Straight Male / 27
So I've been at the same job for ten years now (first job since leaving school) working as an assistant for an older (in her 40's), attractive woman. Let's call her Jen so it stays anonymous. We've always had a very good working relationship and clicked from day one having playful banter and harmless flirting.
About a year ago she separated from her husband (they're still married, just having some time apart) and the flirting and the jokes between us got a little heavier and slightly dirtier but nothing too over the top. She was much happier after separating from her husband and went out on the town a lot more and one night I bumped into her at a local bar. Both of us were pretty hammered and our harmless flirting turned into us grinding against each other on the dance floor which eventually led to us kissing. At one point she whispered into my ear 'I've wanted you for years. I need you' but sadly before anything could go any further her friend told her they had to leave.
The following weeks at work was like nothing had happened and neither of us spoke about it until one day she called a meeting with myself and two other colleagues to say all of us were going on a business trip to Dublin for 3 days (2nights). I was buzzing as I'd never been on a business trip before. Then after the meeting she asked for me, just me, to stay behind. She told me that she wasn't going to be suitable during this business trip and she was tried of waiting for me to make the first move. I couldn't believe what I was hearing. My heart was pounding with adrenaline and my cock was throbbing in my trousers. I was speechless. Then she stood up, staring into my eyes and said 'you want this just as much as I do, so give in to temptation, stop fighting your urges and let me show you how a real woman fucks'. I now had a raging hard on and stood up and simply said 'yes ma'am. I can't wait' and walked out.
The following week we arrived at the hotel and as I was settling in I heard a knock at my door. Just as I went to open the door Jen burst through, slammed the door behind her, threw me against the wall and started roughly and passionately kissing me while pulling her clothes off. We were both naked, literally, within seconds except for her underwear and tights. She was stroking my cock with both hands while passionately kissing me and before I knew it she was on her knees sucking my rock solid cock. I was preparing for something to happen but nothing like this. She really wasn't kidding when she said she was coming for me. I couldn't hold on for long and within in seconds I blew a massive load in her mouth and she took every. Single. Drop. And swallowed it while staring into my eyes. She was incredible. But before I could say anything she simply stood up and said 'my turn!', then threw herself onto her back onto the bed, spread her legs, ripped a hole in the crotch of her tights and signaled me to come to her. I practically ran over to her and pulled her underwear to one side and began to tongue and finger fuck her soaking wet, completely shaved pussy. I wasn't even paying attention to what I was doing, just listening to her moans and crys for more when I suddenly realised I was no longer tongue fucking her pussy but had moved down to tight, pink ass hole. I shocked myself as I'd never even thought of eating someone's ass but I, like her, was loving every second of it to the point I was rock hard again. The moment she said she needed me to fuck her I leaped to my feet and slid my cock deep and hard inside her without any hestitation or teasing. I needed her. I needed to be inside her. Standing at the end of the bed with her legs over my shoulders I fucked her fast, hard and deep for only a few minutes before blowing my load deep inside her dripping wet pussy while she was locking eyes with me moaning 'yes that's it, cum inside me, that's it, give me that young hot cum'. She was truely, the best fuck I've ever had.
We lay there for a couple of minutes saying how great that was and that it needs to happen again when she got up and got dressed and left a copy of her key on my drawers after kissing me passionately once more.
We fucked a total of 6 times during that business trip two weeks ago have met up once more since getting back and have plans for a weekend of naked fun this weekend. She's the most incredible woman I've ever been and I can't recommend older women enough. She know how to work a cock.
My real confession here is that I think I'm getting feelings for her but I don't know how she feels. I don't want any other women. I don't need anyone else. But I also don't know how my parents will feel if I tell them I'm fucking my boss who's nearly 20 years older than me... either way, I will not stop fucking Jen for anyone.
About a year ago she separated from her husband (they're still married, just having some time apart) and the flirting and the jokes between us got a little heavier and slightly dirtier but nothing too over the top. She was much happier after separating from her husband and went out on the town a lot more and one night I bumped into her at a local bar. Both of us were pretty hammered and our harmless flirting turned into us grinding against each other on the dance floor which eventually led to us kissing. At one point she whispered into my ear 'I've wanted you for years. I need you' but sadly before anything could go any further her friend told her they had to leave.
The following weeks at work was like nothing had happened and neither of us spoke about it until one day she called a meeting with myself and two other colleagues to say all of us were going on a business trip to Dublin for 3 days (2nights). I was buzzing as I'd never been on a business trip before. Then after the meeting she asked for me, just me, to stay behind. She told me that she wasn't going to be suitable during this business trip and she was tried of waiting for me to make the first move. I couldn't believe what I was hearing. My heart was pounding with adrenaline and my cock was throbbing in my trousers. I was speechless. Then she stood up, staring into my eyes and said 'you want this just as much as I do, so give in to temptation, stop fighting your urges and let me show you how a real woman fucks'. I now had a raging hard on and stood up and simply said 'yes ma'am. I can't wait' and walked out.
The following week we arrived at the hotel and as I was settling in I heard a knock at my door. Just as I went to open the door Jen burst through, slammed the door behind her, threw me against the wall and started roughly and passionately kissing me while pulling her clothes off. We were both naked, literally, within seconds except for her underwear and tights. She was stroking my cock with both hands while passionately kissing me and before I knew it she was on her knees sucking my rock solid cock. I was preparing for something to happen but nothing like this. She really wasn't kidding when she said she was coming for me. I couldn't hold on for long and within in seconds I blew a massive load in her mouth and she took every. Single. Drop. And swallowed it while staring into my eyes. She was incredible. But before I could say anything she simply stood up and said 'my turn!', then threw herself onto her back onto the bed, spread her legs, ripped a hole in the crotch of her tights and signaled me to come to her. I practically ran over to her and pulled her underwear to one side and began to tongue and finger fuck her soaking wet, completely shaved pussy. I wasn't even paying attention to what I was doing, just listening to her moans and crys for more when I suddenly realised I was no longer tongue fucking her pussy but had moved down to tight, pink ass hole. I shocked myself as I'd never even thought of eating someone's ass but I, like her, was loving every second of it to the point I was rock hard again. The moment she said she needed me to fuck her I leaped to my feet and slid my cock deep and hard inside her without any hestitation or teasing. I needed her. I needed to be inside her. Standing at the end of the bed with her legs over my shoulders I fucked her fast, hard and deep for only a few minutes before blowing my load deep inside her dripping wet pussy while she was locking eyes with me moaning 'yes that's it, cum inside me, that's it, give me that young hot cum'. She was truely, the best fuck I've ever had.
We lay there for a couple of minutes saying how great that was and that it needs to happen again when she got up and got dressed and left a copy of her key on my drawers after kissing me passionately once more.
We fucked a total of 6 times during that business trip two weeks ago have met up once more since getting back and have plans for a weekend of naked fun this weekend. She's the most incredible woman I've ever been and I can't recommend older women enough. She know how to work a cock.
My real confession here is that I think I'm getting feelings for her but I don't know how she feels. I don't want any other women. I don't need anyone else. But I also don't know how my parents will feel if I tell them I'm fucking my boss who's nearly 20 years older than me... either way, I will not stop fucking Jen for anyone.
- That's Juicy! 33
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