the time she needed to prep for our planned role play. She asked that I give her at least an hour. I thought it sounded a bit much, but what the hell. I left the hotel and walked around the city blockf. I kept looking at my watch. Time never passes as slowly as when you consistently look to see what time it was.

Finally, forty-five minutes had passed, so I thought that was long enough and I headed back to the hotel. I tried to put myself in the mind-frame of a traveling businessman, done with a meeting or convention and after a long day, only had one thing on his mind.

I walked through the hotel doors and into the bar area. The place wasn't really that crowded. There were a few businessmen there, a couple guys watching a game on a tv, some single folks; all of them either on their phones or looking at their phones. My eyes scanned the entire area for my favorite blue dress but I didn't see it. I looked again. Nope. Did I really arrive too early? Then I saw a woman with Jill's same hair color and style sitting at the bar by herself, but she was wearing a red blouse and skirt.

She turned her head when the bartender asked her a question, and yep, that was her. I hadn't packed her a red blouse. She must have sneaked it in between saying goodbye to the kids and my loading the car with the bags.

I walked over and took a seat next to her. She turned and smiled and nodded her head hello at me and then went back to looking the other way.

“Excuse me Mam, I thought you were someone else,” I said, tapping her on the arm.

“Oh, who did you think I was?” Jill replied.

“My wife, I was supposed to meet her here, but I thought she would be wearing something else.”

“Oh, do you like what I'm wearing?” She said turning and facing me.

It was a beautiful blouse with a plunging neckline. Bellow her breasts were three medium sized gold buttons. The top was soft and silky and had a sheer looking quality to it. The bottom skirt had a slit that rode up pretty high on her thigh and showed off her gorgeous legs.

“I, yes, I like it very much. Your husband is one lucky guy!” I replied.

“He's one late guy. He was supposed to meet me here fifteen minutes ago. I've had to start without him,” she said, nodding at her martini.

At first I was a bit confused. I know she told me an hour and I actually beat that time, so I figured out it was all part of the role play. She was going to be a semi-neglected wife waiting for her husband.

“His loss,” I replied. I extended my hand, “Dylan.”

She took my hand and shook it gently. “Jessica.”

“Nice to meet you,” I told her.

“You as well,” She said nonchalantly and turned back. Damn, she was going to make me work for this.

I decided to play up the jilted card and see if she would crack more on that angle.

“You know....if I were your husband, I definitely wouldn't make you wait.”

She turned back and smiled at me. “Well, aren't you charming. Cliché but charming.”

“Uhh. Ouch?”

This made her giggle.

“How long are you going to wait for him until you are officially stood up?” I asked and placed my hand on her knee.

She let it rest there for a moment, but then grabbed it and removed it from her knee.

“Sir, I appreciate the compliment of you hitting on me. But....,” she said, waving her hand with the wedding ring in front of me. “I'm a married woman.”

The bartender was standing fairly close to us, close enough to hear what was going on, I'm sure he had seen similar situations every weekend. But still, I watched his face and his ears seemed to perk up at the last sentence Jill said to me. He kind of smirked. There was no way he knew we were the one's actually married and this was all just part of a game.

“You are a stunningly beautiful married woman... whose husband doesn't know how to tell time or doesn't know how lucky he is.”

“Be that as it may, I took a vow,” she smiled.

“To honor and obey?” I asked

“To cherish and forsake all others,” Jill quipped.

Good lord. I didn't think she was going to be THIS hard to get. I thought I was going to stroll in here, give her a few compliments and off to the room we would go. I sat there thinking. She had finished her martini and lifted the empty glass to the bartender to give her another one. He nodded. I gave him two fingers indicating I would have the same.

“Okay, but doesn't part of cherishing mean not leaving your partner to wait on you this long and leave you open to folks like me?” I asked, trying to look for any kind of crack.

Jill grinned. “Maybe. But he takes care of me, he's a good father, we have a great relationship. Why would I risk all of that for a one night stand with a complete stranger?”

