[First Time] Dilemma

[SandiG]

Jack’s sexual desires were very different from mine from the start, but I went along with the things he’d ask me to do. Lots of things. I’d never have done any of them myself.

Intercourse with others isn’t one of those things. Just about everything else is.

Jack would get really excited about what we’d do and that helped me to accept it all. I’m not complaining. I enjoy doing what we do and it really makes our sex life even more pleasurable.

One night, Jack was out late. I put on some music and had a couple of glasses of wine. The doorbell rang. It was our next door neighbor, Joe. He was always flirting with me and I flirted back as well. Jack already knew and never discouraged it. He’d get home and come over to visit before heading to his wife.

I invited Joe in and we talked for a while. After the wine I was really feeling it, so I excused myself and went upstairs. I took off all my clothes and put on my long robe and went downstairs. Maybe he’d think I was getting ready for bed.

We talked and a song came on and I asked him to dance with me. He got right up. Slow dance. As we danced, I loosened the tie and let my robe open to show him I was nude. He immediately started kissing me, touching and fondling every intimate part of me he could get his hands on or in.

He was hard very fast and I fondled his cock through his pants. He unzipped and I reached in and pulled out his cock. We continued kissing, groping and dancing as I stroked him. Pretty quickly he came and I had cum all over my belly running down. There was so much cum that I just took off my robe. Even with what we had been doing, I think he was surprised that I was now completely nude. I told him to stay there and I went for a towel.

I came back and started wiping his cock dry. I got a wet cloth and cleaned off his pants because I was sure his wife would be wondering why he had dried cum on the outside of his pants. I purposely left his cum on me so he could see it running down to my vulva. When I finished cleaning him, I cleaned myself. I was already so wet and excited that I decided to stay nude the rest of the time. It was getting late so I told him he’d better get home before he got in trouble. There was more kissing and fondling at the door, so I made him wash his hands before he left.

I told Jack everything that happened and he was so turned on, we got to it right there. He wanted to hear it all as we did it.

Jack wanted more. He wanted me nude next time Joe came over and started hiding and watching us play. This always ended in great sex for us. Foreplay with one guy and finishing with us.

Intercourse was still something just for us, but I had a fantasy I had been thinking about trying. So I lubed myself up ahead before Joe ever got there. After we were playing and he was sucking my tits while I was sitting on his lap I reached back, grabbed his cock and sat on it.

I don’t think he realized at first that when he felt me pushing down and his cock was going inside me that he was going up my ass. I slowly pumped for a while then faster until he came. I didn’t cum, but I was soaking wet from the excitement.

This has happened more than a few times since. I never told Jack this one and I know that soon he’s going to watch us again, so I’ve got a problem.

Do I tell him what we’ve done anal and that we have done it several times and that he’s cum inside of me? I really enjoy it, and I’d really like to look at Jack while he’s watching watching Joe’s cock going in and out of my ass. I always try to make eye contact with Jack while I’m playing. But I really don’t know if that would be a good or really bad thing to tell him. I should have talked to him first but I didn’t.

I’m thinking I could suggest it to Jack and see if he likes it. But if he doesn’t it will create a problem next time Jack is watching and Joe wants me to sit on him. It’s not like I can hide his cock going up my ass and me pumping.

[SandiG]

Originally Posted by SyFoster

So was your husband Jack watching the times you put Joe’s cock in your ass? If so, how did he not see that Joe was inside of you, and also came inside of you?

Either way, yes, tell your husband that you’ve let Joe fuck your ass multiple times. From the way you have described your husband, I really don’t think he’ll be upset. And even if he is, he really has no ground to stand on.

No, he wasn’t there, and that’s why I’m struggling. Next time when Jack IS there, I’m not sure what will happen because now we’ve been doing anal every time. It’s complicated. Jack isn’t always there watching, but during sex I talk about whatever experience I’ve had.

When we first decided to be more sexually adventurous we agreed on limits and other things. We both agreed that vaginal intercourse would be just between us.

Anal wasn’t discussed at all. I don’t know why not, neither of us thought of it at the time.

Outside of the limits we decided on, Jack trusts me with doing things on my own. I’m pretty sensible on what I can do and shouldn’t do. He’s been nothing but happy with hearing about new things I’ve done.

Because we never talked about it and we both enjoy anal, I started thinking that Jack would get very excited seeing me enjoying anal with another guy. Joe and I were already playing and Jack had watched us, so it would be easy to make happen. That night I’d go through every detail with Jack.

It felt so good, but after he came I just sat there for a minute then started to feel guilty, like I had really crossed a line. He’s had his fingers in me, but it’s still not the same as having his cock inside me and cumming. I enjoyed it. A lot. But after I felt so guilty, I couldn’t bring myself to telling Jack.

I felt guilty enough not to tell Jack, but the next time I found myself wanting it again. And again.

I’m a mess right now because I really want Jack in on this, but I really don’t know what to do. You say to tell him, but I don’t know what his reaction will be. If he likes what he hears I’ll have Joe in me in ten minutes with Jack watching.

I’m afraid it will mess everything up if I tell him and he doesn’t like what he hears. What we do works well for us. We have a great sex life, are very happy, love each other and I don’t want to start adding negative things and bad feelings to it. This is too good to mess up.

As I’m trying to think of a way to say it, I just got this idea. Next time we have sex, I’ll do exactly what I did with Joe. I’ll sit on his cock and as we are talking I’ll say “I’m surprised you’ve never asked to watch me doing this.” That way I can bring it up and see where he goes with it.

If Jack suggests it, we’re set. If he doesn’t want to do it, I’ll have to think of an excuse to stop. We’ll see.