One Weekend a Month Pt. 01

(Part 1)

Damn, this guy is thorough. As I looked through the questions, I smiled, not believing we were at this point. Ashley, 'Ash,' and I recently celebrated our 28^th anniversary. Our oldest daughter got married last year and our other daughter is a senior at UNC. We've always had a good sex life, but when the kids moved out and Ash hit 45, her libido went into overdrive.

Being empty-nesters, we re-discovered ourselves. We began role-playing, using toys more often, some light bondage and just having fun with one another. We read erotica at night, each selecting stories that interest us. If something turns us off, we move on to the next one, but we've found the more we read, the more open we were to certain things, at least in fantasy.

We married young, and while I had been with a few girls in high school and college, Ash was a good girl and was going to save intercourse for marriage. She would give hand jobs and blowjobs, but no sex. She did end up giving in the night we were engaged though, and she was insatiable. I guess 22 years of pent up sexual energy was too much, and we've a good sex life since. Sure, when the kids were little, we would go weeks and even longer, without any 'us' time. Even when we did, it was usually a quickie just to satisfy an itch. Now they are grown and out of the house, it's a different dynamic.

We've talked over the years about her regretting not experiencing someone else. I've been open to it, especially lately. I'm comfortable enough in our relationship, so we began role-playing her being with another man or two, while I'm watching.

A few months ago, we were out on the boat and I had just climaxed. As I typically do, I went down and started eating her out. This is something I've done for the past few years, well at least since she hit her sexual prime. She had never orgasmed through intercourse before, but one night she was the closest she had ever been just as I unloaded inside her. I felt bad she was so close, that I just went for it and brought her to orgasm with my mouth. I didn't even think about the fact I was licking up my deposit. I just wanted her to finish. And she did. It turned me on so much that my erection came back and we went at it again. She had an orgasm while I was inside of her this time. That was the first orgasm she ever had from intercourse and she has been having them ever since. It was though something 'clicked', and now she climaxes through intercourse most every time we have sex.

So, as I was cleaning up the sizable deposit I had just left, I could tell a good clitoral orgasm was approaching, topping off the vaginal one she just had. Ash gets vocal sometimes, and she started using language that would make a sailor blush. Finally, just as the first wave hit, she was yelling, "Oh, god, yes, yes, yes! I want that to be another man's Rich, clean up your slut wife's used pussy."

As her orgasm subsided, she was in that blissful state. Yes, I had heard what she said, but wasn't sure if it was role-play or a statement of fact.

"I'm sorry about what I said. I was caught up in my orgasm that it just came out. I'm sorry babe." She said as she sat up and looked guilty.

"There's no need to apologize Ash, we've talked about this and I know you would like to be with someone else. I want you to, but you have never seemed open to really doing it before."

"Are you being serious? You would not mind if I were with another man? Letting him take me the way you just took me?" Our eyes were locked for a few moments, when she looked down and saw my raging erection. I had recovered quicker than usual, and she certainly noticed.

Her look of guilt turned to a grin, when she asked, "Does it turn you on to think about this becoming a reality? Not fantasy, but for real?"

"Yes. The more we have read about hot wife and cuckold stories, I fantasize about it all the time."

She didn't say another word, she just leaned down and took me into her mouth. She gets drenched when we fuck, especially if we've been naked all day on the boat, and today was no different. My cock was covered in her slimy secretions, mixed with my semen. She took me all the way in, choking as she did. She doesn't deep throat often, but she was revved up. Several minutes of this oral assault was too much, and I blew my second load in 20 minutes.

She pulled up, showing me the deposit I left in her mouth. She swallowed, making deliberate noises as she did. Smiling, she said, "Just imagine that was someone else's cum." She licked her lips and looked down as my shrinking cock bounced.

The following weeks, we were fucking more often than usual. She would tease and taunt me, talking about me watching her fuck another man. Watching him slide his cock into her pussy and then me clean up afterwards. It was after one of these sessions early one morning when I finally said,

"So, when do you want to look for someone?"

"I've been waiting on you to bring it up, but since you have, I'm ready to start looking."

