The turning point came when she told me she wanted to have another guy fuck her with his big cock while I licked her pussy. This is absolutely true. It just came out of the blue and I was really startled. We were in the middle of foreplay at the time and she was in one of those sexual highs where you’re sort of involved with and aware of the other person, but your mind is totally focused elsewhere.
Clearly, she was fantasizing and she just blurted it out. She was squeezing one breast and helping me finger her and was sort of panting and writhing. I just sort of chuckled while I worked her beautiful breasts and muff with my mouth, alternating and moving back and forth quickly. As she was nearing one of her peaks, I slid my cock inside her and quickly brought her to orgasm as I whispered and nibbled and sucked her ear. But I didn’t say anything about her little fantasy. I just let it go for the time being, but knew I’d bring it up later.
Gloria and I had been dating for six or seven months when her little fantasy slipped out and things had been going pretty well. I travel all the time but she has her own business to run. Hers is a small business with just a few contractors she employs while she does everything else. She makes good money but works very hard. She’s ambitious and assertive and, lucky for me, loves sex. She told me she needs it pretty much every day and it’s a great stress reliever. But I travel a lot. Can you see the conflict?
We had kissed rather passionately on our first date but did not have sex. That came (and so did we) on the next date two nights later. Then again two nights after that. And two nights after that. It’s funny that the two and two thing happened, but it just worked out that way. It was on our third night of sex, while we were engaged in foreplay, that she dropped the first of many bombs on me: she had a boyfriend!
They had been together for several years and were “in the process” of breaking up. She was done with him emotionally, but she was having a terrible time giving up the sex. They were just very good together in that area and she couldn’t quite let it go. Everything else was crap, but the sex: that was great! He was apparently well-endowed and knew exactly where and how she needed things done. He was a sexual convenience at this point. An alternative to masturbation.
Gloria is smart. She knows men and timing and knew me in particular well enough by then that she thought she could bring something up like that while in the middle of sex and could do it in a cute enough and elliptical enough way that I ended up aroused rather than angry. She took a chance, of course, but it worked. I wasn’t angry – heck, we had just started dating – and besides, that made me the bull!
They eventually officially broke up but continued to see each other platonically. What we worked out initially is that when I was in town, I got her full attention. We had a lot of fun with that because I was bossy as hell. She would be having coffee with her ex at a coffee shop or something and I would text her with a demand. She would just tell him that her new boyfriend wanted to have sex.
“Sorry, babe. Gotta go.”
She’d leave him with the bill and off she’d run. I loved it, she loved it, and her ex was miffed. Too bad for him. ‘Were they having sex?’ Probably, but she never said and I never asked. What mattered to me is that I did get her when I wanted her. And I wanted her a lot.
So then came that night I told you about at the beginning of the story. Like I said, it was just out of the blue – boom – she wants a threesome. Or maybe more accurately, she fantasizes about them. ‘Did she want to involve her ex or someone else?’ I travelled enough for work that she had plenty of opportunities.
We hadn’t talked about it since she blurted out her fantasy, but I thought about it all the time. She had, after all, done it before she met me. ‘Was it just a fantasy or did she really want to do it with me? If she did, could I do such a thing? Was she doing them on the side?’ Fantasy is one thing, but reality is another. I had to leave town a couple of days later and was scheduled to be going to Paris for work for a couple of weeks. During the trip, I found out much more about my new girlfriend.
I knew she had been married twice, but didn’t know much about those marriages. The first one had been what she called a starter marriage. At the time of their marriage, she had been a senior in college while her new husband had been in grad school. After the honeymoon, they returned to the same apartment with the same circle of friends and lovers they’d had before they got married. Gloria had been having sex with other people all the way up until the night before they got married.
“Really?” I had asked. “The night before your wedding?”
She laughed. Yes, she was a very naughty girl. And once they came back from the honeymoon she just picked up where she left off. She never told her hubby and never got caught. They divorced a couple of years later for other reasons, but something of a habit had formed: She got off on cheating.
It was five years or so before she got married again. She was having so much fun romping around with whomever she wanted that she didn’t know if she could marry. But for some reason, she did. With that guy, she struggled to stay monogamous for a year. By then she was starting to get some success in her business and they both were sort of going separate ways as they built careers.
She started fucking around again like any other addict. She suspected he did the same thing and she told me that that fact sort of turned her on. I was surprised to hear this, but she said she fantasized about it a lot. Then she’d go fuck one of her studs to get even with her husband even though she only suspected him of cheating!
That marriage only lasted a few years, then I met her half a dozen years later. And remember, we started dating and having sex while she was still another man’s girlfriend.
So on one of those late night phone calls, while I was in Paris and she was in Atlanta, I asked her if she knew what a cuckold was. She did not. I told her it’s a husband whose wife takes other lovers. She laughed and said she’d obviously had two of those (cuckolds).
“They’re fun,” she said, giggling.
I then sent her a link to an intelligent article on the topic. The writer talked about the psychology, thrills, angst, etc. and why both sexes find various aspects of it titillating. She didn’t read it while we were on the phone, but the next day I got a simple text while at work that read: “Intriguing. How do you know so much about this?”
I didn’t reply. Better to handle this one via voice when we could sync schedules. That evening she was unable to chat, so I found a few more resources. I sent her links to two really well done erotic stories featuring couples happily enjoying the cuckold lifestyle and then waited somewhat anxiously to see what she thought. First thing in the morning her text read: “OMG! So fucking hot!” Then a separate text: “Do you want me to tell you when I’ve had sex with someone else?”
