Rosie

When I entered the Coffee Cafe, Olivia was already there. I walked up to her and asked, “It’s just us?” When she nodded, I went and ordered soup and a ham sandwich, and then I came back to her table. There were often six to eight other women here, but you never could be sure.

I had a couple of things I wanted to approach Olivia about, and I was hoping we’d be alone. I suppose I was sensitized by what I had learned about my parent’s cuckold marriage when I was nineteen, and I had questions about Olivia and Ross and cuckolding. 

I sidled up to the topic when I talked about the last party we’d attended. I started by saying, “Did you notice Heather and Bill? I thought they were going to do it right there at the party. It was pretty clear what was happening.”

Olivia replied, “I felt uncomfortable for Tom. Having to see your wife act like that, and he didn’t seem to like it.”

We gossiped about Heather and her tendency to overdo it at parties. We also discussed the question, was she overdoing it? Maybe he likes it too.

We moved to the music and dancing, and just as we were finishing I added,” You seemed to enjoy flirting last Saturday,” with a smile, I continued “Wasn’t it a bit embarrassing with Ross there? It looked like a scene from some Cuckold Movie.” 

Olivia hesitated and replied, “Not a bit, Ross doesn’t mind, I think he enjoys seeing me flirting.” 

I replied with a laugh, “Well then, there was a lot to be enjoyed. Oh, did you catch Greg's joke about the daffodil?”

Olivia laughed, “Yeah, I could relate to it, Daisy, my sister, has been sharing some hospital stories. I don't remember one that involved using a daffodil as an anal thermometer though. With that, we cleaned up the table and walked back to work laughing about some of Gary’s jokes, bad dirty jokes.

That evening I got a call from Olivia, “Hi Rosie, I was just sitting here and I was thinking about lunch and the party last weekend. You commented that it reminded you of a movie of some sort?” She ended the sentence as a question.

 I paused then answered, “A Cuckold Movie.” Hesitating I continued, “I had a boyfriend and he liked cuckold porn, and some of the cuckold movies started with wives flirting, heavy flirting with the husband watching. Olivia, I didn’t mean anything with the comment.” 

Not exactly true, but close to the truth.

Olivia’s response was, ”Um, I don’t know what a cuckold movie is.” 

I hesitated to think for a minute and then said, ”Well, what Joey liked to see was wives that had boyfriends, and their husbands got off on it. He loved to see wives do things with their lovers that they wouldn't do with their husbands. He especially liked to see the husbands watch and get themselves off while watching their wives.”

Now Olivia hesitated, “Men don't do that. Do they? It sounds unlikely to me.” 

I paused then, said with a little smile in my voice, ”They don't like to watch cuckold movies or they don’t like to watch their wives get fucked in front of them?“ I continued, ”Olivia, I can attest to yes in both cases, some of them at least. I guess I was wondering if you and Ross have an agreement.” Olivia hesitated, so I added, “Do you have questions?”

When she nodded, I said, “Today is Friday, um maybe on Saturday we can meet, and I can tell you what I know about it.” 

We finally got to it. I’d been seeing things between Olivia and Ross that made me wonder. Was it just Olivia? Or did Ross want it too? I get a lot of vicarious pleasure watching as my friends approach cuckolding their husbands. Well, I don’t make them drink from the stream if they don’t want it. 

Saturday, Olivia and I were sitting in the back of Tony’s. We got back to talking again about flirting and how Ross seems to enjoy it. This is where I grinned and said, “Do you enjoy the attention, especially in front of Ross? It sure seemed you got off on it, and Ross too.”

Olivia smiled, “I do enjoy flirting. But you said something about cuckold porn.”

I answered, “It reminds me of Joey's Cuckold Porn, C.U.C.K.O.L.D, Cuckold porn, where the wife fucks other men and the husband gets off on it.” 

This is where I hesitated, “Several years ago, a cuckold relationship. I learned about it at uh, nineteen. Actually, it was my Mom and Dad. A friend noticed Mom's flirting and talked to Mom privately and told her about cuckold relationships. She told Mom that she could increase the teasing with more direct innuendo, touching, and kissing; Dad would probably still enjoy it and might even want her to go further to having sex in front of him.” 

I paused again, thinking. ”My Mom hesitated at first, but Susan, that's her friend's name, Susan, said “If you might be interested, there are a couple of ways forward. One is you do some role-playing with Mike and see how he responds; the other is to just start increasing the flirting and touching and see how Mike, that's my Dad, responds to the flirting. And how he responds at home, talking about what just happened.”

I paused here and asked her if this was too, just too much. I think both Olivia and I were turning a little red. I told her how I found some DVDs and when I played them I saw they were people fucking, the woman sucking the guy's cock and the guy eating the woman's pussy. It was triple X-rated. It wasn't until the third DVD that I realized it wasn’t just some random porn, it was my parent's videos. Videos showing my Mom fucking other men, my Dad, Mike, being cuckolded.

I continued. “I learned more about my folk's cuckolding relationship and a little about how. Once they knew I’d learned about it, they, uh, Mom mostly, shared more about what they were doing.

“What's important though is what this says to you. I can’t say for sure, but, I watched Mom and Dad and some of their friends that they introduced to cuckolding. The dynamic I saw is often similar to Ross and your relationship. “I’ve seen it develop lots of times and for some, it was exactly what they wanted and others, that Mom knew about, ended up breaking up the marriage.

“So, My first question is. Olivia, do you want to change the subject now, or keep discussing cuckolding?”

