When you live with someone for a long time it is easy to pick up on nuances that things are not quite right and so it was on Saturday morning when I woke up. Ellen had come in very late and I had been up a couple of hours when she sleepily padded into the kitchen for her morning coffee. She was wearing her silk robe, it was loosely tied, open and her breasts almost exposed. On her left breast, near the nipple, was what looked like a small hickey. I didn’t say anything, but from her actions, averting of eye contact, I waited for her to start.

“How was your evening?” I asked.

“In ways it was great,” she said, “but in other ways I’m feeling a bit guilty”

“Go on,” I said.

“Well his name is Case and he said he wanted to give me a traditional date, and he did. We went to a movie you wouldn’t like, had a burger and beer, and then danced at a country dance hall. He tried to teach me the Texas two-step. We had fun.”

“You feel guilty about that?” I asked.

“No, it was a traditional date, like I said,” she continued. “So we made out in the theater and parked for a little while on the way home.”

I tried not to display any emotion, knowing that how I reacted could be taken the wrong way, but I suddenly had a concern or two of my own.

“Well, I guess parking is considered a part of dating,” I said, adding, “So how far did he get when he parked with you?” 

“He had my breast out kissing it,” she said, “and I really am sorry and feel guilty about it. I had a buzz and it seemed to happen so naturally and it felt good, it felt really good.”

“That what you feel guilty about?” I asked.

She paused, looking me square in the face. “No, because I stopped him and had him bring me home. I feel guilty because I didn’t want to stop, I wanted to go further.”

“But you did stop.”

“Yes, but this is something we have to talk about. I’m not sure I can keep doing this with all these different guys and stopping. Especially considering both Fred and Case want to go out with me again,” she said.

“What do you want to do?” I asked.

“I don’t want to lose you over a stupid bet,” she said. “If you want to stop it we’ll stop it right now, cleaning Mark’s house once a week can’t be all that bad.”

“You like the dating?” I asked.

“I’ve only been on two and both were fun outside the kissing and stuff,” she said, “but I wouldn’t trade it for being married.”

“Well, to be fair with the bet, you did say you would go on 10 dates,” I said.

“But what I just said,” she stammered.

“I heard what you just said, you said that if you keep on there is no guarantees, that some of your dates might get lucky and end up fucking you.”

“Yeah, I guess that’s it.”

I thought carefully before I continued, but I was having my own little mind fantasy of my own, imagining my wife parked in a pickup with a stranger and her boobs pulled out for him stuck on. “Well, the possibility of things going further is a given in dating, is it not?” I said, “So to truly test the theory that has to be a possibility on the table.”

She looked at me seriously. “Are you telling me that I have your permission to go further if I get carried away and want to and that you’ll not leave me over it?”

“I guess that’s exactly what I’m saying. If you were single and went on a date you’d be free to do what you want or it wouldn’t be a real date.”

“I didn’t have that in mind when I made the bet,” she said.

“I know,” I replied, “you didn’t make the bet so you could go out and get laid by someone new, but a by-product of this bet might satisfy your curiosity about the dating life you missed.”

“Even if I end up getting laid?”

“Even if you end up getting laid.” I answered.

“I can’t believe I’m hearing this. This is not the same jealous type I married years ago” she said.

“I guess that part is right,” I said, “but there are conditions.”

“What conditions?”

“Well I want to know where you are at all times, this waiting up until almost 2 not knowing isn’t safe,” I said.

“And?”

“And just like now I want to know every intimate detail, holding nothing back. I want complete honesty from you.”

“Fair enough, I can promise that. And?”

“And I want the same privilege, if I find myself attracted to someone during this dating bet I want to be able to explore that for myself as well,” I demanded.

She paused on this one, obviously uncomfortable. “You have someone in mind?” she said, from the tone of her voice I could tell she felt a bit threatened.

“No one at all,” I said, “but what is fair for one should be fair for the other.”

“Only during the time of this bet?” she asked.

“Yes, just through the few weeks of this bet.”

She smiled to herself. “This could be fun,” she said, mentally drifting off for a moment—a knowing smile on her face. She wasn’t thinking about me at that moment.

The weird part of it for me was I realized as well that I was looking forward to it too.

She snapped back out her little daydream and came over to my chair, opening her robe and letting it slide off her shoulders, scooting my chair back and her hand reaching inside my boxers and pulling my erect cock out. She fell to her knees and sucked me for a few strokes before standing, straddling my chair as she guided my cock inside her and fervently fucking me as she described in low whispers how Case had sucked on her breast when they were parked and how much it has turned her on.

 


 

Week 1 Date 3 - Trent – Saturday

 

I don’t know what I was expecting when I admitted my guilt to my husband about getting carried away with Case. It certainly was not permission to go further—even though that is what I was given. But it did make sense, at least within our thinking at the time. Of course there was that knowledge that there was nothing holding me back now either.

