Sleeping with my boss

Dear Guys,

I’m 28 and I’ve been sleeping my boss who’s 54. We are hook up buddies. We both made it clear we didn’t want a relationship. We have been hooking up for six months. We have stuck to the rules until the last month or so. He’s been asking me to stay all night wanting to hang out at his house, and he’s been saying things like (This is the PG rated version. You can imagine what he’s really saying as he points to a certain part of my body.) “Who’s this belong too?” “You gonna share this with anyone else?” “I love this.” “I love sleeping with you.”

I’m not sure how to take any of these questions/comments. We went out to the bar together for the first time and he got there before me. When I arrived he informed me that the lady next to him asked him if he was there with anyone. I just looked at him and smiled and didn’t say anything. He then says “I told her my girl was on her way.” Again I just smiled and didn’t say anything. Once again I dont know how to take it. I’m confused about what should I do. Should I just let it go and see where it goes? Do I ask him where we stand? He wants to know who’s texting or calling me. He asks about my life. Does he want more than a hook up buddy relationship in your opinion?


Dear Allie,

The real question is, what do you want? You say you both made it clear you didn’t want a relationship but it sounds to us that you actually do in fact want a relationship with this man, otherwise you wouldn’t be wondering, or you wouldn’t care, what he’s thinking. Is that a fair statement?

You might want to read our e-report on Friends with Benefits/Hook Ups to see where we stand on these types of arrangements. But to sum it up. What we’ve learned over the years is that men enter into a hook-up arrangement because that’s exactly what they want. Women, on the other hand, enter a hook-up arrangement because that’s exactly what the man wants. Sure, some women feel as men do and are able to compartmentalize sex and love, but most women aren’t wired that way.

Okay, seminar over. You really want to know what he’s thinking? We’ll break it down for you.

First off, he’s sleeping with his employee, which is a huge no, no. We don’t know what business you’re in, but boss/employee relationships usually end at some point, and usually, not well. That’s definitely in the back of his mind, or at least, should be.  Secondly, the two of you are in very different places in life. Does he have an ex-wife? Kids? Is he divorced? It’s very unlikely he sees you as something more than a beautiful trophy he can brag about to his friends, and to strangers in a bar. How do you see him? That doesn’t mean he doesn’t care about you, it just means he isn’t thinking long-term. Third, he loves having sex with you. He’s thinking he’s hit the proverbial lottery getting to sleep with a woman almost 30 years younger than him. He says all those provocative statements  to you to keep you in the fold, a way to protect his “territory” so you won’t stray. Understand that he’s fully aware that he’s much older than you, and that you probably have other men interested in you. Even if he isn’t saying it, he feels insecure about the age difference.

Questions for you: What is your main motivation for being with him? Why a guy much older than you? What about a guy closer to your age? Someone you can build a life with? We’d love to know what you’re thinking.

If you’d like to continue this discussion, or you have follow-up questions/comments, leave them in the comments’ section below. (You must be Logged In to do so, due to all the SPAM we get.)

Take care,


ps. We hope you’ll let your friends know about us. Thanks! @TGPBuzz






47 Comments on Sleeping with my boss

  1. Fuckbuddy87 // January 27, 2016 at 10:23 am //

    Im in the middle of a separation. i was with my husband for 10year married 8. which is why i am ok with being FWB.i hit on him. I asked him if he wanted to be FWB not the other way around. Since writing this i have quit my job due to childcare issues. He still wants to see me ive tried walking away but he pulls me back in. He is single. He has four kids three of them are grown. He has not been married since he was in his 20’s the marrage only lasted 2years. He does not look 54.i thought maybe he was in his early 40’s he does body building and takes very well care of him self. When we meet up its always at his house we meet up four or five times a week he always texts or calls for me to come over. I hardly ever have to ask to come over. I like older guys they seem to be more on my level. He did ask me the first time we had drinks if i would ever get married again i told him im not going to say yes or no im just going to go with the flow if it happens then it happens. He then said “i want to get married again”. I said “do you” he shook his head yes and it got left at that. He does hide that we are FWB he has had other employees/his bosss comfront him about me and he denies it because he could lose his job. Im not sure if that will change since we no longer work together. The reason people at work has asked about us is because we was seen out together. Hope give you some more insite on the situation. Thanks