"Okay, let's post an ad on one of the swinger sites and see what happens. I'm sure it won't take long to find someone." I got up to use the bathroom, grabbing my iPad on the way back to start looking at sites.

"Wait, let's talk about boundaries first. I've been thinking about this a lot too, nonstop since we talked on the boat. The more we have read about hot wife and cuckold relationships, the more it turns me on as well. BUT, we have a great marriage, and I don't want to jeopardize that."

"I don't want to jeopardize anything either Ash. It turns me on to think about watching you with another man. I can't get it out of my head. You've said for years now you somewhat regretted not being wilder before we met and that you sometimes wished you had been with another guy or two."

"I know, and I do. I do want to explore this, but I also want to set some ground rules." She said as she stood up and started putting on her clothes. "Get dressed and let's go sit outside and talk."

As we sat down with a cup of coffee, watching a boat coming back in from fishing, she continued, "I've noticed the stories you have been selecting lately are more about cuckolding and not wife-sharing. I've read a few blogs on cuckolding and it does seem to fit with you. You were successful in business and have always been type A. Ever since you sold the company and retired young, I think you are bored. While you like the idea of watching me with another man, I think you like the idea of not having control as well. Am I right?"

"When you put it that way, yes. I have fantasized about that. I've never been submissive, but the stories we have been reading, I don't know, I find myself consumed thinking about it all the time."

"I'm willing to try this, but like I said, there will have to be ground rules."

"Ok, what are they?" I was already turned on, just having this conversation, but it was looking like this could really happen.

"I will select the guy. If we are going to do this, I must be attracted to him. I also want to have the freedom to be with him alone if I'm comfortable, as I'd like to explore with another man without having you judge me on how I act." She took a sip of coffee as she waited for my response.

"I've thought about that. You being with someone while I'm not there. It's something that both turns me on and scares me. But I think it turns me on more." It does turn me on more, as my cock was hard as a rock hearing her tell me she wanted to basically go wild with a guy with me not watching.

"This also isn't going to be something we do all the time. I love you and love sex with you. But, I would like to explore with another man and live out some of the things we've been reading about. I want to do it alone, and with you watching. If at any point, I feel it is harming our relationship, it ends. Okay?"

"Agreed."

"Let's set up a profile and see what happens." She said as she took the iPad from my lap.

We created a profile and selected a 100-mile search, as we live outside Charleston now and it isn't that large a market. We didn't include a photo, which I knew would not get as many responses, but I didn't want a photo out there. We had a few responses, but I don't think these guys read our ad. We were very clear this was going to be an enhancement to our marriage, and not a full-time thing. We responded to one guy, who seemed promising, but after a few more emails, he ended up just wanting photos to jerk off to.

We expanded the search to 300 miles, which now included Raleigh, Charlotte, Atlanta and Jacksonville. Talk about a shit show! We had almost 100 replies the first day. All the guys posting cock pics and overly aggressive. Maybe this wasn't to be.

We tried another site, but similar results.

Regardless, our sex life was in hyper-drive. Just the thought of her taking a lover had both of us so jazzed, maybe just the fantasy was all we needed. We checked daily at first, then every few days, as the responses started waning.

....

I had left before dawn on Wednesday morning, to a new spot I'd learned about 10 miles off the coast the week before. Ash plays tennis at the club on Wednesday, so that's my fishing day. I had just pulled the boat back in before dark, having an awesome day catching dolphin (Mahi Mahi) and snapper. Ashley met me on the pier as I was washing the boat down on the lift. Her smile told me something was up, but I wasn't sure what.

"Ok, you have a look on your face I can't read. What's up?"

"I think I found him."

"Who?" It had been weeks since we placed the ads, and I had all but given up on finding someone.

"His name is Brian." Her eyebrows were raised as she smirked, thinking I couldn't be serious.

"OH! Well, tell me about him." I felt the tingling sensation in my groin, as my cock started to wake up. Great day fishing or not, this had my full attention.

"Finish with the boat and take a shower, then we will talk." And with that, she turned around walking back towards the house.