At this, I just stopped talking or moving for a minute. It seemed like several minutes. Then Olivia quietly said, “Let's continue, and when I get all I can understand, I’ll change the subject.”

“Okay, am I being too graphic Olivia?”

Olivia hesitated, ”Be as graphic as you need. Let’s get a soft drink and move this to the park across the street. With, uh, more privacy”

We found a table that was separated from the others and sat down.

I started first, “She saw a lot of couples make mistakes. They varied from desperately unhappy marriages to vicious divorces. Mom talked about aftercare, something she learned from reading BDSM literature. But, she also said each couple was different. 

“I never saw any humiliation or disrespect in their relationship. Never. Well until I saw the cuckold videos. In their normal life, never, and she swore there was no gratuitous humiliation in their private sex life. When I met other cuckold couples, Mom wasn’t unique but she wasn’t the typical cuckoldress wife either. Some of the cuckoldresses seemed to want revenge on the patriarchy. That was Mom’s view at least.

“Is any of this speaking to you, Olivia?”

Olivia sat thinking for a minute then took a sip and slowly said, “Um, I think, uh, maybe? I think I might enjoy it. Cuckolding Ross? Fucking other guys. Maybe?” She looked at me, “Um … you know Ross. Do, do you have an opinion? What would Ross say if I just came out and asked him? How do you see Ross reacting if I just did that, emulating your mom? Or should I just forget it?

I paused, thinking, “What I would do? What I would do first is check any computers in the house. Especially ones you don’t normally use. Some things I’ve heard about are browser history, hidden folders, and hidden browsers. Just to see if he’s looking at cuckold porn. If he is, you have an opening to ask him. If he isn’t well, you can test him.

“Would you like to get together for lunch privately? Bring lunch and meet somewhere else maybe drive together to a park? Would you have time to check out your computer?”

Olivia answered, “Yes, I think yes, we do have a second computer in our extra bedroom that I don’t use much, it’s Ross’s. I could check it easily. Where should we meet, Rosie? Do you know where my parking space is?”

I nodded as we got up to leave.

Olivia

As I left, I was thinking.

I enjoy flirting and sometimes I have wondered what might happen if I took some of it seriously. I was thinking of cuckolding Ross. After talking to Rosie I realized I was thinking about fucking someone else, being fucked by someone else. In front of Ross! Shit, in front of Ross. Ross watching me being fucked. Ross kissing me while I’m being fucked. This sounds erotic as Hell. Would I want it, would Ross want it, would Ross even tolerate it?

When I got home, there was a note, Ross was helping Steve move some stuff. Okay, I had time now. I opened the computer and Chrome looking for the history. Nothing interesting there. Maybe he wasn’t looking at cuckold porn. 

Then I remembered what Rosie said about hidden browsers, and I remembered we had tried out Firefox. I couldn't find it where it had been. Then I searched and it came up. Hiding in an obscure folder, where no one would see it unless they were looking for it. 

When it opened and I checked the search history. There it was, his porn habits in front of me. I was looking at his favorites and it was full of cuckold stuff. As I opened them, it was clear, what he was into; cuckolding, cheating, hotwives, and submission. When I opened up the forums, I was logged in automatically. I closed down the computer leaving no trace, I hoped.

I went to lie down and think. A bit later, I texted Rosie asking if we could talk. I had just put my cell down when it rang. When I answered Rosie started, “That was fast. You must have found something.”

I told her what I found, and what it took to find it. Chrome was clean but I found a hidden Firefox. “I’m going to need hours to see most of it. I need help getting Ross away from home for most of a day. I suppose I could do it at night, though I would be worrying Ross could wake up. I could use your help too, making sense of it.”

Rosie thought a minute then said, “Olivia, uh, I may have an idea. Sam invited me to a Giants game tomorrow, it wouldn’t be, uh completely, surprising if he asked Ross to the game if I had to cancel, would it?”

I told her that no it wouldn’t. Rosie said she would call back in just a minute. When she called back, she had asked Sam if he would ask Ross if she canceled. She explained that I had asked her to help to plan a surprise for him. This would get Ross out of the way and let her help me. She laughed and added, “It wasn’t even a lie. We are planning a surprise for Ross. Shall I try to set it up? Remember, this is a favor you owe me.” She ended with a laugh.

We agreed and after an hour, with Ross checking in with me, it was set. Ross would be leaving by 10:00 Sunday morning.

Rosie came at about 10:30 and we got started.

Rosie

That was quick. Olivia must be really interested in cuckolding Ross. Now the question was Ross. Did Ross want it in real life? From what I’ve seen of him, watching Olivia flirt with other guys, I’d say that he thinks he does. 

Ever since I discovered that Mom and Dad have a cuckold marriage I’ve enjoyed watching as I’ve helped married couples fumble their way to consummate a cuckold marriage. I get a vicarious high from watching it happen.

First things first, I don’t want to ruin anyone's marriage, so I need to be sure the husband wants it too. When I am, it’s easy to guide the woman.

When I got to Olivia’s house, we sat down in the living room and talked for a bit before looking at the computer.

Ok, it’s tip-off time. Just getting Olivia to be thinking about cuckolding is step one. I  usually start by cautioning my friend about the potential problems while holding it out as exciting by bringing my folks into it too. So here goes.

I started by saying, “It sounds like you found a treasure trove of his fantasies, so now we need to figure out if he wants it in real life. Sometimes fantasies are just that, fantasies. Kind of like when you fantasize about being fucked by Brad Pitt. So let's see what we can find out.”

