Straight Female / 28
My First Anal
I work for this man, we are close. When I was new to the company, I was 22 and it was my first office job out of college, I signed up for the charity bike ride. He saw my name on the list and told me he didn't want me to ride. He whispered that the nerves to my vagina could be damaged. To read up on it, and stay off a bike for such a long ride.
I opted out because I didn't want to offend him. While half the office was either on bikes or working support he took me to lunch. He repeated his claim that the nerves in my vagina could be damaged, and a young woman should want her vagina to be as sensitive as nature meant for it to be. He also claimed that riding bikes long distance could also ruin the nerves in my anus. A lunch talking with this man about my vagina and my anus, and how he wanted me to remain intact, very sensitive.
Several months later he and I were at Macy's and he told me that thongs were bad for me. He showed me some panties he liked and bought them for me. I went back to the office with panties my boss had bought me.
When the conversation came up about anal massage it was a full blown discussion, telling me how he would massage my anus. He told me he would lay me naked on his bed, lube his fingers and gently but firmly massage my anus. And he would draw an orgasm out of me, guaranteed. I should take him up on it.
I laid on my bed, totally naked, he kissed the back of my neck, he pressed his index finger in my crack. My legs slowly opened, he stuck his finger in my vagina, he then rubbed my anus. Gently, firmly, pressing, not penetrating, kissing my neck, telling me he wanted me to dream about his penis penetrating me. When he got on my back, when his penis started rubbing against my anus I closed my eyes as tight as I could, holding my breath.
Penetration was slow, intense, on purpose, his hot penis tearing me a new asshole, his hot breath on my neck, I envisioned the big bad wolf fucking Red Riding Hood. Until it was over, no longer just my boss now he owned me.
I opted out because I didn't want to offend him. While half the office was either on bikes or working support he took me to lunch. He repeated his claim that the nerves in my vagina could be damaged, and a young woman should want her vagina to be as sensitive as nature meant for it to be. He also claimed that riding bikes long distance could also ruin the nerves in my anus. A lunch talking with this man about my vagina and my anus, and how he wanted me to remain intact, very sensitive.
Several months later he and I were at Macy's and he told me that thongs were bad for me. He showed me some panties he liked and bought them for me. I went back to the office with panties my boss had bought me.
When the conversation came up about anal massage it was a full blown discussion, telling me how he would massage my anus. He told me he would lay me naked on his bed, lube his fingers and gently but firmly massage my anus. And he would draw an orgasm out of me, guaranteed. I should take him up on it.
I laid on my bed, totally naked, he kissed the back of my neck, he pressed his index finger in my crack. My legs slowly opened, he stuck his finger in my vagina, he then rubbed my anus. Gently, firmly, pressing, not penetrating, kissing my neck, telling me he wanted me to dream about his penis penetrating me. When he got on my back, when his penis started rubbing against my anus I closed my eyes as tight as I could, holding my breath.
Penetration was slow, intense, on purpose, his hot penis tearing me a new asshole, his hot breath on my neck, I envisioned the big bad wolf fucking Red Riding Hood. Until it was over, no longer just my boss now he owned me.
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