Escort keeps asking me to bottom (I'm a top)

[Wolfer]

I need a reality check. Why? Because I tend to get all worked up in my own emotional overreactions to triggers that aren't actually all that big to begin with.

 

So! Facts! A couple of weeks ago I had a pleasant session with a very hot guy. Easy to drive to (this is actually important to me), very professional and physically completely and absolutely my type.

He advertises as versatile in his ad and I had told him I was a top to which he responded he loved men who were tops. Then during the session he gets the condoms out and he asks me "You're not a bottom?" and I say "no" and the rest of the session continues with him bottoming for me.

 

Alright, so the session was pleasant enough to book a second one a couple of days later. The same thing happens "You want to bottom?", again I say "no". Rest of the session is again very nice and pleasant. Afterwards he sends me a text, asking how the session went and also adds the question: "Is there something else you'd like to try? Do you bottom?" My response was: "I don't know what I'd like to try differently yet, I'm only just beginning to explore my own sexuality." To which he responded: "Alright, boy, but I think you'd love getting fucked."

 

At this point I didn't think any of it, I just thought he wanted to help me explore my own sexuality?

 

I booked a longer multi-hour appointment with him then because I really enjoyed the sex with him. Same thing happens, he gets out the condoms and asks "You want to bottom?". I say "no" and the sex is great.

Then, afterwards during pillow talk the escort says he's actually exclusively a top in his private sex life, but that he thinks it's important as an escort to offer versatility as part of the service.

 

Hearing this made me feel extremely uncomfortable, because in hindsight, it suddenly felt as if he was trying to push me to bottom for him because he might not necessarily enjoy bottoming himself, you know? It's really been on my mind since I've got an overnight booked with him in a couple of weeks.

 

I did text him after that session, asking him if he realized he'd asked me to bottom every time now and that that made me feel very uncomfortable to the point of almost feeling like I was being pushed to bottom. I also said that I will let him know on my own time if and when I would like to bottom.

He has not responded to this at all (he did respond to a separate, unrelated question that I send along with that text)... Was it too much of me to hope to at least get something like "I'm sorry I made you feel uncomfortable, this was not my intent."?

 

I have to say, though, that I was unable to detect any reluctance or non-pleasure on his part when he was bottoming for me. He seemed to actually get into it... So I'm confused. Reality check, please. Am I overreacting?

[seaboy4hire]

Soubds like you did a good enough job communicating that you are a top. I understand that sometimes on a rare occasion a top may want to flip but it sounds like you were pretty clear you are not a bottom. To me it seems he isnt being respectful of your boundaries. What you do next is up to you. Personally if one doesnt respect my boundaries they get dismissed and I move on.

 

Hugs,

Greg

[mike carey]

Wolfer, I take it by the way the two posts were written that this is not the sexy Latino who flipped you over and played with your arse in the last couple of days? Either way there is an interesting tension between your posts in the two threads. Here you are resisting bottoming for this guy and there you were exploring the idea of bottoming. I can understand that you might not want to be pushed into it by this guy but nevertheless it appears you are considering the idea of bottoming in general even of not yet with him. I can also understand that you might be reluctant to start bottoming for him in case once you have done it one time, he will stop bottoming for you. It sounds like you enjoy your meetings with him.

 

I'm a bottom so I can't think this through as if I were in your shoes. If I were with an escort who kept pushing me to top him I'm not sure what I would do (performance anxiety aside), although I do think my hypothetical situation of being a reluctant top is less challenging than yours as a hesitant bottom. Either way I'd rather do it with an escort who knew what he was doing and wanted to make it enjoyable for me than with a random hook-up.

 

From what you've said, you haven't said it ain't gonna happen, just that you will let him know if and when you are ready to try. So, since this guy is not asking you to do something you never intend to do, it comes down to the dynamics of your professional relationship. You have sort of left the door open for him to ask again, although he really shouldn't ask every time. Good luck with working out whether the good sex you have had with him so far is worth dealing with the requests for you to be the bottom when you are not yet ready!

[Wolfer]

Wolfer, I take it by the way the two posts were written that this is not the sexy Latino who flipped you over and played with your arse in the last couple of days? Either way there is an interesting tension between your posts in the two threads. Here you are resisting bottoming for this guy and there you were exploring the idea of bottoming. I can understand that you might not want to be pushed into it by this guy but nevertheless it appears you are considering the idea of bottoming in general even of not yet with him. I can also understand that you might be reluctant to start bottoming for him in case once you have done it one time, he will stop bottoming for you. It sounds like you enjoy your meetings with him.

