First Date Jitters

Jean, her husband Bob, and her date, Dylan were all feeling a bit apprehensive. It was a momentous occasion in their lives.

Jean was outwardly calm, but inside she was excited and nervous. Excited to actually be going on a date with another man since she and Bob got married, a man she really liked. She was glad they were embarking on this new adventure, but worried Bob might suddenly get cold feet or wig out.

Dylan was also calm, but apprehensive. He wanted to make a good impression. He also hoped Jean and he clicked. Even though Jean told him not to, he worried about Bob.

Bob was being Bob, excited and scared, jealous, insecure, aroused, at times filled with doubt that Jean going out with Dylan was wise, but wanting her to go on a date. He felt extremely conflicted, especially as the time Dylan would arrive to pick up Jean grew closer.

Jean and Bob discussed how they would interact when Dylan arrived and Jean and Dylan had discussed how she wanted him to act when he arrived at their house.

Jean instructed Bob to greet Dylan like he would any other male visitor to their home, "Shake his hand. Maintain eye contact. I know you've seen him, but have you two ever met? If you haven't, introduce yourself."

She continued, "After you exchange pleasantries, wish us a good evening, and excuse yourself, but be ready to come back in case I need your services. While I'm gone, absolutely no masturbating. I've left you a list of things to do to keep you occupied."

"You're not to contact me unless it's an emergency. I'll try and contact you midway through my date to check on you. I'll keep the call short. We can talk about my date afterwards. In fact, I'll want to talk about my date afterwards. I expect you to be an active listener."

"You're aware I really like Dylan. He's a neat man. Don't ask me what we did. I'll tell you only what I'm comfortable sharing with you. Don't ask me if he and I had sex. Instead, ask me if I had a good time and want to see him again."

Her instructions to Dylan were a lot shorter, "Don't worry about Bob. Expect him to be a bit nervous. Don't be surprised if I interact with him differently than you're used to seeing wives and husbands interact. My marriage is evolving so it shouldn't be a surprise my relationship with my husband is also."

She continued, "I'm not being a bitch. In order for this to work, we both realized our roles and how we interact needed to change. We're not swingers. He's staying at home keeping the hearth going and I'm not."

Dylan said he understood. Jean had never said she and Bob were in a cuckold relationship, but it didn't take him long to conclude they were. He had done some research on cuckold marriages so he felt somewhat prepared.

He couldn't help but feel a bit smug as Jean had said yes to going out with him which meant she was saying no to Bob. He knew she liked him and he liked her.

He also knew if it felt too weird, he could pull the plug and Jean would understand.

On their first date, Jean suggested they dress casual, go to a dinner, then a movie, maybe a bar afterwards.

Dylan arrived on time. He had read men like Bob were triggered by simple things, a bouquet of flowers for the wife or holding her hand as they headed to the car.

He planned on doing both as he was all about feeding Bob's fetish. The way he saw it, the deeper he could drive Bob into submission the easier it would be to pursue a relationship with Jean.

Jean opened the door.

He took one look at her and his heart was pounding. He thought she really was beautiful. He loved her dress, a purple peasant dress with embroidery. On her feet she wore sandals.

He felt a bit tongue tied as he handed her the flowers and told her she looked really great.

She took the flowers and said he looked very handsome.

"Excuse me. Bob, Dylan is here. Come say hi."

Bob appeared, not looking too nervous Dylan thought but excited. He and Dylan shook hands exchanged pleasantries.

He remembered not to ask about their plans as Jean had reminded him, "You're not my dad and you're not my husband when I go out."

Jean handed him the flowers, said they were lovely, thanked Dylan and told Bob, "Go put these in a vase. I want to be able to see them when I'm home. And get my small purse. You know what I need in it."

"Yes Jean."

Bob left and returned a few minutes later. Jean and Dylan were chatting about their dinner plans. Both were hungry.

He handed Jean her purse. She thanked him and directed her attention to Dylan, "Shall we go?"

He smiled and said, "Yes we shall."

He purposely left the door open as he wanted Bob to see he and Jean holding hands as they walked to his car.

Jean had wondered how she would react and reminded herself to let Dylan hold her hand, neighbors be damned.

Jean and Dylan's date exceeded their expectations. In the theater, he put his arm around her while they watched the movie. They didn't go to a bar for a nightcap, but did stop and eat dessert.

She had forgotten to call Bob, but figured he would be okay. She reminded herself she had told him she would try, not that she would.

He asked her on the way to her house how she thought the date went.

She said, "I thought it went really well. You're a neat man, Dylan."

He laughed, "Thank you. I thought so too. So, do you think there will be a second date?"

She answered, "Definitely."

Feeling a bit emboldened, he asked if that meant, "Should I expect a goodnight kiss?"

"That's definitely a possibility. I would ask you inside, but it's Bob's first night."

He said he understood.

He pulled into her driveway.

"Turn off the car," she said.

He rolled down the windows as the night was warm.

She laughed, "Are you thinking we might be here for a while?"

He answered, "I'm hoping we are, even if it's just to talk."

He knew he was saying all the right things, but it wasn't an act.

"Well, are you going to kiss me?" she asked.

He put an arm over her shoulder, turned towards her. They kissed lip to lip several times.

"That was nice."

He sensed she wanted to be kissed again so he did.

This time their lips stayed in contact for at least a minute until Jean extended her tongue. They shared an intense and long French kiss.

She seemed emotionally moved by the kiss. He initiated another, this time their hands roamed freely. He massaged her breast as they made out. He thought about doing more, but wanted to not come across as too aggressive.