  2. Fuckbuddy87 // January 27, 2016 at 11:05 am //

    I forgot to tell you he doesnt call me by my name its always “babe” he has even said it a few times when we was at work. Not sure if its a old man thing or what lol

  3. @Fbuddy87…..Okay, more information is good. It’s difficult to give comprehensive answers without all the information. This new info changes our thoughts a bit. The fact that you’ve been married and have kids kind of puts you in a different category, closer to his life-stage than we originally thought, and it trumps the age difference. Also, the fact that you tell us he wants to get remarried and has asked you point blank if that’s something you want, tells us he’s thinking about it. And also the fact that you hit on him, not the other way around, changes our perception. If he had been the one to propose a FWB it would be have more along the lines of what we said in our response, but the fact that you proposed it and he agreed does not tell us exactly how he feels. Our suggestion: If you really want to see where his head’s at, let him lead for a while. We stick to our conclusion, that he feels he’s hit the lottery. Now that you’ve filled us in more, he might actually want to cash that lottery ticket in, and see where this goes. Time will tell. Keep us posted here in the comments and have fun. Any more thoughts/questions?

  4. Fuckbuddy87 // January 27, 2016 at 11:20 am //

    Thanks i will deffently keep u posted 😀

  5. Hey this pandu again..Hello guys..
    I have a ques ..
    I have pvsly told u dat my bf wantd a trendy posh partying type of girl rite….
    The thing which i recently gt to knw is …it wasnt jus some reason to escape and he literally meant it…and then i recollectd dat wen v wer together he tld many tymz dat he wantd such a type …of person..i usd to tell havn such wishes wnt last long..dnt go fr such thngs..
    One more shockn thng is my best friend also had to get seperated frm her b.f fr the same reason..he has also gvn the same reason…

    They too wer there fr 4yrs …
    Do such relations sustain..i nt mean all grls who party are bad…bt the notion or the foundation with which the relation is laid dwn is unknwn to the other girl!

  6. I found u ppl answering the other ppl ques very patiently and matter hw much i think…i fail to get an answer y guys behave lyl was jus in my case bt my frnd faced it too…

  7. @Pandu…We try hard to answer questions, but if the question is too long, or we can’t read it, or understand it, we can’t put it up on our site. Even here in the comments’ section, we won’t respond if we can’t understand it. That said, we understand what you’re saying in your question. Our answer: He may want that type of girl, he may not not. To us, it just sounds like an excuse, or an easy way to tell you that he doesn’t see a relationship happening between the two of you. We’re sorry. He doesn’t sound like he’s ready to settle down, and he knows a “party” girl probably won’t care.

  8. Thank u for ua reply ..n im sorry fr the inconvinience i brought up vth the long msg..

  9. @Pandu…..It’s no inconvenience at all. That’s what we’re here for. We truly do want to help if we can. Honestly, we just couldn’t understand your question at first. Do you have any follow-up questions/comments? We are sorry that you’re hurting.

  10. was very kind of u to reply fr my msgs..thank u so much
    I jus want to knw..y do guys feel they want sum1 who is trendy..partying..drinkn…all that type..wen they have a person who treats hm lyk a king??

    I have seen soo many ppl wanting that…i was actually shell shockd wen by bff relation also broke fr a similar reason!

    They shower soo much of love and affection…seriousness towards them…PDA….
    Do such relationships suceed? Y are guys like dis..

    I jus want to knw da answer because there are many lyk me…havn this ques…

    Do relations built on such foundation suceed?or even thru cheating suceed?

  11. Hello guys..
    It was very kind of u to reply thank u..

    I jus wantd to knw wat does actually goes in the head of the guy…with which he feels lyk leaves a girl jus because she is nt of a partying type…

    After the break up of my friend i realised that there are many guys lyk my bf…i wantd to knw..y do they thnk lyk dat…
    They stay fr 4 yrs and later the gal dat she is nt of his type..

    Y do they say that?they gv ample amount of emotionl trauma wen they are there in the relation..and in the end..they blame fr being unhappy..nt being of der type..partying ..mney..

    Wat actually goes in their head?

  12. @Pandu…..Not all guys are like this. Sounds like you are dealing with guys we refer to as “Players” or “Playahs.” Question: How old are these guys you are talking about? What country are you from? (We weren’t sure.) How are you meeting these guys?