The bartender brought us our drinks. This was Jill's second and my first. I could tell by the flush in her face the alcohol was having an effect. I got an idea. I looked at the bartender's name tag. It said “Nick”

“Hey Nick, would you keep a woman as beautiful as this waiting?” I asked him.

Jill seemed to be surprised I was bringing a third party into our game, but she didn't say anything. Hey, she was the one keeping the wall up.

Nick shook his head. “I don't know man. I tend to keep out of situations like that. No means no.”

Damn it. Of course he's not playing the game. He's trying to look out for his clientele. I sighed.

Jill giggled. I'm sure thinking it was some sort of victory in her mind.

“I'm just saying.... don't you think she's beautiful?” I prodded him.

Nick was drying a glass and came over closer to us. “Oh, she's beautiful all right. Probably one of the prettiest ladies I've seen in here in a long time.”

Jill blushed. “Thank you,” she said, looking down at her martini.

“But, she has a wedding ring on, so she's off limits,” Nick said looking at me. Was there a threatening edge to his voice?

Jill must have heard it too. “No no. It's okay. He's not bothering me. We're just talking,” she told him.

Nick gave her and me a studied glance and seemed to be satisfied. “Okay, just let me know if you need anything,” he told her.

“I will. Thank you,” she said, smiling at him.

Grrr, why is she making this so hard? Sure, I was the one to bring in Nick. I thought he might be a wing man, but instead he became a cock blocker. I guess, not really knowing the situation, it was forgivable.

“So, how long are you going to give him?” I forged on.

“Oh, I don't know. I'm sure he will be here any second.”

I sat there thinking of what to say next. Another idea came.

“Do you want to bet on it?” I asked her.

Jill smiled, “Bet on it? Hmmm. What do you suggest we bet?” There it was! A crack.

I thought for a moment. “How about this. If your husband comes strolling in here in the next five minutes, I will buy drinks for you and him for the rest of the night. Drinks will be on me until you guys decide to leave.”

“Okay, and what would you win?” She asked, seeming intrigued.

“For every five minutes he doesn't show up, you unbutton a button on your blouse.

Jill seemed to be taken a little off guard. On the one hand, if she was really a woman who honestly thought her husband was going to come in any second and had the chance to win free drinks... would she take up a stranger on the bet? If she KNEW he was supposed to be there twenty minutes ago?

“Hmm,” Jill thought. She looked down, “I only have three buttons.”

“Well.” I smiled, “That would give you fifteen minutes to win the bet. Besides, he was supposed to be here almost a half hour ago now.”

“What happens after fifteen minutes and God forbid, he's still not here?” She asked. I could tell the wheels in her head were spinning on how to manipulate this back to her control.

“Oh, I'm sure you wouldn't need to worry about that. Your husband should definitely be here by then, right? If not, we'll jump off that bridge when we come to it, okay?” I said. almost condescendingly.

Jill sighed... thinking.... ”Make it every ten minutes.”

“Deal,” I said quickly. Because she could could make it every hour.... no one was coming through the door. Now, it was just a waiting game. I don't know if our bartender friend heard everything, but I think he did. He seemed to be a little less defensive of Jill now, instead more.... interested.

Jill just sat and looked at me now, not wanting to break character, but incredulous the tables had turned.

I just smirked and looked at my watch. This seemed to fluster her more. She drank a large sip of her second martini.

Ten minutes passed and time was up. Nick coincidentally had made his way back over to us.

“You guys need anything?” He asked.

“I think we're good.... Jessica?” I asked Jill.

“I'm good,” She replied. Then sat there and took another sip.

I cleared my throat and pointed at my watch.

Jill sighed again and finally said, “Fine fine.” With that, she unbuttoned the uppermost button on her blouse, which was still below her breasts. This caused the fabric on both sides to loosen up and expose even more of her cleavage. Underneath her blouse you could now see the sides of her bra. It was also red and I knew which one it was. This bra happened to be see-through.