She broke from their kiss. He could hear the arousal in her voice.

"Move the seat back, Dylan. Don't talk or I might chicken out."

He did. She reached down and unzipped his pants.

He was about to tell her she didn't need to do this, but she put her finger on his lips.

He kept quiet. She tried to fish his cock out of his pants and realized it wasn't going to be easy.

He undid his belt and his pants then peeled his pants and underwear down.

He knew by what she had done she was expecting an average sized cock.

His nine inches of steak was fully exposed, pointing up, way past his bellybutton almost to his chest.

Her reaction was positive.

"Oh my god."

She gripped it with her right hand. Her fingers wouldn't wrap around it.

"Yeah, it's kind of big," he told her.

"That's an understatement."

She lowered her head and began running her tongue up and down the length of his cock. His hand caressed her scalp. He liked how silky her hair was.

After a few minutes of licking his shaft, she grabbed it, and licked the frenulum, the sensitive underside. Precum was flowing from the urethra. She licked it up.

He clearly liked the direct pressure she was giving his frenulum while she jacked his cock. She could feel it swell.

She opened her mouth wide, glad she had a large jawbone, and took the head and another inch of Dylan's cock into her mouth.

It wasn't long before he warned he was going to cum. She sucked harder wanting to feel his seed shoot into her mouth. She swallowed as fast as he pumped it out.

He praised her afterwards. She told him he and his penis provided her plenty of motivation.

While she didn't mention Bob by name, she did tell Dylan, "I haven't done that in a long time."

She thought she should go inside. He pulled his underwear and pants up, zipped his pants up after buttoning them and buckled his belt.

He noticed she was watching him as he did so. He sensed he had sparked a hunger in her.

He thanked her again, "You didn't need to do that but I'm so glad you did."

She disagreed, "I needed to. I'll explain later, but it's complicated. I'm glad I did too. You taste good Dylan."

He laughed, "Must be all the pineapples I eat."

He wasn't hesitant about kissing her goodnight.

She got out of the car, but before she headed inside she put her head inside the car and kissed him again, "Call me."

"I will. Are there any times I shouldn't call?"

"No. Anytime you want to call is fine."

She reminded him, "I know it's hard not to, but think of Bob not as my husband, but more like my manservant."

He knew Bob was waiting for Jean and he felt a bit jealous.

"What are you and your manservant going to be doing when you go inside?"

She smiled, "I can tell you what we won't be doing. I won't be doing to him what I did to you and we won't be having intercourse."

Her answer satisfied him.

She added, "It's nice to know you're a bit possesive. Just realize I am married and plan to stay married. This won't work without compromise."

"I understand," he said, not sure if he really did. The concept he thought was so strange, but he was willing to give it a try because he really did like Jean.

Dylan watched her walk up to the door. He didn't back out of the driveway until he was certain she was inside.

He thought to himself, "One day I'll be walking through those doors with Jean and Bob be damned."

Once Jean closed the door, her thoughts shifted to Bob, her sweet cuckold husband. Their marriage she thought had really changed. She felt a bit giddy as her night had been so unbelievably good.

She had been very tempted to invite Dylan in and have sex. She couldn't believe she had been so risky and aggressive, performing fellatio on him the first date and in the driveway.

Part of her hoped a neighbor was peeking out the window and saw them kissing and she lowering her head to his lap. She felt strong and empowered and horny.

No surprise Bob was laying on the couch watching the television, wearing nothing but the pink cage he insisted on wearing because of the way it made him feel.

She reminded herself to not be too hard on him and to adopt a different persona. His submissiveness and longing to be a cuckold had changed him from the man she fell in love with. He wasn't a stranger, but there were times she had been filled with resentment.

She was now realizing the changes in him had liberated her and were necessary. She still couldn't help feel a bit sad as one door closed and another two opened.

She really did love Bob but she also thought she could fall in love with Dylan. She resigned herself to having two distinctly different relationships with the two men, wondering if she would to integrate them. For now, the answer was no.

She walked into the living room.

"There you are. Did you get everything done that I asked you to do?"

He sat up feeling a bit self conscious and ashamed of his fetish and its hold on him.

"Yes, Mistress Jean, I did. Everything on the list."

"Good boy."

She looked around the room.

"Get on the floor. Move the coffee table out of the way. On your back."

A minute later she was riding his face. She hadn't even bothered to take her panties off, just pulled the crotch to the side.

Bob had always been good with his tongue and that night he didn't disappoint his mistress. Then again, she had been extremely aroused when she walked in the door.

After her orgasm, which left his face soaked, she got off of him.

"Thanks cuck. I needed that."

She thought about just going to bed but decided he had been awfully well behaved he deserved a reward.

"Go get the key."

He removed his cage. They sat on the couch. She gave him a handjob as she told him how good her date had been and how they were already making plans to go out again. She didn't ask how his night had been or apologize for not calling.

She did think as she pumped his cock how small it was compared to Dylan's. She had no interest in sucking him.

It didn't take long before she had him spurting streams of cum all over his lower belly.

"After you clean up, you can get me a glass of water and put your cage back on."

She had rarely shown interest in his chastity, but that night it just seemed to make sense. She thought if it's inaccessible she wouldn't be tempted and she really felt tempted to have intercourse, not so much because of his penis, but wanting to feel the closeness.

"Let's go to bed. I want to snuggle, but I'm too tired to talk right now. We'll have plenty to talk about tomorrow You can tell me all about your night then."