My cock was hard as a rock as I stood under the warm water. I was disappointed we hadn't found anyone, and thought it may never happen. While I can't explain it, I really do want her to cuckold me.

"OK, so, tell me about him!" I said as I handed her a beer and opened one myself.

"He is 48 and a widower. He and his wife were swingers before she passed away three years ago from breast cancer. He liked the dynamic of the lifestyle and decided to look for a couple to cuckold. He found one couple and said they had a lot of fun, but they stopped seeing each other a year ago, as 'life got in the way'. He didn't elaborate, but I didn't push it either. He said he is an attorney, with his own practice in Charlotte."

"Charlotte?" I asked as I took a swig.

"Yes. He has been searching for another couple for a while and has been looking all over the southeast. He saw our ad and thought we may be a fit."

"When did he respond?" I asked as I was taking this all in.

"I checked the site last night after you went to sleep. He responded two days ago, so I replied. When I woke up this morning, after you left, he had responded again and I've chatted with him all day. I think he's a great fit, but he wants to get to know us better before we do anything. Just the fact that he isn't ready to set something up immediately lets me know he isn't one of the many time wasters we've responded to.

He asked me a lot about us, and realizes this is a kink for us and something we want to use to enhance our sex life. He also asked what I want and wanted to get out of this, as it's usually the guy pushing this kind of thing. So, I told him some of my fantasies."

"What did you tell him?" I interrupted, as I was a little too excited.

"Well, if you will let me finish." Looking at me with that look she gives when I do something stupid. "He sent us both a questionnaire. I'm still going through mine and I forwarded yours to your Gmail."

"Questionnaire? What is this, a quiz?"

"No, after reading the questions, it will all make sense. He has obviously done this before and is very thorough. Anyway, this is one of his rules if we are to meet. Why don't you go inside and check your email? I'll start cooking and we can talk more over dinner."

"You weren't kidding, he is very thorough." I sat at the table after looking through the questions.

"Yes, but I like that he's taking his time and wants to know what we do and don't want to experience. I won't ask how you are going to answer some of your questions, but I think we may be exploring things we've never really discussed before." That smirk again.

He asked about most everything. Numerous questions on sex, sexual experience, kinks, limits, fantasies, toys, but also any health issues, STDs, phobias, hobbies, favorite drink, food, income, etc. Many of the questions looked more like a psychiatric profile. I was honest in my answers, all of them. The one thing I've come to realize in my 50 years is that I'm open to things now I never would have been in the past. And, I'm comfortable enough in who I am to not be ashamed of what turns me on.

"So, are you even going to show me a picture of him?"

"Are his looks important to you?" Smirking again.

"No, but if I'm going to spend hours answering that thing, I'd like to know what he looks like."

She turned her phone around and showed me a photo. He is a handsome guy, fit, probably my height, blue eyes, brown hair with a hint of grey.

"How about his..." Before I even finished my sentence, she said,

"Cock? You want to know about the cock that may be fucking your wife?" Smiling again, knowing it was a fair question. "He didn't send a photo of that, just the one I showed you. Let's go to bed and we will answer the rest of the questions later. This has me so turned on, I hope you have a few rounds in you." She grabbed my balls and gave them a gentle squeeze, as she dropped her dress, walking down the hall to the bedroom.

Sex was primal that night. I had just shot my second load into Ash's pussy when she shoved my head down again. As I was licking her pussy, her hair all wet and messy from our combined juices, she grabbed one of her dildos and started sucking it.

"This is Brian's cock I'm sucking; does it turn you on?"

"Mmmhmm" It did. She pushed my head away and shoved the dildo into her pussy, fucking furiously on the glass phallus. She had a strong orgasm, bucking and writhing as she came. As she pulled it out, she put it to my lips, pushing it inside my mouth. Her juices taste wonderful on the glass, and she left it coated from how wet she was.

"That's Brian's cock you are sucking, you know." She smiled at me as she grabbed my cock, which was hard again. We went at it once more before passing out from exhaustion.