Nick stood there watching as Jill unbuttoned her blouse. Jill looked up and noticed.

“Enjoying the show?” She asked.

“Hey I have to be here, it's my job to look after you. You made the bet.” He replied.

Now, I KNEW he heard what we were saying and whats more, he was curious. I'm sure he wouldn't mind getting a good look at Jill's girls either. Now, he would be on my side.

“Thank you Nick, you're a scholar and a gentleman. We must always cover our bets shouldn't we?”

Nick smiled, “Well, I do! Otherwise you're a welch. Nothing worse than someone that doesn't back up what they say.”

Time passed and people came and went from the bar. Nick was sure to help anyone that came up, but he was also sure to show up when ten more minutes had passed.

Jill seemed a little more nervous now. The Martinis were having their effect, but she knew now someone else was trying to get into the game, even though Nick had no idea the game was taking place.

She resigned herself again and unbuttoned the second button. The fabric of her blouse fell open even more, exposing more of her bra and the treasures they contained. Nick gave a very low appreciative whistle.

“I think I'm agreeing with this guy now. Your husband's an idiot,” Nick said softly.

“You have no idea,” Jill replied back and gave me the stink eye.

I couldn't help but chuckle at that. Not only did I manage to turn the tables on Jill, I now had someone to have my back.

“Listen guys. I know my husband is going to be here.... but just in case, is there a more private area we can go?” Jill asked Nick, but was looking at me.

“Sure, we have a private room around the corner. Usually it's reserved for private dinner meetings, but it's not booked, so you guys are welcome to it. Go head and go in. I'll be in in about.... ten minutes to check on you.”

I snorted.

Jill and I walked around the corner of the bar and found the door to the private dining area. It was a really small room, just big enough for a table and chairs. She and I walked in and I closed the door.

Immediately she began to slap my harm in a playful, but violent way.

“What?” I asked laughing.

“You were supposed to come pick me up.... not get other people involved!”

“I tried! You left me no openings! I can't help it you are so beautiful that your knight in shining bar towels was willing to give up his principles for a look at your ladies.”

She slapped me again.

“Jill, look, if you want to welch on the bet, we can simply walk out of here and there's no harm, no foul,” I said earnestly, giving her an easy out. I could see the wheels spinning in her head. I knew this was pushing her beyond what two martini's would normally allow for.

She thought for a while.

“I told you Dylan, the name's Jessica,” She said with conviction. Okay, we both loved "Dead Poet's Society", but it didn't change my feeling. My heart swelled with pride and love for my daring, beautiful, and strong woman. I couldn't help but lean in and kiss her on the lips. She kissed me back.

“Careful now Dylan, I'm a married woman,” she teased.

“YEAH you are!” I said, grasping her close and pressing her up against me. Her blouse was now almost completely open.

We separated and continued with our playing.

“Do you think your husband is going to be looking for you?” I asked.

“Hmph, let him look. He kept me waiting WAY too long, and I ended up giving two strangers a peak down my blouse. Now I'm here in a private room with someone who I can only hope has more honorable intentions than I give him credit for,” Jill jabbed back. Seemingly actually mad at her made-up spouse.

“Yeah, you are probably giving me too much credit,.” I said casually.

Just then there was a knock at the door. It opened and in walked Nick.

“Hey guys, just wanted to let you know I got someone to help me cover the bar, so I can get you anything you need. Just let me know.”

“Umm, thanks,” Jill replied.... knowing exactly why he wanted to be our personal attendant.

“Can you give us two more?” I asked, holding up my Martini glass.

“Sure, I'll be right back,” He said, and before he left, gave Jill a look up and down her frame.

“He's certainly turning out to be pleasant,” I commented.

“Oh shut up.”

“Jessica, come on now. No need to get salty,” I laughed.

