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  1. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Hey guys! I just wanted to let you all know that she definitely got knocked up by James, and we're both very happy and excited about it!
  2. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Hey guys, I never updated here. Sorry about that. So basically: I moved into a small guest house on the property and she moved into his bedroom, for the week leading up to our wedding. We got married! That night he fucked her and came in her, I fucked her afterwards but she made me pull out. He...
  3. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Small update: We're getting married at the end of the month, and yesterday she asked me if I would wear a chastity cage until then. I would have liked to ease into chastity play, but I'm going to do two weeks straight!
  4. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    We had a nice romantic picnic together today. We discussed our wedding plans and we both agreed that this house and land was nicer than we could afford, and so we agreed to get married here before we leave in September. James agreed and now we're in a mad dash to get everything planned before...
  5. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    No, but I'll ask!Small update: I was out in the hot summer sun mowing the lawn and they were fucking with the window open. I had to listen to them the whole time. Pretty humiliating!
  6. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Well it's out in the open now! So I had been hard at work for a while and I went looking for her. I peeked out a window and saw her sucking him off. They were by the pool, and she was on her knees blowing him. That thing was huge, I couldn't believe she could even fit it in her mouth. Of course...
  7. CuckArtist

    Thank you!

    Thank you!
  8. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Just a couple of small updates! We were in the kitchen and he got out of the pool and we could see his huge cock outlined in his wet bathing trunks. She said "So that's what a cock is supposed to look like." She laughed it off and kissed me, and said she was only teasing.Then a few days ago...
  9. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    So I didn’t post an update because I didn’t really have anything to say. I stayed in our room working when they got home, waiting for her to come in. She finally did after a shower. I asked her about the boat trip, but she didn’t have much to say. She told me being out on a boat isn’t very...
  10. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Hi Custer! You are right that this may be more dangerous than I think, but I'm banking heavily on us moving away in September, and the fact that James isn't one for settling down. So I think this may be the perfect no strings attached situation.So, a little update. Last night she shaved her...
  11. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Things are looking good. I checked the bag she was packing and there's a very slutty swimsuit in it! I also noticed she's bringing a regular pair of panties, but I'm not sure that means anything.
  12. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Thanks for the encouragement! It's worth a shot, I just think my personality is too submissive for her sexual interests. She wants to be pinned to the bed and choked and I just don't think I'll ever have that i me!
  13. CuckArtist

    If It Hasn't Already Happened, It Will Tomorrow!

    Ok, so here’s what’s happening! My fiance and I have been dating since College orientation, and we just recently graduated. It has been four years of sexual frustration for her. All of her high school sexual experiences were with alpha male types, and here I am with a pencil-dick and a...
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