Olivia booted up the computer, started Firefox, and opened the history. As we read, we both laughed, lots of cuckold sites, oh my! We started with some of the forums. His name in most of the forums was “cuckoldwanabee” with two Es.

In some of the forums, it was easy to find his posts. They were all pulled out in a my-posts list. Some were comments on other posts, but some were his starting posts asking things like what is it like being cuckolded the first time? What is it like seeing his wife fucked the first time, or hearing her cum with someone else’s cock? How badly did wives generally humiliate the cuck? Did the cucks still fuck their wives or get cut off. How did cuckolding affect the rest of their lives? Did cucks have to submit everywhere?

We didn’t need to review all the stories to know he was interested in cuckolding. As we looked them over it became clear he avoided the real heavy humiliation type. He also read stories that showed a lot of affection between the hotwife and the cuckold. There were some chastity cuckolds but he had a lot more without. He avoided the mean wife, bitch stories. 

This is so much fun, learning about Olivia's husband this way. I remember my first friend whom I introduced to the excitement of cuckolding. That was Victoria and we met at my first job. After a few months, I knew that she would enjoy cuckolding her husband Ed. Her first sex partner was his brother Peter and she was never able to tell Ed that she was fucking his brother, especially after Peter got her pregnant. She was lucky that Ed never twigged that there was an open month and the only possible father wasn’t him. 

Listening to Victoria, was as erotic as learning about my Mom and Dad. How many friends have I helped discover their need to become cuckoldresses: Victoria, Emily, Kelly, Tara, Carrie, Latoya, Anne, Kelly, Kelli with an I, Carolyn, and, Virginia, that’s ten. Olivia would be eleven.

I’ve enjoyed all of them, watching them one by one learn that their husbands didn’t have to be their only lovers. Most of them have openly cucked their husbands. But it doesn’t matter I get my satisfaction either way. Olivia looks like she’s going to be open about it. Ross is going to end as a knowing cuckold. If my folks knew, would they be proud of me or ashamed?

My folk's lifestyle has changed me. Better or worse, I don’t know. I do know I enjoy it. 

The stories were a lot more obvious to me. I helped Olivia understand a lot about the stories, I was able to explain the love and affection in some stories that were missing in others. The different kinds of humiliation Where the humiliation seeped outside their cuckold life. I could explain what it meant to both the wife and the husband. 

It helped that I regularly related it to Mom’s and my Dad’s relationship, and about some of the cuckolds, I’d met through my parents. I think it made her less nervous.

I made her think about what she wanted compared to what we could see Ross wanted. I decided we needed to go out for lunch later, so she could just think and listen to me.

Olivia

Rosie helped a lot by calming me down as we went through Ross’s e-mails, forum posts, and videos he’d watched. She’d related what her parent's experiences were and in some cases other cuckold couple’s experiences too.

Eating lunch, I asked Rosie where to go from here, what she thought she learned from what we found. Rosie started slowly, thinking, 

“Hmm, well, first off, I think you need to recognize, uh, that what people read, and get off on isn’t necessarily what they want in real life. Second, it's obvious that Ross fantasizes about being cuckolded. Here, I am remembering some couples Mom talked about. Where the husband started the cuckolding but later changed. The rush wasn’t enough to endure the jealousy and humiliation or the wife tried to take it where he didn’t want it to go. It can get really complicated and sometimes it’s ugly.

“I saw how lucky Mom was pretty quickly. She jumped in and seduced Dad into jumping with her. They both loved where they ended. Just the few years I lived at home after knowing, I saw how bad it can go, with other couples 

“Thirdly I guess, is be sure where you want to go and be sure that Ross will too. 

“First though, if you want me to help you, you should know a few things.” She looked at me, hard. “I’m not completely unbiased. Ah, I consider myself a cuckoldress helper. You’re not the first friend I’ve introduced to cuckolding, I seem to recognize potential cuckoldresses, married to latent cuckolds. Knowing I’ve helped create a new cuckold couple turns me on. Just listening to them as they tell me about the first time they cuck their husbands, the first time they feel their first lover's cock enter them, I come, just knowing about it, makes me come. I try to be impartial and so far I think I’ve been successful.”

“So far, we know you, Olivia might be interested and that Ross likes to fantasize about cuckolding. The most common problem I worry about is if you and Ross try it, but one of you doesn't like it. If you start, and you enjoy the sex, you won’t be able to stop. Sooo, if you're unsure, now or later, tell me.”

I thought for a minute then, “Rosie, you gave me a lot to think about, and I will. When Ross gets home, I intend to have the computer open to Firefox and talk to him about it. Umm…umm would you … be willing…could you help by talking to us. Could you if I asked, later?”

Rosie looked at me, “ It would be the good, the bad, and the ugly. As best as I can. OK? Maybe just a bit of tantalizing stuff.”

I nodded, stood, and kissed her. I was heading home, and getting ready for one of the most critical talks of our marriage

I went and started the computer, Firefox, and then some of his files. I had opened a large collection of videos, his forum posts, articles on cuckolding, and stories, waiting for him.

Ross called at about five, saying they would stop and get a bite, to expect them after seven but before eight. 

OK, I had a couple of hours to do this so it didn’t destroy our marriage. First, what not to say? Then what to say 

Don’t: accuse him, make fun of him, humiliate him, not yet at least, leave that for later.

Ask him: Does he want to be cuckolded IRL? What kind does he want, in front of him, a motel-hotel, him seeing or waiting? Does he want to participate? Does he picture a dominant bull or friendly sex partners or one-offs? And what are some absolute turn-offs for him?

I texted Rosie. Can you talk?