  13. He is 23 nw!im frm india..hez my 11th standard classmate…he proposed me wen i was in my 12th ..out of fear of being played i neva accepted…bt later i thought i had a wrong notion abt hm..and then v gt commited…
    Bt it nw seems i was initially right!

  14. His friends afta da brk up told me..dat hez cannot stay commited fr long…
    Datz y i startd wndering y do guys b lyk dis..i mean..even wen everythn is correct!
    I fear he myt have to sumthn bad to learn frm such thngs!
    He always usd to say..i want a partying who shares a beer vth me…

    I keep telln hm such thngs dnt sustain…he doesnt listen

  15. Hez running in this new relation…very fast!!
    He usd to have dat fascination…my girl is trendy and flaunt type..n i neva of such sought..i was a simple girl..he knew this frm da start…
    Even then …i gave my everythn of hw much ever i cud..i was literally soo patient even wen he usd to scold me..anythn..

    When he cheated on me da 1st tym..he confessed it all by hmself and said he wnt repeat it…and he wud b trust nw afta da brk up i gt to knw dat he was straying again since 1 yr wen v wer in a relation..
    Nw dat grl is a partying type woman..

  16. He always usd to say ua better off as a wife dan a gf!!
    It usd to hurt me soo neva said anythn..
    With this brk up i jus my self esteem hit so badly…i changed myself soo language slang..i started non veg fr hm…nw i get this!

    I get a feeln is der anythn wrng vth me!

  17. Sorry typed too much..frankly reveald all of it

  18. @Pandu….Were the two of you having sex? It’s possible, what he means by a party girl, is a girl who will have sex with him. Also, 23 is very young for a guy to commit to a woman. Guys take much longer to mature. You’ll have better luck with a slightly older guy, but not too old. Late 20s, early 30s perhaps. In general, this guy is not worth your time and energy. Time to move on and look for a more mature guy. Maybe try to meet someone through an educational class, or some other way. Maybe your friends know of a nice guy.

  19. Ya v usd as faar as i knw..i thnk he wantd to cross the level..which i neva wantd…a part of me at tymz feels dat…sex myt b da reason.
    Im pretty conservative and beleivd in the institution of marriage so neva let it cross..
    Thank u fr ua valuable advice it means a lot!thank u

  20. @Pandu….You are welcome. A few things. Have you read any of our e-reports? You might get some useful info about guys there. Also, we hope you’ll let your friends know about us. We do our best to answer as many questions as we can. Just have them keep in mind that we get so many questions that we can’t possibly answer all of them. Unless they choose the Private Answer option which comes with a guaranteed response. (For a fee of course.) Anyway, we wish you all the best.

  21. Ya vl definately tell my frnds..n thank was sheer luck dat i found this site…i really wantd to knw..y guys thnk and b lyk dis…
    Thank u soo much again

  22. Fuckbuddy87 // January 31, 2016 at 10:40 pm //

    Hey Guys a little update. I went to my bosses house last night after we had some drinks out. We both was feeling pretty good. He asked me “how would ur family feel about u dating or seeing someone older?” i told him they already new and they told me to do what made me happy. He then asked “how do u feel about it?” i said i wouldnt be here now if it bothered me. I also told him i hated hiding it and he said “then dont”. He also gave me kiss afterwards if u get my drift lol hes never done that before. Im asuming he wants to cash in that lotto ticket lol im hoping it wasnt the drinks talking but what do u guys think?

  23. @Fbuddy87……We think you should stay the course. Keep letting him initiate. Question: He says you shouldn’t hide the relationship anymore. But is he? Just curious. And explain your work situation again. You used to work together but now you don’t?

  24. Fuckbuddy87 // February 1, 2016 at 10:08 am //

    No we no longer work together its been about two weeks since i worked there. He did tell two of his buddies about me. He asks for me to come over every night. He even told me weather its night time or day time i was welcome to come over.

  25. Fuckbuddy87 // February 1, 2016 at 10:40 am //

    One of the buddies i didnt even know about him so it was a surprise for me to know that he new about me.

  26. @FBuddy87…..One thought. Yes, you should let him initiate for now, but at some point, if you want more of a committed relationship you might need to talk with him about it. Right now, he’s getting his needs met and it’s all good, but you might not feel great about it in a few months if things stay as is. Something to percolate on. Stay the course for now.