That sort of took my breath away and I had to think about this one.
She replied right away: “I have a date.”
Which meant, of course, she was going to get laid tonight.
I should not have felt such uncertainty and anxiety about all of this, but I did. We were walking on shifting sand. I felt I couldn’t get my equilibrium and felt I was quickly losing control of things. The following night we finally got to talk. I had several things I wanted to discuss, but didn’t exactly know how to do it. ‘Who had she gone out with? What had they done? Did I really want to know? Were we headed for a threesome or a cuckold kind of thing or would I remain more of a bull (at least when I was in town) and then just choose to remain ignorant when gone?’ And on and on, but my conversations never go like I anticipate
Instead of asking any of those things, I eventually and very nervously asked her if I could trust her completely with my sexual fantasies. It would be a huge leap of faith for me. She assured me I could do so without any worries, so I took the leap and we talked about the cuckold articles and the stories and all that. Clearly, that stuff turned her on.
So I told her I wanted to send her some more stuff and that I’d have a special question for her in a day or two. She was pretty much giddy at the prospects. I then told her I didn’t know if I wanted to know what she was up to while I was gone. I couldn’t decide. I was quite nervous about the whole thing.
So then she said, “We are not married. We are not always even comfortable calling each other boyfriend and girlfriend. Here’s how we will look at things: You have a girlfriend and you must remain monogamous.”
Then she said nothing else as she waited for my reply. I held my breath for some seconds waiting to see what else she would say.
She said nothing, so I sort of chuckled and said, “Okay. And?”
“And I am a hot female business owner with no husband, no boyfriend and no restrictions.”
Unlike previous moods where she had been more frivolous, she sounded completely serious. She was totally setting a tone. It was pretty hot.
“Okay, boss.”
Then she laughed. “Ewww…” she said. “That was fun.”
We ended our conversation and I sent her links to some pictures and videos of wives fooling around. She doesn’t surf much porn, so I proceeded cautiously. Again, I did my best to send stuff that was both erotic and plausible for consenting adults without being too extreme.
Hours later her next text read: “You’re killing me. Had to get relief. Sure you don’t want details? I think I know what you want and have “friends” who can help. Wink. Wink. Hurry home!”
I told her I’d answer her later. That night we had a relationship-changing conversation. It took us a while to warm up the conversation about the kinky stuff, but she broke the ice by telling me she was surprised and turned on by what I had been sending her.
After some discussion about that and when I thought it was safe, I said, “I want you to use your imagination and create a fantasy for us. We’ll do whatever you want. We will make it a game.”
All I heard on the other end was silence. ‘Oh, fuck.’
“Are you there?” I asked.
“Yes,” she said. “Sorry. Just taking all that in.”
I started backpedalling because I thought I had somehow really screwed things up, but she stopped me.
“No,” she said. “Really, it’s okay. I was just thinking. I mean, we’ve already been acting out some of these fantasies whether you know it or not. But I -“
‘Whew…’ I let out a deep oh-shit kind of breath. Because now it was out there. This shit was real, not a fantasy. And then our conversation got interrupted by a call from a business colleague. I really had to take the call. It was late at night. That could only mean really good things or really bad things. I hung up with Gloria and attended to business.
Luckily for me, it was good news and, in fact, meant an early return home. I called Gloria back briefly to tell her the news and was happy to hear she sounded genuinely excited. She wanted to continue our talk and so did I, but I had to pack and get ready for more pressing demands. I assured her that she could not possibly make a mistake. We’d just make a game of things and see where they went. We finished our call all too quickly and I got to work packing and prepping for the real world.
I returned home tired but ridiculously horny and very anxious to see Gloria. She couldn’t meet me at the airport because she said she was with a client, but told me she’d meet me at my house after I got home and had showered. She finally showed up about ninety long minutes after I’d showered. I met her at the door wearing only a bathrobe. She was wearing high heels and a trench coat. Really.
“Sorry I’m so late,” she said. “My last meeting today was long and hard.” Her expression was sizzling.
When I brought her into the house I hugged her and kissed her and just freakin’ absorbed her body against mine for a few moments. Then she slowly opened her coat to reveal thigh high stockings, a very short skirt and a diaphanous top that was totally see through. Her dark areoles were clearly visible and her nipples tented the fabric. I was totally blown away. I just wanted to consume her.
I wondered about that last meeting. And the client.
She took me by the hand and went directly to the living room, shedding her coat along the way. Amazingly enough, she draped herself on the couch exactly the way my ex-wife used to, with her head on the armrest, one leg on the sofa and one down (now sans heels). Her skirt rode up her thighs to her hips and I saw she was not wearing panties. ‘Yum!’
I knelt down as calmly and coolly as I could and began kissing my way up her inner thighs, but could hardly wait to bury myself between her legs. When I did, I found she was so damn wet I couldn’t believe it. In fact, that’s exactly what I said.
To which she replied, “Well, of course, I’m wet.”
What I expected was a follow-on comment like, “I’ve been waiting for you,” or, “You’ve made me so wet.” But something in the way she said it made me pause ever so slightly, mental antenna all atwitter. I must’ve paused physically just enough for her to notice, because she calmly reached down and put both hands on my head, then pulled me slowly but positively into her crotch. Then she very deliberately began firmly and sort of rhythmically grinding her soaking pussy against my face. She was face fucking me.
“Remember our little game with others?” she asked. “It begins now. Or maybe I should say, ‘we started without you?'”