When she called I went through my lists asking if I was making a mistake. She answered that what I was outlining was close to Betty, her mom. wished she had done.

The other suggestion was to read some articles about cuckolding. Not erotic but more clinical. Have them open but one of the videos with the cuckold watching the couple fucking paused, on top of the rest. Use what you read as part of the discussion. And don’t try to resolve it in one session.

Shit, what could have been hot sexy foreplay to fabulous sex is ending as a TALK. Hell, just like the marriage manuals suggest.

When Ross got home, Sam just dropped him off and I called him into the office. I had a cuckold video paused with the cuckold holding the other guy’s cock with a clear shot of the other guy's cock entering the woman’s pussy.

I swiveled my chair to face him and stayed silent and as I waited, I could see him gradually realizing what I was looking at.

He started with, “Missed you today, um…um. What are…uh looking…SHIT.

“You tell me what I am looking at.” I scrolled the windows.

This wasn’t going the way I wanted so I. restarted. “Look Ross, I don’t want to play games. I’ve seen this cuckold stuff you’ve been hiding. I’ve read some stuff you've been reading, I’ve seen some of the v-videos, and read some of  your posts on the forums you visit.”

He started to say something but I raised my hand and continued, “I guess my question is this just something you get off on? Or is it something you want in real life?

“I spent some time talking to a friend, um, she knows something about um, cuckolding. She’s single and hasn’t done it, as far as I know anyway. Her parents did and she knew about, learned about it, when she started college. She’s thought about it and her mom, her dad too, told her about it.

“Anyway, just tell me. Tell me the truth.” I half-laughed. “Now that I know, what else should I know.” There, that was closer to what I wanted. Continuing, “Are you relieved I know, ashamed I know, embarrassed, what? I love you, Ross. This is something you need to share with me. Share it with me, please.”

This wasn’t the end of it. Ross had a lot of conflicting emotions. Yes, I want to be cuckolded, I want to see you fucked, I want you to come home fucked, and I can’t stand thinking about any of I and I don’t want anything to do with it. Rosie was right, one conversation wasn’t enough

Rosie and I had several private lunches until I asked her again if she was willing to talk to Ross. I did tell her I told him about her parents. We eventually decided to meet at the park Rosie and I met at.

She told him that it was unlikely I would be willing to quit if we started. Even if I did quit, he would always see me being fucked by someone else. No matter what happened, he would always wonder if I really enjoyed sex with him. For most cuckolds, the angst of wondering was part of the attraction. 

She did everything to make it as real as possible. But in private, she continued to share with me that she wanted me to cuckold him. She enjoyed sharing the sense of power when her mother cucked her dad, and the power the other wives shared when they cucked their husbands. Despite what it looked like, she was trying to ring Pavlov's bell in front of a potential cuckold. If Ross isn’t one then it wouldn’t work. 

She also told me, “If, he says yes, do it. Make him watch it. Make him smell the sex. Make him help. Whether it's shaving your pussy, dressing you at home, undressing you in the hotel room in front of the guy, or making him place his cock in your pussy and watch the first new cock entering you, make him help. It changes it from 'you did this,' to 'I did this.'

He may resist but insist if you want to cuckold Ross. While the two of you are fucking make him picture a different man in bed with you: a different cock entering your pussy, a different cock releasing cum inside you. Have him picture the sense of bliss on your face as he collapses on you.

“I think, I’m sure he wants to be cuckolded, he wants to be your cuckold. He wants you to have lovers fuck you, he wants cocks to cum inside you. You are sitting here almost coming just picturing it. I’ve quit being an impartial friend. You want it, he wants it. Make him give it to you. “

That night, Ross and I were fucking, me riding his cock and I was saying,” Fuck me before Ross gets home, hurry, fuck me. I want to feel your cock cum in me. When Ross gets home you’ve got to be gone. I’ll give him sloppy seconds. Just cum in me“ I squeezed my pelvic muscles and Ross came. And I collapsed on top of him. “You’ve got to leave before Ross gets here.“ I kissed him and rubbed my hands on him

The next night as we were in bed together I said, ”Just think when you tell me to cuckold you, you will be able to watch me undress for someone else. You’ll see him watch me undress. You can see him kiss me, kiss my tits, and watch me react to my tits being kissed and sucked.

Watch him pull me under him, and place his cock at my entrance. The very first cock since yours first penetrated me. You can watch as his cock slowly disappears inside, maybe I’ll make you put his cock in my pussy so you'll be cucking yourself.

I want you to just picture me, my eyes closed, enjoying the sensation of his cock slowly penetrating my pussy. You can enjoy watching me react. Oh god, my pussy wants him, my pussy wants him, it needs him. Let's go get him. Tell me I can get his cock.”

As I said this I pulled Ross over me. “I want you to put his cock in me, please.” 

I grabbed his cock and placed him just right. “Tell him to fuck me.” 

Ross shouted, “Put your cock in her. Fuck her. Fuck her. Cuckold me, cum in her, knock her up. Shit, cuckold me.” While he was saying this and a lot more he tried to fuck me into next week. He was pounding me until he screamed, “Cum in her pussy make me her cuckold.” He came, held himself off me, rigid, and then rolled off, 

He held me and he could barely talk. “Olivia, w-when I heard what I just said, god, we’re, I’m going to have to try it. I hope it works out for both of us. Listening to Rosie, it's often a one-way street. If I can’t t-take it, you may n-not be willing, able to quit.“

We left it at that. I talked to Rosie and we met after work to calm me down and think. First I told her about the sex last night and how Ross had reacted and what he said during the sex.