  27. Fuckbuddy87 // February 2, 2016 at 2:00 pm //

    Its funny u said to talk to him because i flat out asked him today if he wants to hide us or not because i want a real answer without drinks involved i will u know what he says

  28. @Fbuddy87…..Keep us posted.

  29. Fuckbuddy87 // February 3, 2016 at 2:41 pm //

    Hey Guys i never got a answer to my question. He never responeded so i decided to back off completely im not going to text or call him im going to wait for him to contact me. At first im not going reply or answer him. The last time i done this he texted me telling me he missed me.(this happen like the 2nd month we started fwb) i will tell u he doesnt like talking about his feelings in anyway unless hes drunk ive even said this to him at one point and he agreed with me.

  30. @FBuddy87….Sounds like a plan. However, keep in mind. Just because he doesn’t like talking about his feelings doesn’t mean he can avoid your question. If he avoids your question then you have to decide how to interpret his silence. Typically, avoidance means a person’s afraid to speak the truth. But let’s not jump the gun. For now, just wait and see. Maybe he’s gathering his thoughts and will contact you soon. Hopefully.

  31. Fuckbuddy87 // February 6, 2016 at 1:48 pm //

    Hey Guys he finally contacted me. He asked me to come over so i did he told me that he dont care if people out side his job knows about us. With that said we both know that there are a few people at work who do know about us. He said he wants to keep his job as professinal as possible. Which i can understand. After talking we got busy if u know what i mean. While getting busy he said “my(body part)is yours you can have it when ever u want.” Then he wanted me repete it back to him. So i guess thats a good thing?? I didnt leave his house 11:30am ive never stayed that long partly my doing. We stayed busy off and on from 12am to 11:30am which is about 4hrs more than usual.

  32. @Fbuddy87……It’s nice that he contacted you, but tell us again exactly what you want from this. If it’s just hooking up, then this is all good. If you truly want something more, he should take you out on some proper dates.

  33. Fuckbuddy87 // February 7, 2016 at 10:57 am //

    Im happy right where we are for now i am technically still married and its going to be a few months before my separtion is final. I think i just want to just see where it goes from here over the next few months i have a lot of changes going on in my life and until its all figured out i really shouldnt be in a relationship not saying i dont want to be its just that i think its best right now.

  34. @Fbuddy87……Okay. Have fun.

  35. Fuckbuddy87 // February 7, 2016 at 5:10 pm //

    Thank you!

  36. Fuckbuddy87 // February 14, 2016 at 12:04 am //

    Hey Guys i have a new question. My fwb wants to add another women to the mix. He said “i want to take are sexual relationship to a new level” he asked me to go down on another women while he is pleasing me. He said he doesnt want to do anything with her just wants me too. He asked if i wanted him to pick the girl or if i wanted to pick. I dont know how to take it. I feel like we had a good thing going and now its going to be ruined im not really into the ideal of it. I feel like im gonna have to walk away from a good fwb. What do i do?

  37. @Fbuddy87……What you don’t do is something you don’t feel comfortable doing or don’t want to do. What’s happened is that your arrangement is kind of like an addiction for him. For example: When someone starts drinking it doesn’t take much to get them a buzz. The longer they drink the more tolerance they build and the more it takes to get the buzz they’re looking for. This seems to be happening here. It’s not enough to just have you, now he wants to add more to the mix. Soon it will be something else, and something else, which is of course the reason we’re not fond of the FWB arrangement. We can’t tell you what to do, but you should give this some serious thought. Doesn’t sound like you’re into it.

  38. Fuckbuddy87 // February 14, 2016 at 7:46 pm //

    I feel like he’s becoming possessive which may not be the correct term but let me explain why i feel this way. (This happened the same night he told me he wanted to take are sexual relationship to a new level.) The day before i texted him and asked if he would be busy that night. He said he was busy so i went home and went to bed my phone was on silent. Around midnight he texted and asked if i was still out i didnt reply because i was asleep and my phone was on silent so then he calls twice. I never replied to him.(i always reply to him except that night) the next day i text again around 8pm and asked if he was going to be busy he instantly replied no and for me to come over so i did. I get there and he brings it up. He said was u sleeping with someone else last night?(he says he dont care if i am) I replied no my phone was on silent and i went to bed i wasnt expecting to hear from u. So we get to business then he says “next time i call u better answer my call!” in a demanding tone of voice. Then says “I wanted this damn (kitty) nice way of saying it So damn bad i had jackoff thinking about you You better not make me have to do that again when i call, u answer. After saying that he went on to asking me if i wanted to pick the female or if i wanted him too. I told him i would just because i was blowed away by the way he was speaking to me. I wasnt try to have a conflict while getting busy. I havent been back since or even texted him. Im kind if worried that he might become controling/possessive of me. What do u think?

