Straight Male / 28
Assistants Friend
My assistant at work is 34 years old, I'm 28. She and I have danced around sexy innuendo for some time and finally we fucked. No dating just fucking. That is her way of handling things, no dates, she dates others but doesn't fuck them, and I believe her. I mostly fuck her and only go out on dates very occasionally. we fuck almost every weekend from Friday through Monday, and at least twice sometimes three times a week. Whenever she wants it, and she wants it often. We're not comfortable enough to fuck during her periods, before she wouldn't have me over during that time but now we do. She is quite sexy, though a bit thick. So in that respect I'm glad it will not progess to marriage, but she's still sexy as hell, nice plump, soft tits that are very sensitive at her quarter sized, dark aureolae and nipples that get as firm as pencil erasers when she cums. She wasn't much into anal, but she did it for me and now actually enjoys it and sometimes asks for it. She swallows my cum, takes it on her face or her tits, and I can cum bareback inside her ass or pussy.
She got really serious on me about two months ago, my cum deep in her pussy and another load down in her belly from her swallowing, and asked me if I'd agree to fuck her friend. I wasn't sure why, or who but asked. It was Joli her friend who is 34 years old, thin, I'd say a size 4 dress, Acup titties I'm guessing, and as I was to find out a natural blonde. Joli is very pretty and shouldn't have trouble getting any guy, so I asked why. My asst. told me that Joli was a virgin and at 34 wanted to have sex and couldn't bring herself to ask anyone to do it and admit that after all this time she was still "intact". I asked my asst. just want it was like her first time, and she said it was less than stellar, and very uncomfortable to painful. I told her that it only got better with doing it more. So I didn't want to be remembered as the painful, uncomfortable one and have Joli think that sex was like that.
It was agreed that I'd take some of my time from my asst. and fuck Joli over a couple of months ending when she wanted to find someone else. I also added that she'd have to suck me to cumming and swallow, evidently Joli did that already, so that was agreed, but she'd not had anal and I had to have her all three ways I said. It was agreed, and my date with Joli was arranged. Prior to that she sucked me off at my place with my asst watching. She swallowed while I was kissing her and reaching under her tee shirt to her braless little titties. I took Joli out to dinner, theater and we went to an expensive hotel suite. I seduced her in all the right ways, we both know it wasn't seduction, I was going to fuck her but I played the game and she loved it. I ate her blonde haired pussy till she came twice and almost on the third time cumming I plunged into her pussy, a gasp and couple of strokes and she was cumming for her third time. You could tell after there was some discomfort, and I came inside her looking into her eyes and telling her she was beautiful and sexy, then kissing her deeply.
I fucked her three times that night, ate her every time, and she was very willing to continue. After a month I'd fucked her asshole a few times and she got used to that, got used to sucking and swallowing, and getting fucked and cumming. My assistant was asking for all the details and in giving them I got even better fucks from her than I'd had for a while. I did the deed, Joli has had sex with two other guys, and sometimes comes over for me to fuck her in front of my assistant, who loves to watch.
I was hesitant but now am glad I helped her out. She's turned into a very beautiful woman now, she takes care of her appearance and her style, her dress everything. She's turned very sex.
She got really serious on me about two months ago, my cum deep in her pussy and another load down in her belly from her swallowing, and asked me if I'd agree to fuck her friend. I wasn't sure why, or who but asked. It was Joli her friend who is 34 years old, thin, I'd say a size 4 dress, Acup titties I'm guessing, and as I was to find out a natural blonde. Joli is very pretty and shouldn't have trouble getting any guy, so I asked why. My asst. told me that Joli was a virgin and at 34 wanted to have sex and couldn't bring herself to ask anyone to do it and admit that after all this time she was still "intact". I asked my asst. just want it was like her first time, and she said it was less than stellar, and very uncomfortable to painful. I told her that it only got better with doing it more. So I didn't want to be remembered as the painful, uncomfortable one and have Joli think that sex was like that.
It was agreed that I'd take some of my time from my asst. and fuck Joli over a couple of months ending when she wanted to find someone else. I also added that she'd have to suck me to cumming and swallow, evidently Joli did that already, so that was agreed, but she'd not had anal and I had to have her all three ways I said. It was agreed, and my date with Joli was arranged. Prior to that she sucked me off at my place with my asst watching. She swallowed while I was kissing her and reaching under her tee shirt to her braless little titties. I took Joli out to dinner, theater and we went to an expensive hotel suite. I seduced her in all the right ways, we both know it wasn't seduction, I was going to fuck her but I played the game and she loved it. I ate her blonde haired pussy till she came twice and almost on the third time cumming I plunged into her pussy, a gasp and couple of strokes and she was cumming for her third time. You could tell after there was some discomfort, and I came inside her looking into her eyes and telling her she was beautiful and sexy, then kissing her deeply.
I fucked her three times that night, ate her every time, and she was very willing to continue. After a month I'd fucked her asshole a few times and she got used to that, got used to sucking and swallowing, and getting fucked and cumming. My assistant was asking for all the details and in giving them I got even better fucks from her than I'd had for a while. I did the deed, Joli has had sex with two other guys, and sometimes comes over for me to fuck her in front of my assistant, who loves to watch.
I was hesitant but now am glad I helped her out. She's turned into a very beautiful woman now, she takes care of her appearance and her style, her dress everything. She's turned very sex.
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