The Man Who Took My 2nd And 3rd Virginities Attended My Wedding Years Later

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This is my confession of how I acted like a slut when I attended my sister’s wedding as her maid of honor. I hope my husband never finds out!

I’ve been feeling sort of “guilty” about this and think I’d feel better if I could tell somebody about it. But, of course, I can’t. No one knows about this except the guy that was there and maybe my sister and brother-in-law. I could never tell my husband about this!

Years ago, I was Maid of Honor at my sister’s wedding. The brother of my soon-to-be brother-in-law was the Best Man. After the wedding, during the reception, I “hooked up” with the Best Man. I wasn’t a virgin at the time, but wasn’t very sexually experienced at all. It was my first, and still only, “hook up.” Also, it had been over a year since I had had sex. Not being very sexually active, and pretty inexperienced, I wasn’t on the pill at the time. The Best Man was very good looking and we flirted. During the reception, after a few drinks, we flirted some more. We ended up slipping out of the reception and taking a ride in his car. We parked, made out for a while, and had sex in the back seat. It was really unlike me to do something like that. He was a near-stranger and here I was giving him a blow job (my first one ever) and having unprotected sex with him in the back seat of a car. It was pretty awkward both because I wasn’t very experienced and we were in the back seat of a car. I had taken my shoes, ‘hose, and panties off and pulled my dress up as high as I could so we wouldn’t make a mess all over it. I was lying on my back and he was on top. It started out a little uncomfortable because I hadn’t had sex in so long and he was fairly “large.” After a few minutes I loosened up and relaxed some and it started to feel good. He made me cum pretty quickly. He didn’t have a condom with him so we were doing it “bareback” (which really scared me). A few minutes after I came, I could tell he wanted to cum. I told him I wasn’t on the pill and asked him to pull out before he came. I was totally unprepared for what happened next!

He said, “OK, but can I cum in your ass instead?” I was shocked at what he said, not even sure if I had heard him correctly. Without thinking, and being totally “in the mood,” I think I just said, “OK.” I was super wet from having just cum. I was so wet I could feel the seat underneath me getting wet. Having never had “butt sex” before, or having never really thought about it, I was guessing I’d have to somehow roll over onto my stomach or get on my hands and knees in order for him to do it? As I was thinking about how this could be done in the backseat of a car, he pulled out, reached down to reposition himself, pushed my knees up toward my chest, and slowly entered my bottom! In my mind I was like, “Yikes!” It was pretty uncomfortable, but not as bad as I had supposed it would be. He slowly but surely pushed himself all the way into my bottom. I remember it hurting some and I remember feeling really full inside. He was gentle, which I was grateful for. He started working his way in and out of me for a few minutes then he “tensed up” and I could feel him cumming inside my bottom. A minute later, he pulled out, and I was grateful for the relief! We got dressed and returned to the reception. When we got back, I had to visit the ladies’ room to clean up. By that time, what he left in my bottom was coming back out into my panties! It was a bit of a mess. I was sore in “both places” the next day and a little “in shock.” Had I really let this guy put his penis into me everywhere? After my sister’s wedding, I’d see my brother-in-law’s brother occasionally at different family events. We never “did it” again and actually never even mentioned or talked about what we had done that day.

A month or so prior to my sister’s wedding I met the man who is now my husband. I had almost asked him to be my date to the wedding, but didn’t. A few months after my sister’s wedding I started dating the man that’s now my husband. Two and a half years later we got married. My sister was my Matron of Honor and her husband attended the wedding with her. I was pretty close to my brother-in-law’s family and several members of his family attended my wedding, including my brother-in-law’s brother. I felt a little “weird” about inviting him, but it would have been weirder not to. People would have wondered why. After our wedding, in the receiving line, when my brother-in-law’s brother came up to my husband and me, he shook my husband’s hand and said something like “I hope you enjoy your new bride!” – something like that. As he said that, he gave me a wink, which my husband couldn’t see. If felt really weird to be standing there in my white dress, with my new husband, and talking to the first guy to put a penis in my mouth and in my butt !!! I introduced him to my husband as “so and so’s brother.” What was I going to say, “Honey, this is the man that sodomized me in the back seat of a car several years ago. He’s also the last guy I had sex with prior to meeting you.” We see him from time to time at family gatherings. My husband has no idea. But, it’s still awkward for me.

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1 Comment

  • Reply Gonzo ID:7mkmumjj44

    Yeah I get that on occasion when I have met my daughter old friends that are married. Poor husband doesn’t have a clue I fucked the daylights out of his wife when she was younger for many years and some still to this day and their young daughter lol. Life can be amazing at times.
    Good story for sure.