“He scared me when he talked about maybe not being able to cope.“

Rosie answered, “I guess it's possible, but, remember I don’t think Ross is going to be able to not do it. It's been an obsession looking at cuckold stuff. For some people, it's the feeling of power, for others it seems to be that once their husband has allowed another man in his place, he should share, he should be forced to share, that part is up to you.

As we talked I could feel my tension leave. Ross and I would decide. Not me and Rosie. Ross and Olivia.

That night during dinner, I started asking Ross about what he pictured in his cuckold fantasies. I started by asking about the scenarios I knew about

Generally, I asked about the helping cuckold, or did he picture being there watching? Did he see himself participating or even not being there?

I just wanted to feel him out. Ambivalent was the best word I could describe what he said. He was saying. I want to see you being fucked. I want to be kissing you while I want to be imagining what the two of you are doing. A stranger. One of our friends.”

 It was such a mish-mash that I couldn't make any sense of it. I ended it by saying, ”I get it. You don't know and that’s fine. That means I get to decide. I will decide by the end of next week. You’ll know by then what I decided. Don’t ask me about it. When I‘m ready, I’ll tell you.

I went in and watched TV, kind of. Mostly though, I was trying to decide if I. wanted Ross’s first cuckolding should be in front of him. I decided I wanted him to see it like Rosie said, as it happened. I wanted him to see my expressions, hear me, smell the sex, and see the guy cum inside me.

Later I realized I wanted to make it as tough on him as possible. Maybe I wanted to see him cry. I know I wanted him to feel it, his first time as my cuckold. I guess I wasn’t very nice.

I didn't feel the way Rosie’s Mom felt. I resented being put in this spot.

I got ready and went to bed and to sleep before Ross came up. At least that’s what Ross thought. While pretending to sleep I was making decisions. I wanted it to be someone I knew. I wanted it here on our bed. I wanted him to stay all night. I wanted Ross there at first. During the first fuck. Then I wanted him to leave us but still hear us fucking.

There was Alan, an out-of-town salesman that came by on Fridays. I could invite him to go out to dinner Friday. He would be perfect. He has been flirting, he’s asked me out a couple of times. He’s good-looking, perfect for Ross’s first time, perfect for my first time. I relaxed and fell asleep.

At breakfast, I mentioned that I had forgotten to tell him that I had invited Alan out for dinner a couple of weeks ago. We ate and cleaned up, and headed to work On the way I called Rosie, 

I know not while driving, I pulled over first.

I told her about Ross’s indecision and what I had decided.

At work, I got ahold of Alan on the phone and invited him for dinner with Ross and me. I also mentioned that if he wanted, he could stay the night, I made the reservation for 7:00 at Fabians, one of my favorites. At lunch, there were six of us so Rosie and I didn’t get a chance to talk except for a few words while going back to work.

At home, we both avoided talking about cuckolding or what I intended. This lasted through Friday morning when I texted Ross “It's happening tonight, with Alan. Just that, I added nothing else. I had a hard time concentrating until l left for home at five.

Ross was already there and I saw him walking back and forth in the living room. I kissed him, then asked if he wanted to freshen up my shaved pussy. I had shaved a couple of days before and he hadn’t been allowed to see it since. He stuttered, “ Sh-shaved pussy?”

“Let's go up so I can shower, and you can tidy up my pussy." I started my shower, cleaned myself including my pussy, and handed Ross my razor. “Be careful, no nicks, and make it smooth for Alan. He was trembling I almost took the razor and did it myself. When he finished I told him to shower and get dressed. We needed to leave by 6:30.

Ross drove on the way and I tried to amp him up. Talking about how I was looking forward to tonight. I also outlined how it was going to go tonight. It was going to happen in our bedroom, He was going to be sitting in a chair. He wasn’t allowed to say anything. When Alan and I were through he was to go to the guest room. He was to stay there with the door open.

I was inviting Alan to stay the night and I wanted him to hear what was happening. I added that because I hadn’t made it clear to Alan, I wanted him to use the restroom for at least five minutes, so I could tell Alan. I also told him to relax, Alan won't know what is going to happen until after dinner. Then I added, “I’m going home with Alan.”

We got there about ten minutes early so I gave my name at the front and was given a five-minute wait. We went to the bar and Alan was waiting .and I introduced them. When we sat down, Alan was comfortable and Ross was tense. I was enjoying Ross’s nerves. He knew his first cuckolding was just a couple of hours away and getting closer. Minute by minute. 

I relaxed and acted as the host by helping Alan order what I knew was good. I ordered wine and I toasted,  “To good friends and good times.” And smiled at Alan and then at Ross. I was loving having Ross understand the subtext while Alan did not.

I tried to keep Ross in the conversation but with difficulty. I learned where Alan went to college and some work history. I shared that Ross and I met at Michigan State and got married a year after graduation. No kids. All the usual. We ordered dessert and over dessert, Ross excused himself to the bathroom. 

When he left I looked at Alan and said, “ I hope you can stay over tonight.” And I waited for him to answer. YES, He nodded a little hesitantly.

 I continued,” Ok there are some things I need to share. I really want you to stay because Ross and I are starting a cuckold marriage. He wants to see me with other men and I want you to be the first man to cuckold him.”

Alan thought a second and replied, “Ah, so. I was getting something. I wasn’t sure what. Ross seemed nervous. Are you asking me, without asking me, if am I willing to be your and his first? The answer is yes, but I do want him to tell me. Uh, how do I do it? Just ask if he wants me to cuckold him. Ask if he wants me to sleep with you. Ask if he wants me to fuck you.”

