As for my first time with a man, it was with a girl I was having an affair with, she worked for me at the company where I worked at the time, and her father. At the time this all took place, she was 32, I was 44 and her father was 48. He had fathered her with a woman 10 years older than him when he was 16.
Yvonne and I had talked about having a 3 some and we had both indicated an interest in bi sex. She especially was turned on by the thought of seeing me loose my oral and anal cherry. She had fucked me several times with a dildo and I loved it and she really wanted to see me get fucked by a man.
We had arranged a weekend getaway to the Dells in Wisconsin and were to meet for breakfast on Sat. morning early. She had told me she had a surprise for me but little did I know. When I arrived at the restaurant, she was already seated and was with a man.
I walked over to them and he stood as I approached the table and she introduced us and told me he was her father. I was a little shocked she had brought him along and was not sure how he would react since she and I were both married but not to each other. Frankly, I was nervous as hell. We chatted a bit and finally she looked at me and said she had something very private and personal to tell me. I glanced at her father and he just sort of smiled at me. She cleared her throat and started telling me that her first sexual encounter had been with her father. I was stunned and had no idea what to say.
She went on to relate that he had taken her cherry on her 13th birthday - in fact, throughout that weekend he took all 3 of her cherries. She then told me that they had been lovers ever since. He asked me if I was alright with that and I sort of stammered that I didn't mind at all if that is what they both wanted. She told me he had also taken his son's cherries a little over a year later when he turned 18. That really blew me away. I just sort of sat there not quite knowing what to say or do.
Finally, Yvonne turned to me and told me that in truth she wanted her father to join us for the weekend and for us all to have sex together. I just sat there and her dad lay a hand on my shoulder and told me that if I was not comfortable with this that he would leave us and go back home. Well, the more I thought about it, the more turned on I began to get thinking of having the chance to see a father fuck his daughter so I finally told them I was OK with the deal.
We finished breakfast and drove up to The Dellsa and checked into the hotel where I had already reserved a room. I had to admit I was still nervous but also very excited as well. When we got to the room we sat around a bit just chatting and finally Yvonne got up and told us that she didn't know what we were there for but she was there to get fucked and started undressing. Her dad looked at me and smiled and said we might as well join her and stood up and started taking off his clothes. I did the same finally but with a lot of nervousness I have to admit.
Finally we were all three naked and I just gawked like a fool. Her dad was a nice looking man about the same height as me (6'2") and had a pleasant body. He was already hard and looked to be just a little longer and thicker than me. He turned to me and before I knew what was happening he pulled me to him and wrapped his arms around me and kissed me. I was so stunned that when his tongue hit my lips I automatically opened them and felt his tongue slip into my mouth.
God, could he kiss. It all of sudden hit me that I was kissing a man but he was so good all I could do by then was kiss him back. It also felt good to feel our cocks rubbing against each other. I don't really know how long we stood there kissing but I was aware Yvonne was moaning in my ear and I then realized she was pressed against my back and I could feel her tits rubbing all over my back and her hands caressing my ass.
I felt Yvonne slid down my back and she sort of Pushed us apart and turned us a little and then took her dad's cock in her mouth. She sucked him just a bit and then turned and took me in her mouth. She then started going back and forth between us sucking and licking both of our cocks. At one point, she was sucking me and her father reached down and took my hand and placed in on his cock. My fingers immediately closed around it lightly and I began to gently stroke him. It felt so natural and so wonderful as well. I love stroking my own cock and loved doing his even more.
Yvonne moved back over and took her father's cock in her mouth and took my hand and pulled me down to kneel beside her. She then took his cock out of her mouth and held it in her hand and directed it at me. He put his hand behind my head gently pulled me forward as she guided his cock toward my lips. He was leaking lots of pre-cum and when the head touched my lips it felt so right and natural and I just opened my mouth and took him in. As I did, Yvonne gasped out loud and said how beautiful that looked to see me with her father's cock in my mouth. He tasted wonderful I have to admit and I loved the taste and feel of his pre-cum coating the inside of my mouth.
.... There is more of this story ...