(Likely not in the correct order)
1. Dated a girl, she broke it off with me. She set me up with her friend. I went to a house where her friend was housesitting and we all ended up in bed together to sleep. This girl (not the friend) and I start messing around, then I end up entering her...trying to keep the bed still. We both came, then the girl whispers to me, "I can't believe I just fucked the guy my best friend wants" .
2. My first true experience with a woman. Sure, I'd fooled around with some girls in Jr and high school up to that point, but this was a teaching moment! We met at a charity event, she was 36, I was 16. We chatted, danced and I walked her back to her accommodations. We started making out on her doorstep and I (naively) started pawing at her breasts. She slowed me down, teaching me to listen and feel a woman's body. I'm sure many woman have been the grateful recipients of the lessons learned that day! We never had sex, but such an awesome experience!
3. First online meeting - just a simple chat room, only to discover a woman lived near me. We created a meeting game where we would meet at a pub and the only thing I knew about her was that she was blonde. So I was to go to every blonde in the place and say something dirty to them until I found her. Turns out we couldn't meet the first time. So I asked about the following wednesday, to which she said she couldn't because she was taking lessons at a local billiards club, but that Friday would work. So what do I do? Go to the billiards club on Wednesday of course and "pre-scout" ! Friday comes along, I see her walk into the club and go straight to her and whisper "gawd you look sexy tonight". The look she gave when a) I found her so quick, and b) that she found me attractive! She was a great lover, but was in a long distance relationship she didn't want to end.
4. This could count as two, but the individual experiences with two married women. Different circumstances and times in my life, but to have so much meaning to someone's life and the secrecy of it all are things I'll never forget or regret.
5. (and why I'm on this site). The first time I discovered I wanted to watch my wife with another man. The anguish of the evening, but the voyeuristic approach I was taking! We were out of town and at a massive social gathering. I was tired and tired of drinking so started off to bed early (well....1230am if that's early), expecting the wife to be there shortly after (as her and I were both horny after a day of flirting, drinking, having fun). I woke up at 230am and she wasn't there. Fueled with some anger and fear of her safety, I set off to find her. I remembered the group she ended up with and one guy stood out in particular.... Then I thought what will I say when I find her? What will I do? And what if she's in the throws of passion (or likely just getting fucked....let's be honest here....lol)? I came to the decision that if I found her in a sexual activity, that I would just watch from a distance and let her finish....there's a few previous instances from our past that fuelled that thought....ones which one day I am sure I will elaborate on....much also to what I thought I discovered later about this event..... But what stands out the most is just that feeling in my gut, but the pure voyeur and fan (of my wife) shining through the feelings of angst!