“Ask him when he gets back. Make it clear what you’re asking. Just ask Ross about, um…um, fucking me. Use the word fuck and Olivia, I think. Like this Ross do you want me to fuck Olivia?

“God Alan, I am going to enjoy tonite. I am inviting Ross in the room for the first um … fuck. Then he is going to the guest bedroom but I want him to listen. How late Saturday can you stay? Um, decide whenever, whatever you want to. 

When I saw Ross coming back, I pulled Alan up and kissed him. I looked at Alan and he hesitated then said, “Ross, Olivia told me what’s going on here. Um Ross I need you to answer, do you want me to fuck Olivia tonight, cuckold you?”

Ross tensed and then he answered, “I know what’s happening. You’re going to make me a c-cuckold tonight. You’re going to f-fuck Olivia tonight. Uh, so yes I want you to do it.”

Walking out, holding Alan’s hand, I told Ross that we would meet him at the house and not to worry if we were a little behind you. I smiled at Ross and then at Alan. 

I could see the pain, humiliation on Ross’s face, and his hands trembling as he held the key to our car. When Alan got me to his car and opened the door for me, I turned and put my arms around his neck and started kissing him. I felt his hands go to my breasts, holding them and caressing the tips. The headlights from our car splashed over me and I knew Ross could see everything. I stood there enjoying the kisses and his hands fondling my breasts.

I moved my hands from his neck to his shoulders and gave him an open-mouth kiss with my tongue exploring his mouth and lips. 

“Let’s leave. Um … I um, have a question for you. I’ll let you decide. I was… wondering if we should go inside my home and let you undress me there, or um, undress me before we get there and walk in like that. What would you prefer? Either way, we can sit on the sofa and have Ross get us some wine. Or? Ross serving me a drink already naked or serving us dressed with him knowing he is going to go upstairs and watch you undress me there.”

Alan started driving slowly and then pulled over. “I think, I think what I would like is to surprise him. He is expecting us to go in dressed. How about naked, naked from the car to the front door? Shoes and nylons on? Would you go in with shoes and nylons on and panties almost torn off?”

I could feel my pussy wetting, and I answered. “Yes, yes, torn enough I have to hold them on. Your shirt is off, belt loose. Lipstick kisses on your chest. I want to come in with marks on my tits. There’s a park we can do this. 

 I directed him to the park and as I undressed Alan, he undressed me, unzipped my dress and I got out so I could get out of the dress. I got back in and put on a heavy layer of lipstick and started kissing his chest. He got rid of my bra and started kissing my tits. Sucking and biting them, leaving marks. This felt so, just so! I loved it. I was kissing him rubbing my lips over his face, leaving lipstick marks all over him.

His hands were exploring, gradually moving down till he was rubbing my pussy. At this, I asked him to mark me just above my pussy. When he was done he grabbed my panties and ripped them. I started caressing his chest moving down so I unbuckled his belt and unbuttoned his slacks and started searching for his cock.

 I finally realized we needed to get home, OR!

“Let’s get home now before it's too late.” I guided him to our house, We pulled into the drive and I checked for pedestrians and it was clear. I walked through the door in front of Ross. Naked, hair mussed up, Marks on my tits and one on my pussy. I had to hold my panties on. I smiled at Ross and came up to him with my arms open. I hugged him, kissed him, and whispered, “So far it’s going great. But I haven’t cuckolded you yet.” 

I turned and kissed Alan and said to Ross, ”Get Alan and me a glass of cognac. Uh, that’s two glasses.”

I led Alan to the sofa and we sat down. His arm was holding me and my hand caressing his chest. Alan was sitting there shirtless, with lipstick kisses on his chest and lipstick marks all over. It was obvious that his belt was undone and his pants unzipped.

 Ross looked shell-shocked but was able to carry over the two glasses of cognac. 

I took one and handed one to Alan.  So, there I was sitting in front of my husband, naked, with hickeys all over my tits, and sitting next to the guy that did it, practically naked. I took a sip of the cognac, stood up, and pulled Alan to the kitchen.

When we got there I started crying. “Alan, I’m sorry, I'm sorry for getting you into this. I can’t do this to Ross. I love him and he doesn't deserve this. I can’t do… “

Alan looked at me and smiled, “Olivia, I agreed, but I was getting uncomfortable, This isn’t the Olivia I know and like. I shouldn’t have said yes but I did. Anyway, how do we go forward? Sneak out the back, go in and apologize, what? I can forget any of this. It is a secret for just the three of us. When I come next week, I would like to keep coming, I would like to take you to lunch, and let me know how this ended. If you can. Your clothes, You can get them next week or I can get them and bring them in. Which would be best? “

Olivia continued crying but was able to say, “Thanks, Alan. I promised you a room but I don't think that’s still a good idea. Where shall I get you one?”

“I need to go to Ross. Let him know. Let him know how I … screwed this up.”

OK, Olivia, I'll just sneak out and you talk to Ross. Should I call in the morning or wait till next Friday? The room, no room, please.

“Friday, Alan.“And I almost quit crying.

 After Alan left, I walked back into the living room where Ross was standing, looking dazed. I walked up and hugged Ross then kissed him.

“I'm so sorry, Ross. This isn’t who I want to be. It started wrong and just escalated. I sent Alan away, I couldn’t continue this way. I love you and, um, I just couldn’t. This wasn’t what you wanted or what I wanted. I want it to be us with my lover, not my lover and me, with you alone. Does, d-does that make sense? Make any sense?” I waited, holding Ross. 

