NYCareacuckold Posted June 21, 2023 Report Share Posted June 21, 2023 My wife is a businesswoman who works in a suburban office building in the NY metro area. She works with a number of men at her office. I often fantasize about her having an affair with one of her male coworkers (maybe they would screw in her office or go to a hotel at lunchtime to have sex). Would anyone recommend a website on the subject of businesswoman/ladyboss cuckolding that they especially like? Thanks! Quote Link to comment Share on other sites More sharing options...
leone55 Posted June 21, 2023 Report Share Posted June 21, 2023 4 hours ago, NYCareacuckold said: My wife is a businesswoman who works in a suburban office building in the NY metro area. She works with a number of men at her office. I often fantasize about her having an affair with one of her male coworkers (maybe they would screw in her office or go to a hotel at lunchtime to have sex). Would anyone recommend a website on the subject of businesswoman/ladyboss cuckolding that they especially like? Thanks! Would your wife like to be screwed by a coworker, did you talk about? 2 Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted June 23, 2023 Author Report Share Posted June 23, 2023 No coworker specifically at the moment. But when we were newly married and in graduate school in our 20s, there was a 30-year-old guy who wrote an email (!) to my wife saying that he was very attracted to her, even though he knew she was married. 😳 She was also attracted to him. I should have let my wife have sex with him. It would have made her (and me) and her would-be lover happy. 2 Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted July 15, 2023 Author Report Share Posted July 15, 2023 With regard to businesswoman cuckold subject matter, it looks like the “business woman” category at maturetube.com looks promising. Shouldn’t there be an entire website just dedicated to such videos, such as ladybossporn.com, for example? Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted November 5, 2023 Author Report Share Posted November 5, 2023 On 6/21/2023 at 2:36 AM, leone55 said: Would your wife like to be screwed by a coworker, did you talk about? Yes, we talked about it a bit. Nothing came out of it, though. By the way, is that actually your cock in your profile pic? Quote Link to comment Share on other sites More sharing options...
Guest Posted November 5, 2023 Report Share Posted November 5, 2023 Honestly sounds hot Quote Link to comment Share on other sites More sharing options...
leone55 Posted November 5, 2023 Report Share Posted November 5, 2023 6 hours ago, NYCareacuckold said: Yes, we talked about it a bit. Nothing came out of it, though. By the way, is that actually your cock in your profile pic? Yes, it is. 1 Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted November 5, 2023 Author Report Share Posted November 5, 2023 Wow. 😳 Wives must like it. 🙂 Quote Link to comment Share on other sites More sharing options...
leone55 Posted November 26, 2023 Report Share Posted November 26, 2023 On 11/5/2023 at 4:18 PM, NYCareacuckold said: Wow. 😳 Wives must like it. 🙂 They do. 1 Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted December 10, 2023 Author Report Share Posted December 10, 2023 On 11/26/2023 at 2:47 AM, leone55 said: They do. I’d imagine so. 🙂 By the way, do you only have sex with Italian wives, or do you also screw wives from foreign countries? I wish that my wife would be interested in traveling to Italy with me so that we could have a hotwife / cuckold experience. I doubt she has seen a cock as large as yours, though. It might be intimidating. Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted December 10, 2023 Author Report Share Posted December 10, 2023 On 11/4/2023 at 11:02 PM, starkybull said: Honestly sounds hot Yes, sir. I like the idea a lot. I’d especially like to see the sexy mature businesswoman website contain plenty of images of bbw blonde businesswomen in their 50s who are cuckolding their husbands. Then again, I’m biased. 🙂 Actually, I’ll bet that a lot of younger guys who would like to have sex with a married woman would be more than willing (maybe eager) to give a good screwing to a mature, chubby, married businesswoman. They’d probably like to give her a load of spunk to take home to hubby. Quote Link to comment Share on other sites More sharing options...
leone55 Posted December 10, 2023 Report Share Posted December 10, 2023 6 hours ago, NYCareacuckold said: I’d imagine so. 🙂 By the way, do you only have sex with Italian wives, or do you also screw wives from foreign countries? I wish that my wife would be interested in traveling to Italy with me so that we could have a hotwife / cuckold experience. I doubt she has seen a cock as large as yours, though. It might be intimidating. No, of course I have sex mainly with italian wives as I live in Italy, but I also date foreign sluts that eagerly want to have sex with me. About your businesswoman check your p.m. 1 Quote Link to comment Share on other sites More sharing options...
Guest Posted February 12 Report Share Posted February 12 On 12/10/2023 at 11:32 AM, NYCareacuckold said: Yes, sir. I like the idea a lot. I’d especially like to see the sexy mature businesswoman website contain plenty of images of bbw blonde businesswomen in their 50s who are cuckolding their husbands. Then again, I’m biased. 🙂 Actually, I’ll bet that a lot of younger guys who would like to have sex with a married woman would be more than willing (maybe eager) to give a good screwing to a mature, chubby, married businesswoman. They’d probably like to give her a load of spunk to take home to hubby. I honestly am so hard at the thought of cucking another man and taking away his wife's panties right after I fill her up. I'd love to get texts from her man when she's dripping out and he's salivating so hard that he can't resist the thought of cleaning her up. Of course, subject to me permitting him :) Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted February 13 Author Report Share Posted February 13 As a bull, you seem to be in luck, because there appear to be more and more guys who would like their wives to cuckold them (and oftentimes the women seem happy to oblige). 🙂 Quote Link to comment Share on other sites More sharing options...
leone55 Posted February 13 Report Share Posted February 13 1 hour ago, NYCareacuckold said: As a bull, you seem to be in luck, because there appear to be more and more guys who would like their wives to cuckold them (and oftentimes the women seem happy to oblige). 🙂 Can we see something of your businesswoman wife? What's her actual age? Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted February 25 Author Report Share Posted February 25 She’s 58 years old. Quote Link to comment Share on other sites More sharing options...
