Me and my wife were dating at the time. After a good night, both of us spent, I asked a question that would change our relationship until this very day. I was 23, she was 18. She was slim, 5'3", maybe 100 pounds, 34b breasts, with a teardrop ass that was amazing. Long dirty blonde hair that reached her lower back. Snuggling with her, I asked her what was her most secret fantasy. I had to ask a few times, I think because she feared my reaction. Assuring her, no matter what it was, it was only a fantasy. She finally admitted, she wanted a MFM threesome. Then she asked mine. Almost instantly, I answered, FMF threesome. She related, she would not want me to have such a fantasy come true. She couldn't handle herself seeing me with another girl. When I told her, the love I had for her, me being a lil older, not wanting to rob her of her youth, and if we were to be together, I didn't want her to have any regrets. I didn't want her, later down the road, to blame me for anything she would have missed out on. I would help to make any and all of her fantasies come true.
The conversation dwindled down, but stayed in my head. Over the next couple of months, I would bring the subject up while having sex with her. It was to the point where she was avoiding any answers to my questions, and I would tease her by stopping or slowly pumping her, going deep, waiting a few seconds, before doing it over and over, driving her crazy, waiting for an answer. It was great sex, but I could only imagine how much she would be into having to take care of 2 guys at one time. Asking her if she really wanted to try it, her, delaying an answer, then finally the words passing her lips that she really wanted to. Only then, I would pump as hard, deep, and fast as I could and blow my load. Every session, more details would emerge of what she really wanted. It was a part of our love making. More pillow talk, was all the things I had asked, the answers she had given, she finally asked if I was serious about the scenario. Of course I was, I had no idea how to make it happen, but I would be ok if it did.
Asking her, who she had imagined doing this with, she said she didn't want to choose a guy, that I may read more into that than there actually was. She said she wanted me to find a guy for her. To let her know who, and she would let me know if she would be ok with him. So, the wheels were turning. Who can the guy be? A friend? A stranger? The thought of a stranger didn't strike me as a good choice. The thought of a friend, it was the same thoughts. How do I ask a guy that I want him to join me doing my girlfriend? I decided a not so close friend. Someone I knew, almost a friend, but not. Asking a real friend, could ruin a friendship if he wasn't into that. Asking a stranger felt it would just be creepy. Someone I knew, but not close, his reaction wouldn't have been a big deal if he refused. And I could have played it off like I was joking with him.
In the following couple of weeks, she would ask if I found someone yet. The pressure was on. I finally confided with my boss. He wasn't a real friend. He knew something was up with me. Lack of concentration on my work. I told him what was going on with me and my girl. Telling him, asking him not to judge, I thought me confiding would make our friendship better. Expecting advice, even consultation went right out the window when he said he would fuck her, and I wasn't expecting that answer. He was 39yrs old, married. I didn't consider asking him to do anything before. Since he offered, I saw him in a different light. I wasn't sure if my girl would allow a guy more than twice her age fuck her. She had met him a few times. So she knew who he was, what he looked like. He was always polite to her. My boss told me to tell her he would love to fuck her.
That night, I brought the subject up and hinted I had a prospect, she asked if I found someone. I asked her what she thought of my boss. She was shocked, not thinking I was serious. She did say she thought he was handsome, but married. That he wouldn't want to do such a thing. I said nothing. Thinking it would have to be a surprise for her. The next day, she was staying at my apartment when I went to work. I would be at work for the lunch shift. I would be back in a few hours. At work, my boss pulled me in his office, and asked if I told her. I told him what she said. I told him, too bad he would be at work all day, cuz we could go surprise her when I got off work. He reminded me, he was the boss, and that day was the day. He was gonna visit, try his luck, and if it didn't work out, it was all good either way.