 Ross tried to respond but just stuttered, made noises, and ended up just standing there holding me.

I started pulling Ross into our bedroom saying, “I want you, I need you to make love, to fuck me. Whichever you want, need.“ And I started stripping him, then finished my nylons myself.

While holding his erection, while feeling his skin next to mine, I was thinking I love this, feeling Ross naked, but at the same time hoping he would still let me cuckold him. Even at the time, I realized that was crazy, one or the other, not both thoughts.

Still, I welcomed Ross kissing me. I was stroking his cock, pulling him over me when Ross took over. He moved down sucking my tits, making new bites, new marks of Ross’s ownership. Slid down and sucked my stomach marking me there, then flipped me over. Then he started punishing my ass. Slaps to one cheek then the other. He had never even tried this and I was so stunned that I let him do it. I even raised my ass.

By the time he quit, my ass cheeks were burning and when he turned me back over it hurt like Hell. With no pause, his cock was positioned and slammed into me. Ross was fucking me! God, he was rough. While his cock was pounding me his hands were mauling my tits. Mauling them. My ass hurt, my tits hurt, and my pussy was starting to hurt from the pounding.

All I could think was, “God, I Am Being Fucked.” The third time I thought about it, I felt it starting. The spasm, the clenching of my vaginal muscles, my arching into Ross’s cock. It was wonderful, I was slowly coming down, even enjoying my pain, and then I felt Ross cum in my pussy. I collapsed and Ross, Ross’s full weight was on me.

He turned me so I was facing away, put one hand on my tits, the other on pussy and I knew he was feeling his cum oozing out. We lay there with my ass wiggling against his cock. I closed my eyes enjoying the sensations, the pain, and Ross holding me. I didn’t even try to say something and as I felt Ross relaxing, his breath slowing. I let myself slip into sleep.

I woke up feeling Ross trying to get up without waking me. I heard him pee and I sat waiting on the edge of the bed so I could kiss him. After finishing. I used the bathroom and came back to bed. “Do you um,..want to talk now or wait till breakfast?”

 Ross’s response was just a, “Later, please.” Then wrapped his arms around me and pulled me closer. 

When I woke again I started coffee, showered, dressed, and woke up Ross. I was watching the morning news when Ross came into the living room.  I started, “Is it later enough?“ as I walked toward him. I hugged and kissed him and said. “ This whole thing went wrong. I think I resented your not telling me what you wanted. I guess I wanted, shit, I wanted to make you regret not telling me. That’s so not what I want. 

“I, um, I remember Rosie talking about her mother talking about couples where the wife um, seemed to dislike her cuckold—her husband. There was little to zero affection from the wife. That was crossing my mind when I st-stopped everything. If this is, or was. something you needed, wanted, uh, needed I d-didn't want us to end like that. Ross, I love you. I like you and I want it to stay that way.”

I apologized again and we eventually got to the point where we kissed and made up by making love right there on the sofa. I ended by saying, “This is the last word. If you still need it, think hard, and know what you want. Then bring it up like it’s the first time.”

ROSIE

When I got the phone call from Olivia about her aborted cuckolding attempt I wasn’t completely surprised. I’d gotten the impression that she’d started being upset with Ross. I wanted some private time with her so we met at our park bench with coffee. Olivia didn’t want to share everything that happened, but I got most of it. I sat there absorbing it then started, “It looks to me that you wanted to get back at Ross, even before you contacted Alan, right?’

Olivia was looking ashamed, but replied, “Exactly, but when it got down to it I remembered what you’d said about the wives that seemed to actually dislike their cuckolds, their husbands. That wasn’t what I wanted us to be like. I guess I didn’t want it enough so I couldn’t go on.”

I looked at her and smiled and said, “Um, this is the first time I’ve run into someone that stopped it, midway. That must have been embarrassing.”

Olivia replied, “It wasn’t as embarrassing as realizing what I was doing to Ross. Between the two, stopping it was less embarrassing, by far. I don’t know…“ and she stopped.

“Well, I have to give you credit for being willing to stop it when you did.” I hesitated then continued, “Do you think Ross realizes what that means, that you love him? Uh, where did you leave it?”

Olivia thought before answering, “I guess uh, I told him to think about it. If he wants to try again, let me know. Be sure what he wants though. I’m not sure what he’s going to do after that debacle.”

I answered, “What I think, is making him decide again, was the best thing you could do. It reaffirms that it’s what he wants. You’re not doing it to him, you’re doing it for him. From what I’ve seen, he’s going to still want it. Be ready with an answer when he does. Let me know when he wants to finish your cuckolding him.”

I think this is going to end the way both of them want it to, I’m sure that Olivia’s going to cuck Ross within the next two months, maybe in one month. I’m going to enjoy the whole process. Yum.

A month later, after a very nice session, Ross started, “I want to tell you something. If you um, go into the office uh, computer, you’ll find uh, Firefox. “Open the favorite list and go to the cuckold forum. Um, it’ll take you to um, my user. Look under My Posts. There is one I want, need you to read. Now if you can. Please.”

He was turning pale as he continued, ”After you read it take any time you need to think about it. When you are ready, all you have to do is say, ’Message to my lover.”

As I got up from the bed I was thinking if he decided he had changed his mind he would just ignore it or send a text that he had changed his mind, but, anyway, I would know in a few minutes. The computer was on but I had to turn on the monitor. Firefox was started, Cuckold Forum was opened, and a post called ‘message to my lover.’ was opened.