“Yeah, yeah, I know I made the bet. I certainly don't want to be a welch.”

I came closer to her and whispered softly in her ear, “Isn't there a part of you that is excited, is enjoying the attention?”

Jill thought for a moment, “I would be lying if I said no. I'm just nervous as to where this is going. This is so beyond anything I had ever thought about before... you know.”

“The reunion?”


“We can stop any time...I want you to have fun,” I held her.

“I am having fun, it's just so weird...hey, what time is it?” She asked.
I looked at my watch. “About two minutes past the last button”

“Then what happens?”

There was a knock at the door, it opened and in walked Nick with a tray and our drinks on it. He closed the door and set the tray down on the table. He picked up each of the drinks and gave them to us.

“There you go, how are you two getting along?” He asked, I could tell his eyes quickly diverted to the last button on Jill's blouse.

“Fine, thanks,” she replied.

He waited there a moment. I didn't think he was looking for a tip yet since he'd obviously opened a tab.

“I think Nick here is also wanting to take advantage of your husbands stupidity,” I said quietly.

Jill took a sip of her drink and set it down on the table. Her face was definitely flushed, but I know it wasn't just the alcohol at this point. I felt my heart quicken as she reached for the last button. Her hands were shaking a bit, and fumbled, but eventually it unhooked and the remaining two parts of her blouse fell open. There, exposed to both Nick and I were her two beautiful breasts covered with just a thin, transparent film of material. Her nipples were rock hard and pointed out against the fabric. She let her arms fall to her side and stood there letting us look without saying anything.

Last time, she was by herself when she was exposing herself to a stranger. This time, I was there. I think there was a sort of tension in the air. She definitely wasn't being outgoing or gregarious. I think she was taking it all in. She closed her eyes for a moment. I could see a small smile run across her lips. She was getting back into the mindset of a neglected wife, left open to her two male predators.

“Well?” She asked, opening her eyes and looking at both of us. Almost defiantly.

Nick let out a low whistle again. “Damn, you look beautiful. Your husband is definitely an idiot.”

“He has his moments.” Jill replied looking me in the eye.

“I think you are the most gorgeous woman I have ever seen.” I said with complete honesty.

Jill smiled. “Thanks.”

“It's too bad your husband still isn't here.” Nick commented. I'm sure he was being sarcastic.

“Yeah, your husbands still not here” I added. “You have about five more minutes until the next ten are up.”

“Okay, then what?” Jill asked in a quaking voice.

I thought for a moment.

“Hmmm. How about if we let Nick decide what happens next? He seems to be an honorable chap.” I offered.

Nick seemed to be pleased with the compliment, but still couldn't draw his eyes off my wife's chest. She stood there, allowing his eyes to drink her up. I could tell she was getting turned on.

“Okay, fine, I'm good with that,” Jill said.

“Whatever he decides is what the bet would be, right?” I confirmed.

Jill nodded, “Yes.”

So, now, we had both relinquished control over where our little role play was heading. It was exciting and nerve wracking at the same time.

Nick thought for a moment. “Well, considering you've pretty much already lost your top....”

Jill covered her face with her hands, “Oh jeez.”

“You think she should loose her skirt?” I asked and he nodded. “That sounds fair.”

Nick turned back to the door and locked it. “Just in case,” he said. “We don't normally lock it, but I think this is a special occasion.”

“So, you guys are just going to wait there? Gawking at me until the time is up?” Jill asked.

Nick and I looked at one another and nodded at the same time. This made Jill giggle a little bit. To her credit, even though there wasn't much being said, she stood there in her transparent bra and let her audience enjoy.

Without saying a word, she let the blouse drop from her shoulders and carefully folded it and placed it on the table.

“What the hell,” she smirked, “In for a penny in for a pound, right? So, you guys can at least tell me if you like what you see, I'm basically standing here topless.”

I waited just a beat, I wanted to give Nick a chance to respond first.

