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My best friends dad

1364 words | 5 |4.46
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Everyone in town knew that I was very feminine and dressed only as a girl. My best friend was a girl. We use to talk about boys and compare them.
Well one day I was over her house we were sitting outside when her dad came home and said that we look very cute and adorable dressed like same. He sat down we were talking about stuff he mentioned about how we were both 16. Then he said had a question for us. She said what an he asked us if we were having sex with each other. She said no that we both like guys. He asked me if that was true. I said yes it was . He rubbed my smooth stocking covered leg and said ok.
I didn’t know what that was about an asked her after he left. She said that she didn’t know. So we just went about our business. Over the next few days he was being extra fun and nice to me. We hung out for the next few days because she was going to spend couple of weeks with her grandparents. She asked me to stop by and check on him.
She had been gone a couple of days that morning I had put on a purple corset and tan seamed thigh high stockings after I took a bath and did feminine stuff. I did my hair and makeup and lipstick. Since my mom and I just got our nails filled done and painted. I decided to wear my dark purple zip up body con mini dress and 5″ open toe stilettos. After I put my earrings in and jewelry on and stuff. I decided to go by there to see if he needed anything. So I walked to there and knocked on the door. He invited me in .
We talked for a while when he asked me if I really liked guys and I said yes. He said that was nice and my mom knows that I do. I said yes she does. Then I asked him if he needed anything. He said maybe he shouldn’t ask me this but would I sit across his lap and let him hold me. I said yes I would. So I got up and sat across his lap he put his hands and arms around my waist tight and I just put my arms around his neck. He held me for a while then he asked me if he could give me a kiss. I said yes he could. He kissed me on my sparkling red lipstick lips for a few seconds and then he kissed me again but this time we ended up kissing long and passionate. I was a bit surprised by it. When he said that he should be honest with me that he was attracted to me. I said but you were married before your divorce. He said that only reason he was married to Tina’s mom was because he got her knocked up. But he could never fight the feelings he had for girly boys like me. I said that I had no ideal he was.
Well he kissed me passionately after he told me that . I put my head on his shoulder he had moved his hand was stroking my stocking covered thighs commenting on how smooth my legs are and sexy they look. He said that he liked that my stockings were thigh high stockings. I softly moaned as he did. With my head on his shoulders still I asked him if there was anything else he needs or wants. He said yes but he shouldn’t ask me. I said whatever you want ask me. He whispered in my ear and said you and I in bed together. I kissed him and said yes and stood up and kissed him and told him to give me a minute and come in his bedroom. I went in his room and took my dress off so I was just in my corset and stockings g-string and high heels. I laid down on the bed. He came in and stripped all of his clothes off. He got over me and started to kiss me we kissed passionately rolling on to our sides. As we kissed I was playing with his cock and balls. He said that I didn’t have to do this I said that I promised Tina that I would take care of you but I want to. I pushed him on his back and kissed his lips and worked my way down his chest and stomach. I kissed and licked his cock and balls. He was hard so I licked my way up his hard 7.5″ taking it in my mouth and going completely down on it to his balls. I slowly keep sucking him this way and and once an while running my tongue around the head of it. He told me how great it was. Then he kept calling me baby and how sexy I was. I had been sucking him for about 20 minutes when he started to tense up and he said that he was going cum. I went completely down on him and he shot his hot load in my throat and mouth. He couldn’t believe that I swallowed every single drop of it. After I made sure I got all it he pulled me up. He started kissing me passionately and telling me how wonderful it was and how much he loved seeing my lipstick lips around his cock. I told him that I loved doing it and how much I love sucking him.
We laid there for a good while kissing and cuddling with him. When he asked me what time I had to be home. I told him that we had all day . He said you mean that I can make love to you also. I said yes you can as well. He started to kiss me our tongues intertwined in each other’s mouths. He was over top of me my arms tightly around his neck. I was so relaxed and couldn’t believe it that I was with my best friends dad. He started to kiss and suck my neck. He kept doing this for a while I wrapped my legs around him and he lubed his cock and I felt the tip of it against my sissy boy pussy and then he slowly slipped in me. I moaned as he slid in me balls deep. He slowly fucked me I was moaning loudly he seemed to slowly fucked me for a hour his cock felt so amazing slowly pumping in out of me. After a good while he got faster and then shot his hot load deep inside of me making me moan very loudly. During the rest of the day I sucked him and he fucked me in different positions giving me his load every single time.
I got dressed to go home full of his seed I was feeling amazing but a bit guilty about having sex with my bff dad but I wanted to again. Well I went home thinking about it. Later on that evening Tina called me we talked about stuff and she asked me if I had seen her dad and I said yes. She asked if he was doing ok. I said that he was doing great and that I helped him with something today. She said that she was going to call me back in a few minutes and then hung up. She called back a few minutes later. We were talking about stuff and she said that she was talking with her dad and he told her what happened between us. I figured that she was going to be pissed off. Then she said that she wanted to know everything so I told her. She said that was great. She asked me what I was doing now. I told her just sitting at home watching TV. When she said that I should go stay with him for a few days and I said you don’t mind me having sex with him. She said that she didn’t mind at all.

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5 Comments

  • Reply DancesNaked ID:1daoi3jd28pj

    I would love to read how he took his young sissy on a date or two. Please write more to this story!

  • Reply Joe ID:7481adjbm1

    I wish I could have a young sissyboy to look after my needs in the bedroom

  • Reply Blackbear7 ID:7zv3ebba43

    Hmm, love the story. PappaBear needs a neighbor boy like that next door. I will be a real good daddy to her.

  • Reply [email protected] ID:1dc16zbamh9o

    He sounds wonderful. Be good to daddy

    • daddy1980 ID:sfrud5jlbj4

      daddy love a good sissyboy