‘My dear Lover

‘There are some things I hid for a long time, too long, I think. We have enjoyed a lot of intimate times and I don’t want to change that. I enjoy everything we do together and I don’t want to change or risk any of that. I want and need to see you with a lover. I want to see you kissing someone, I want to see you naked with someone else. I want to see someone else’s cock entering you, see your expression as it happens. I want to see you come with s someone else’s cock. I want to see him come in you.

‘I want to be your cuckold. I also want to be your lover. I don't want to lose what we have, just add to it. Reading these forums, cuckold marriages can be like that, but a lot aren’t. As I am writing this, I am picturing myself on you holding your tits with my cock inside you, but at the same time, I’m picturing you naked with someone else holding your tits, fucking you. 

‘That’s what I want. If I can’t be your lover and watch you with other men. I want to be your lover. I want to be a cuckold that has his wife too. I am willing to help get you ready for your other lovers, I am willing for you to use our bed, and I’m willing to consider overnight and weekends away, after a time.

‘I am willing to enjoy watching your pleasure as long I still have you.

‘ Your lover and cuckoldwanabee.’

I sat there when I finished. it’s almost exactly what I wanted him to tell me. I dropped my robe and walked to our bedroom naked, saying, “Message to my lover.”

We had a lot of fun over the next few weeks while talking about it, planning it, and role-playing it. One of the most important questions I had for Ross was about humiliation. I knew that simply being cuckolded held a lot for most men.

The stories and forums made that clear. It also made clear that for a lot of cuckolds, if not most, humiliation was one of the turn-ons. How much did Ross want and how much would he tolerate? It took a lot of talking over a long time before I felt I was comfortable.

When I started being comfortable, I brought up my first lover. The first man to cuckold him. I wanted to enjoy cuckolding Ross. As I made clear to Ross, I didn’t want a stranger, I wanted Alan again. I still wanted to fuck Alan, I wanted to cuckold Ross for the first time with Alan. I knew that using Alan would feel humiliating for Ross but I wanted it to be Alan. Period.

I made it clear that it was going to be Alan that made him a cuckold. It was Alan that he would let fuck me. Alan saw the first attempt, he was going to be there for his first successful cuckolding. I could tell that he wanted someone else, almost anyone else. I insisted. There might have been a remnant of wanting to humiliate Ross even before having Alan's cock enter me. I'm still not sure.

It took several days before Ross agreed. The date was set for Friday in ten days. That gave me time to talk to Alan again. I had been keeping him up to date over the last few weeks and had let him know I wanted him to be our first.

I also made Ross take me shopping for my first cuckoldress outfit. New dress, easy to take off, new lingerie, new everything. I made Ross shave me a week before then Friday morning. I made sure I gave him lots of loving sex, telling him I loved him. I loved him and I loved him for letting Alan fuck me.

No sex on the day, but lots of affection. Ross shaved me, put lotion on my skin, and especially on my pussy. This time I had Alan meet at our house and we took our car to the restaurant. I played it low-key until we got home. As we walked in the door I gave a huge passionate kiss to Ross while murmuring in his ear, “I love you, Ross. When today is over you’ll be my cuckold. Maybe twice. Thank you, dear.”

I kissed Alan, much like the one I’d given Ross, then said to both of them, “Let's go upstairs.” I gave them both a kiss and led them up. Ross and I had planned the first part and so Ross led me to the bed unzipped my dress and carefully hung it up. He took my nylons off and stood back. I walked to Alan and knelt and removed his shoes and carefully unbuttoned his shirt and set it aside. I unzipped his pants, got him out of them, and placed them over a chair.

As I kissed him I pressed my tits to his chest my hands caressing his shoulders and chest and pulled back the bed covers. We started playing with each other, Alan with my tits and one hand down to my pussy. I was rubbing his back and chest, touching his cock. I could see Ross tense, he knew he had one last task before he sat down. I was luxuriating feeling the sensations of my tits, pussy, and ass being fondled by the man who was going to cuckold Ross, my husband. 

Just the thought, aroused me. Ross was going to willingly, willingly let Alan fuck me. I said to Alan, “Now.” Alan got between my legs, his cock ready and I held him back. Ross had one last task, a task that Ross agreed to do, that would make him a cuckold for the very first time. Ross reached down and placed Alan's cock in me as he pushed forward until his cock disappeared inside my pussy. I sighed in satisfaction as I felt a new cock in me.  And with the thought that Ross, Ross had been the one that ultimately cuckolded himself. He’d put Alan's cock in me.

Two more thrusts and I came, the whole process was so exciting. I was delirious with the sensation of Alan’s cock in my pussy, his hands squeezing my tits, his weight on me, and my nails in his ass. I sensed Ross moving away. All I could see was Alan over me, fucking me. I came again. As I came, I could feel his tensing spasm and see his grimace as his first load of cum was deposited in my pussy. His first load, my first load, and Ross’s first load as my cuckold.

I have vague memories of looking at Ross and seeing his cum all over his clothes. I do remember Alan fucked me twice more, and Ross fucking me at the end. 

When I woke there were the three of us in the bed with me in the middle. I was holding Ross's cock and Alan was rubbing my tits. 

I lay there basking in the memories, all of them. The main one was Ross was my cuckold. My loving husband cuckold. My husband and I loved him. Oh, and I intended to do it again.

Rosie

Olivia shared a lot of what happened after her aborted first attempt to cuckold Ross. I got as much pleasure and excitement from Olivia's transition from wife to a hot wife as I’d hoped for. Even though I delight in watching the transition, I don’t need to go looking for it. It just happens.

Oh, I’m getting vibrations from my friend Lindsey. We’ll see what happens.