The next morning, over coffee, we each completed our respective questionnaires and hit send. He responded within a few minutes and said he would look over them and be back with us. Later that afternoon, we received another email with two attachments, one for each of us.

They were follow-up questions to our responses. After another hour of clarifying, we both sent separately. This seemed like over-kill, but he seemed to know what he was doing, so we both played along.

It was Friday morning when he responded. A short email, only saying:

I would like to see a photo of the two of you. Nothing x rated, just something that shows who you are. Be natural.

Every guy we chatted with always requested naked photos of Ash. This guy was different. It seems he gets it.

"Do we have a photo we can send? How about the Facebook photo on your profile page?" I asked, as Ash now looked to be deep in thought.

"No, let's take a new one. I want to get ready for it first." As she got up to walk back inside.

"Get ready for it? He just wants a quick selfie, no need to overthink it."

"You don't understand. This is important to me, so I want to look my best."

And with that, she disappeared into her closet. Numerous outfit changes later, we started looking for the 'right spot' for our picture. We ended up on the pier, the boat and river in the background. Finally, this 'quick photo', three hours later, was ready to send.

Ash wanted to go out on the boat after we sent the photo, so we loaded up a cooler and headed out. We hadn't even hit the pass before she was out of her clothes and putting on sunscreen. Damn, I was loving this life. I started navigating around a sailboat before we were in open water when she started unbuttoning my pants. She leaned over and took my cock in her mouth, as we were passing the boat. Two couples, all four staring over at us as we passed. They no doubt saw her naked back as she leaned over my lap. I got a thumbs-up from one of the guys as I throttled up heading east.

Ash briefly sat up, exposing her breasts to the two couples. She waved at them, and went right back at it, bobbing her head up and down on my cock. She reached her hand down to her pussy and brought her fingers back up, putting them in my mouth. She was already drenched, and tasted yummy. She worked my cock for a few minutes when I felt that sensation, I'd already reached the point of no return and a few moments later I blew my load.

She kept my cock in her mouth until I started shrinking, swallowing everything I gave her. As she let my cock slip between her lips, she stood and kissed me. I could taste myself on her as she stuck her tongue down my throat.

"Doesn't Brian's cum taste good?" She asked, as I swallowed the rest of what she had transferred into my mouth.

We spent the day fucking, talking about Brian and having fun. It was almost dark when we got back to the pier. We cleaned the boat and headed back up to the house when she checked the email.

Nothing.

"He's probably busy. With as much interaction the two of you had, and the numerous questions we both answered, he's probably still reading." I said as I headed for the shower.

She woke up first Saturday morning and was already on the deck drinking coffee when I joined her.

"Good morning beautiful, how did you sleep last night?" As I kissed her forehead.

"He still hasn't responded." Looking at the water, as the light in her eyes was gone.

"Ash, it hasn't even been a day, he will respond." I took a sip of coffee as I sat down beside her.

"It was the picture. He doesn't find me attractive and that's why he hasn't responded."

"Are you fucking serious? You are being ridiculous! Of course, he's going to find you attractive, because you ARE attractive."

"You don't understand. I'm 50, I have greys showing through no matter how often I color my hair, my breasts are sagging and I'm just old. He's not interested."

"Ash, he knew how old we were before we sent the photo. You are being silly. He is probably just busy or something, but he will email back, I'm sure of it."

It was Tuesday and still no word from Brian. I couldn't believe he wouldn't have found Ash attractive, but he hadn't responded. In all previous communication late last week, he responded within minutes. Now, here we are four days since the photo, and no response.

Nothing.

Ash was in a funk. The mojo she had from not only searching, but talking with Brian, was gone. She was genuinely depressed. We talked about it and she said it was a rejection she had never felt. She so wanted this to work, but more so, just to feel like another man would want her. To be attracted to her. To find her fuckable.

I gave her space, and felt stupid for us going down this path. We should have just left this fantasy and not tried to do this. It's just not worth it.

Wednesday morning, I headed out fishing. I told her I'd be back early and we could go out to dinner. I thought maybe that would take her mind off things and we could get some of that spark back.