“It's not often someone as beautiful as you comes and sits at the bar. It's even less often I get to listen in on any kind of wager.... and I don't normally put my clients in a compromising position, but there is something about you. I thought if you were going to play a game with this gentleman here....,” nodding to me, “The least I could do was make sure you weren't taken advantage of.”

“Ohh, so this is you being chivalrous? Just looking out for me?” Jill said, humorously indignant.

“No! I mean... of course I wanted to see more of you,” Nick stammered.

“Speaking of which," I interrupted. “Ding ding,” pointing at my watch.

Jill, resigned herself and grabbed one part of her skirt and pulled at it, it came undone and she unwrapped it and it came apart. She stood there, gently folding her skirt and placed it on top of the blouse. Her panties were a light silver color. There at the apex of the material, you could clearly see a small stain. I knew this was turning her on as well.

Jill turned to look back at us, her hands on her hips. “Well?”

I swallowed, how far was this going to go? With Nick here, it was much more than I had planned.

“Can you turn around?” Nick asked.

Jill smiled, but nodded and slowly turned her body around, revealing her nicely toned ass. The panties had ridden up a bit, but she pulled them out and smoothed them out over her plump cheeks.

Nick let out a low whistle. “Damn, your husband may be an idiot, but he is one lucky guy.”

“Yeah, he is,” I exclaimed, my heart swelled with pride looking at my wife. We were both turned on knowing I wasn't the only one looking.

“Pull your panties down about eight inches,” I told her. My blood pulsed and quickened.

She looked up at me. Was that surprise? Anger? Shock? Arousal? All of them? I could actually hear Nick swallow.

“But... It hasn't been ten minutes yet,” She said.

I looked at her and shrugged my shoulders. Was she really going to go through the pretense at this point of waiting ten minutes for a pretend husband that was never going to arrive?

She seemed to go through the same argument in her head.

With a shaking voice, she simply said...”Okay”

She closed her eyes and took a deep breath. She hooked her thumbs into the sides of her panties and waited a moment. I know her heartbeat had quickened as well. Slowly, she pulled the garment down and let it stop on her upper thighs. There, before Nick and I, stood my wife in a transparent red bra, her panties had been pushed down and her pussy was exposed. For the first time since I married my wife, another man was looking at her naked sex. She still kept it trimmed and neat. Her lips, though thin, were obviously aroused. They were like two glistening flower petals covered in dew. There was something even more erotic about seeing her panties on her thigh than if she was completely naked.

Jill lost any semblance of confidence or control as she brought her hands over her face and covered her eyes in embarrassment.

“Hands behind your back please,” I demanded. She complied and brought her hands down and interlocked them behind her back.

Nick got closer to her... tentatively stepping near to her. Now what was going to happen? Jill looked at him and then at me, almost pleading in her eyes. What was she pleading of me? To let him grope her like our stranger? To make him stop? I just waited. I wanted to see what would happen. I knew Jill well enough that if she was really uncomfortable, she would stop it.

Nick extended his hand toward her crotch. She didn't move. He took one finger and reached out and ran it along her pussy lips in one slow motion.

“Mmmph,” Jill let out a soft startled moan and bit her lip. She looked at Nick to see what he was going to do next.

He pulled it back, covered in her moisture. He brought his finger up to his nose and inhaled deeply. Then he stuck in his mouth and sucked.

He croaked out a whisper, “Delicious.”

The doorknob tried to open, but it was locked. There was a quick banging on the door. “Nick?” came a voice.

Jill made a soft scream and pulled up her panties, grabbed her blouse and threw it on, quickly buttoning the buttons.

“Hold on!” Nick yelled. I could tell he was going to ask us to wait. I know Jill wasn't going to be up for that. I knew she was going to want to take me back upstairs. I think she pushed herself as far as it was going tonight.

Jill threw on her skirt and grabbed my arm, “Come on Dylan!”

The only face more crest fallen than mine must have been Nick's.



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