  39. @Fbuddy87…..He is getting possessive. Please be careful. Not to get you worried, but he’s beginning to cross the line a bit. Of course, you’ve said before that this is kind of how he talks to you. Right? We’d suggest you take a step back and really assess what you want to do. What do you think?

  40. Fuckbuddy87 // February 15, 2016 at 4:38 pm //

    Yes he has talked to me this way before. I agree i need to take a few steps back.

  41. @Fbuddy87….You shared some of the things he’s said to you, but this past conversation seemed different to us. Like you said, more possessive. Slightly angrier to us. Good that you’re taking a few steps back to assess and figure out what you want to do.

  42. Fuckbuddy87 // February 16, 2016 at 11:33 am //

    Yes its like hes done a complete 360 im not sure whats that about.

  43. Fuckbuddy87 // February 16, 2016 at 11:49 am //

    The only thing i can think of is back when i asked him if we was keeping things on the down low he also said “whats this you wanting a relationship?” but before he got the word relationship i cut him off and said “the word relationship never came out my mouth now ur putting words in my mouth”! He then grabbed his phone and relized thats not what i said. He instantly dropped the conversation.

  44. Fuckbuddy87 // February 19, 2016 at 11:53 am //

    Little update i havent seen him in a week hes been texting more than usual. He never text unless he wants me to come over. Now hes texting things like ” how have you been doing?” hes never texted asking me how i am. i havent been replying as soon as he text like before now i wait til the next day or hours after getting the text. I actualy ran into him and i avoided him. I sent him a text later just saying i was busy and couldnt stop and talk. Hes been trying to get me come over but i act busy. Im probably going to go over this weekend just to kind of see how he acts. I will let u guys know how that goes.

  45. @Fbuddy87……Ok. Just be….hmm…not careful per se…..just open-eyed and aware.

  46. Fuckbuddy87 // February 21, 2016 at 1:30 pm //

    Update i went to his house friday night we went and had drinks. The night was going good. He told me he bought me something and it was at his house. We finished drinking and went to his house. We done are business and went to sleep we got up at 11:30am we got dressed then all of a sudden his phone starts blowing up. He starts paceing back and forth and looking out the window i said “your girlfriend coming?” he said “no my stalker” i said do i need to go to my hiding spot and i lol. He said yes at this point shes knocking on his door. I go up stairs he lets her in the yell for a min and she leaves. I come down stairs i laugh and smiled at him and left. This is not the first time this happened but this the second time. The first time it was when we first started talken. We been fwb for almost eight months now. I knew something was up so i texted him last night and asked if i could come over or was he going to be making up with his stalker? He didnt reply i had a few to many shots of tequila and called he didnt answer but then he called me back i answered he said that i wore him out the night before and he was going to bed and he was going to church the nexted day. I called him a hipocurit and said have fun with your girlfriend and hung up on him. So now im pissed cuz he lied im drunk as hell i get pissed and go to his house the girl that was there that same morning was there. So i start blowing my horn like a crazy woman lol lol and i walk up and flatten his tire. Then walk up to the beat on the door i then step back because i new he would look out the window before he answered the door. As soon as he looks out he walks to the door as hes going to the door i walk back to my car. He walks out on pourch closes the door behind him. I start cursing him and tell he better not hit me up no more. And i leave. So thats the last of it i would have never done any of that if i wasnt drinking i dont regreate it but i know i wouldnt of acted that way if i was sober. Im done for good im moving on. End of story!

  47. @Fbuddy87……Okay. Well now you know. Thanks for the update. One thing: Might be a good idea not to go over there when you’re drunk. We don’t want you to get in trouble. 🙂 Take care.

Leave a comment

Your email address will not be published.

Maximum comment length is 1500 characters.