How did ladies feel after their first cuckolding experience
I don’t remember if I’ve written about the first time I cuckolded my husband, Tom. If I’m repeating myself, please move on to near the bottom where I answer the actual question above. I’m writing the whole thing (maybe again?) because I think it will give help give context to the answer.
I was always the flirty type, never tried to hide it, and I still flirted with guys even after I was married because it was fun and I enjoyed it. My husband knew it, and only later did I find out he was actually fine with it. I never cheated though, but I admit I had a lot of fantasies. After around two years of marriage, one day Tom and I were at the beach and we stopped to get some drinks from this little stand. We sat down and before long this guy, Dan, walked over and sat down at the stool next to mine. He was wearing only swim briefs, and his bulge was so huge (and still soft at that) I couldn’t take my eyes off his it. Tom, who I didn’t think was watching that close, told me later that he thought I was going to “go catatonic” from lust. That’s one of his favorite things to say now.
Other than to say “Hi”, I’d never talked to Dan before, but I’d seen him around, and I knew a little about him from from a female acquaintance who knew his story. He was in his mid to late twenties (around my age at the time), recently divorced, and starting to date again. He spent a lot of time at the beach, and had an apartment not far from there.
Dan and I started talking and flirting with each other. If he realized I was with Tom, it didn’t matter to him. We exchanged phone numbers. I’d done this with other guys, and always gave them a fake phone number myself, but I always kept their numbers (I never called one of them, but just the fact that I kept them tells me I probably couldn’t have remained monogamous much longer).
That night, Tom and I made love, and I tried to get into it, but as was almost always the case, I was faking it. I admit I was thinking about Dan from the beach. After Tom ejaculated, we had some pillow talk. He said, “I know I don’t satisfy you.” I said, “Don’t worry about it, you’re fine.” He said, “I want you to be honest. Have I ever made you come?” I told him I wasn’t comfortable with this conversation and to forget it. He kept asking though, and I finally admitted that no, he never had. Sometimes I’d get a small orgasm when he’d go down on me, but nothing like the kind I’d gotten from other, bigger, more skilled guys. I was angry with him for making me admit it, for making me hurt him. He said he wasn’t hurt though, and that he really needed me to keep being honest. He said he’d found my vibrators (I thought I had them well hidden). He said, “That’s the only way you can come, isn’t it?” I admitted it. I said, “Look, Tom, I can only fully orgasm vaginally, that’s not your fault, but it’s not mine either.” He said, “I know honey, I’m not blaming you, I love you. If you love somebody, you want them to be happy, to have the pleasure they need.” I can’t remember everything else we said, but he ended with, “I mean, if you strayed once in a while, I could live with that, as long as you still came home to me.” I couldn’t believe what I was hearing. I knew he liked hearing about my past encounters, but I saw it as just some added spice that helped him (and me) get off. When he said he was fine with it if I actually “strayed” I got worried. I thought all kinds of things, like he’s saying this because he’s got some girl himself, and if I sleep around, that will give him permission to do it. I came right out and asked him if there was someone else, and he said no, he didn’t want anyone else, ever. He just wanted me to be happy. I actually sort of believed him. I was pretty sure he was being honest. I still thought it was crazy and wrongheaded though, and I told him we were finished with this conversation.
In the following few days, he kept talking to me about it anyway. I didn’t say much, just listened, trying to figure him out. I finally felt like I could be more honest, and I told him that I sometimes kept the phone numbers that guys gave me, but that I’d never used them. He asked if I’d kept the beach guy’s number. I said yes, and Tom promised me he wouldn’t be mad or make me pay for it later if I called this guy. I felt really confused. On the one hand, I liked the idea of a traditional, monogamous marriage. On the other, I was desperate for sexual satisfaction, and I knew I had been fooling myself thinking that I could hold out forever. I don’t know even today whether it was Tom or my own desires that finally convinced me, but I made the call.