I am going to begin with my marriage to Ann. I meet Ann at Spokane Falls Community College. I asked her out on a first date in early February and I proposed marriage in mid-March. If that seems quick it is helpful to note that I lost my virginity just a few night before. Yes, I was eighteen years old and still a virgin and yes I proposed marriage to the first woman to spread her legs for me and take my dick.
While she did not say "yes' that first time, a month later when I proposed again, she did say yes. I did not tell her at the time that I was a crossdresser. It would be another year plus before we were to marry and during this time it was not uncommon for me to ask her out, take her to a movie, fuck her on the way home and then as I was making the drive home stopping by a Goodwill box to check it out for any good clothes. Not ucommonly I would find a secluded spot and change into a dress and do my makeup at a gas station I had found that kept their restroom unlocked.
Should I have told her the truth? Unquestionably. But I did not. So unbeknowst to her Ann married a man who had real issues with his gender identity. When I watch this video, I can truly see myself as him and Ann as her. (If you would like to see more in this series, they are all at The Cuckold, a playlist I have built on YouTube.)
Ann was a bit of a bitch and she would have been prefect for the role of Jen in this video. Would it have bothered me to know that she would be going out and fucking other men? Yes it would have. But at the same time, I would have been envious of her. And when Jen is talking about his peepee, it could easily be Ann talking about my cock. Below is a video of a husband destined to be a cuckold.
Love the videos.
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