We had a brunch and Des left at lunchtime for his monthly golf game with his friends, and I prepared for my date. Mark had emailed a photo and details on how should I dress. He said be ready by 5:00 p.m. and wear something casual. This time Mark had added, “Wear something sexier than usual.”

From the photo of Trent I could see he was that he was strikingly handsome. And very well built, as the photo showed him in swim trunks on a beach.  A hunk. I started thinking what “sexier than usual” might be, thinking to myself, “sexier with him will not be a problem”.

I elected wear a short jean skirt, let my hair down and a tee top with spaghetti straps that was a little on the thin side. I first put on a strapless bra, looked myself in the mirror and didn’t like the way it looked and took it off. I pulled the soft cloth tight over my boobs to be sure it wasn’t see-through. It wasn’t, but it was obvious that I was braless underneath. “That’s sexier than usual for me,” I said to myself. In respect to modesty I did put on a light wrap. Since I was feeling especially sexy today I put on my skimpiest thong, which then required a trip back to the bathroom for some extra trimming of my pubis.

Trent ran the bell promptly at 5:00 p.m. and when I opened the door I found him to be even better looking than his photo, with a deep resonating voice. “Hi, I’m Trent,” he said, extending his hand, and I did mine which he took and kissed—not the peck on the back of the hand but a knowing kiss between first and second knuckle. The mere touch there sent a tingle through me. This man knew what he was doing around a woman—and I was that woman today.

“Wow,” he said, stepping back from me, “Where have you been hiding? You’re hot!”

“Thanks,” I replied, “let me get my bag and we can go.”

Trent had a small SUV and we took the route out of town, turning off and heading up into the mountains, talking about places we’d been, our mutual friendship with Mark and how this entire dating scenario had come to be. He was a good conversationalist and after three sentences it was like we had known each other for years.

“I’m delighted that I have this opportunity to spend some time with you,” he said. “I’ve been looking forward to this since Mark showed me your photo.”

“Where are we going?” I asked.

“I guess saying it is a surprise is a little too vague. We’re going one of my favorite spots on West Hills Point for a little picnic.”

“I’ve not been on a picnic in years,” I said.

“That’s even better,” he smiled.

Trent stopped for gas while I called home on my cell phone. Des wasn’t home, I left a message telling him where we were going, and a giving him a quick “I’m having a great time,” and “I love you”. As I said it I made up my mind since this was my date I didn’t want to spend it worrying about Des or feeling guilty. I turned off my phone. I was putting him out of my mind until we got back to the city.

We continued driving up through the mountains until we stopped a few hundred feet from the top of a large rocky point. “We walk from here,” Trent said, opening the back and taking out a large straw picnic basket and a small cooler. I followed him up the winding trail, coming around a large bolder to a small grassy spot flanked by the boulder on one side and a rocky slope on the other. A large pine cast its shade over the grassy area.

We were facing west and the sun was starting to touch the horizon, brilliant orange and red streaks of light with dark purple clouds dotting the sky.

“Wow,” I said, sitting down on the thick blanket he had spread out in the grass.

“Great, that’s the reaction I hoped you’d have,” Trent said, sitting down by me. “I’ll get out the food and wine, but for the next half hour or so don’t talk, enjoy this magnificent show that nature has provided.” I nodded. He opened the basket and spread out a table cloth, poured some very cold Chardonnay from a bottle in the cooler, and fixed plates of fried chicken, coleslaw and potato salad, obviously catered from a very nice restaurant.

We drank the wine slowly, ate slowly, staring at one of the most beautiful sunsets I’d ever seen. It was moving.

We were still watching when he opened the second bottle from the cooler and I started to speak but he put his finger up to my lips, “sssshhhh, watch.” And I did. I took my wrap off and saw him looking at me now as well.

Trent quietly put the dishes in the straw container and moved it to his left behind me.

The last of the sun itself dipped behind the hill and it was like a color explosion in the sky. He moved behind me and wrapped his arms around me and held me there as we continued enjoying the sunset.

Trent was kissing my neck and the sensation while watching the sunset was perfect. As the day turned darker and the sunset faded he whispered, “OK, you can talk now.”

“There’s nothing to say after seeing that,” I said. I turned to meet his kiss and together we lay down on our sides on the blanket, kissing for long minutes. I was buzzed from the wine, high from the sunset and turned on by this hunk kissing me. I knew what was going to happen probably before I had left home, but now I was rolling in the passion of what I could only consider the perfect romantic seduction. It wasn’t a complete seduction yet, but it was heading that way.

I returned his kiss, our tongues touching and felt his hands moving to my breasts beneath the thin top. My first reaction was to resist, but I didn’t. I had no reason to stop him and I didn’t want to stop him—in fact I wanted him to go on very badly.