Guest Posted February 29 Report Share Posted February 29 On 2/13/2024 at 11:55 AM, NYCareacuckold said: As a bull, you seem to be in luck, because there appear to be more and more guys who would like their wives to cuckold them (and oftentimes the women seem happy to oblige). 🙂 I'm sure you're going to be a good little boy and give us all a show and tell, to start things up. Quote Link to comment Share on other sites More sharing options...
geoffrey1963 Posted May 26 Report Share Posted May 26 My wife has had several "affairs" with men she has worked with. One was with the son of the company's owner. It began innocently enough, office flirtations, then lunches. The company sponsored a co-ed softball team, and he recruited my wife to play. As her spouse I was grudgingly invited to join the team also. After games we would all gather at local bars. We usually couldn't stay late, as we had a babysitter at home needing to get up for school the next day. One evening I offered to let her stay while I'd go home to allow the babysitter to get home. She eagerly accepted, telling me she'd get a ride home with someone from work. I finally heard her sneak in at...FOUR a.m! I pretended to be asleep as she slipped into bed, and yes, I could smell the sex on her. When we got up for work three hours later I said I'd gone to bed at 11 the evening before and asked what time she'd gotten home. She said "Ohh, around midnite I think." LIAR! I checked her panties in the laundry later and found the crotch stiff with dried sperm! Full disclosure...I jerked off with those panties before I left for work. After that her work schedule seemed to shift a bit. She'd go into the office earlier, or "need to stay later" more frequently. Our sex life became less frequent, though I did really get off when I could feel she was slightly gooey from his jizz. She'd pass it off as being extra excited, and that was fine with me. After a few months she announced she was pregnant with "our" third... 1 Quote Link to comment Share on other sites More sharing options...
leone55 Posted May 27 Report Share Posted May 27 On 5/26/2024 at 5:12 PM, geoffrey1963 said: My wife has had several "affairs" with men she has worked with. One was with the son of the company's owner. It began innocently enough, office flirtations, then lunches. The company sponsored a co-ed softball team, and he recruited my wife to play. As her spouse I was grudgingly invited to join the team also. After games we would all gather at local bars. We usually couldn't stay late, as we had a babysitter at home needing to get up for school the next day. One evening I offered to let her stay while I'd go home to allow the babysitter to get home. She eagerly accepted, telling me she'd get a ride home with someone from work. I finally heard her sneak in at...FOUR a.m! I pretended to be asleep as she slipped into bed, and yes, I could smell the sex on her. When we got up for work three hours later I said I'd gone to bed at 11 the evening before and asked what time she'd gotten home. She said "Ohh, around midnite I think." LIAR! I checked her panties in the laundry later and found the crotch stiff with dried sperm! Full disclosure...I jerked off with those panties before I left for work. After that her work schedule seemed to shift a bit. She'd go into the office earlier, or "need to stay later" more frequently. Our sex life became less frequent, though I did really get off when I could feel she was slightly gooey from his jizz. She'd pass it off as being extra excited, and that was fine with me. After a few months she announced she was pregnant with "our" third... Are you sure your third is not yours? And the other two? Quote Link to comment Share on other sites More sharing options...
NYCareacuckold Posted July 19 Author Report Share Posted July 19 On 5/26/2024 at 11:12 AM, geoffrey1963 said: My wife has had several "affairs" with men she has worked with. One was with the son of the company's owner. It began innocently enough, office flirtations, then lunches. The company sponsored a co-ed softball team, and he recruited my wife to play. As her spouse I was grudgingly invited to join the team also. After games we would all gather at local bars. We usually couldn't stay late, as we had a babysitter at home needing to get up for school the next day. One evening I offered to let her stay while I'd go home to allow the babysitter to get home. She eagerly accepted, telling me she'd get a ride home with someone from work. I finally heard her sneak in at...FOUR a.m! I pretended to be asleep as she slipped into bed, and yes, I could smell the sex on her. When we got up for work three hours later I said I'd gone to bed at 11 the evening before and asked what time she'd gotten home. She said "Ohh, around midnite I think." LIAR! I checked her panties in the laundry later and found the crotch stiff with dried sperm! Full disclosure...I jerked off with those panties before I left for work. After that her work schedule seemed to shift a bit. She'd go into the office earlier, or "need to stay later" more frequently. Our sex life became less frequent, though I did really get off when I could feel she was slightly gooey from his jizz. She'd pass it off as being extra excited, and that was fine with me. After a few months she announced she was pregnant with "our" third... That’s a sexy experience. It sounds like your wife’s coworker had a big load for her. You’re a lucky guy. 😊 I’ll bet that he is also big-cocked. When my wife told me about how a much younger male coworker had winked at her in a business meeting, I was left wondering how much he lusted for her and if he has a lot of spunk. 😯 Quote Link to comment Share on other sites More sharing options...
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