 

I'm a bottom so I can't think this through as if I were in your shoes. If I were with an escort who kept pushing me to top him I'm not sure what I would do (performance anxiety aside), although I do think my hypothetical situation of being a reluctant top is less challenging than yours as a hesitant bottom. Either way I'd rather do it with an escort who knew what he was doing and wanted to make it enjoyable for me than with a random hook-up.

 

From what you've said, you haven't said it ain't gonna happen, just that you will let him know if and when you are ready to try. So, since this guy is not asking you to do something you never intend to do, it comes down to the dynamics of your professional relationship. You have sort of left the door open for him to ask again, although he really shouldn't ask every time. Good luck with working out whether the good sex you have had with him so far is worth dealing with the requests for you to be the bottom when you are not yet ready!

Correct, they're two different escorts. The tension comes from the fact that part of me just absolutely loves to top, top, top and never wants to stop, but another part of me does find the thought of getting railed incredibly hot. The problem in this particular instance isn't so much my resistance to bottoming, but more the way he kept bringing it up that also left me wondering whether he'd enjoyed our previous sessions (since he says he's top only in his private life) and therefor maybe tried to push me to bottom for him.

And also that he didn't respond in any way... I don't know, I'm a (sometimes overly) sensitive guy.

 

Add to that I've got quite the stubborn and rebellious streak in me, so the more I feel like someone might be pushing for me to do something, the more I resist and even push back. So even though I'm open to the idea of bottoming, the way it's been brought up in this case has left me resistant to try it with this particular escort.

[mike carey]

Add to that I've got quite the stubborn and rebellious streak in me, so the more I feel like someone might be pushing for me to do something, the more I resist and even push back. So even if though I'm open to the idea of bottoming, the way it's been brought up in this case has left me resistant to try it with this particular escort.

I thought that might be the case! Do you want to keep seeing him? Maybe tell him you're thinking about bottoming but the fact that he keeps asking you is a complete turn-off, and if you do bottom it sure as hell won't be with him unless he backs off. Only you know what the balance is between the things you like about him and your resentment at the way he is pushing the issue. As I said before, if it were someone trying to persuade me to top, I would have similarly mixed feelings.

[+ Gar1eth]

Ok so I'll answer for the tops ( and a top who has no intention of ever bottoming). Considering the fact that you've seen him within such a short time period, I doubt he would have forgotten what you had said. So unless you sounded 'wishy-washy', ie not resolute in your response, I might begin to get pissed/annoyed at him repeatedly asking.

 

I think though that his repeated questioning might very well reveal his own mental discomfort-cognitive dissonance with bottoming even if he physically enjoys it. This guy apparently sees himself as a top. He may have to justify bottoming to himself by always testing/asking his clients whether they wouldn't really like to try bottoming for him. It very likely is a way for him to try to maintain control over the situation.

 

Another possibility is that the majority of his clients do bottom and he either has such pride in himself as a top or he believes that all his top clients deep down really want to bottom for him

 

Now my answer might be different if during foreplay you make mention of what a nice tallywacker the guy has and you tell or ask him anything that might give him hopes that you would like to explore bottoming.

 

 

I'm not sure how comfortable I'd feel having an overnight with this guy. I'm not saying that an escort has never asked me if I want to experience the 'joy' of bottoming. (Being very small in the tallywacker department myself and with most of the escorts that I've hired being either relatively or in actuality HUGE compared to me, it's not unusual for me to wonder out loud about what it must be like for other clients to bottom for him). But unless the question is asked in a teasing manner, again I'd probably be annoyed. I wouldn't be surprised in an overnight meeting if he tried to get you to bottom/makes mention of it more than once.

 

Gman

[Rudynate]

So I'm confused. Reality check, please. Am I overreacting?

 

It's weird. Good sex, everything is pleasant and yet he's being insensitive on this one issue. In a way it sounds sort of sexy - "Oh, come on, please, I really want to. Don't you? Why not?" It could be kind of flattering that he wants to get inside of you so bad. But, I understand you're uncomfortable. It doesn't seem unsoluble. I think, I would say something like, "No, and I don't want you to bring this up again." And If he does, he's history.

[Wolfer]

Another possibility is that the majority of his clients do bottom and he either has such pride in himself as a top or he believes that all his top clients deep down really want to bottom for him

I was thinking something along side these lines... Apparently I come across as a bottom to many people. I think it's based on disgustingly offensive stereotyping, to "know" someone's sexual position by way of how they act, but it is what it is and people do it.

I don't come across as very domineering nor dominant, although I actually am both to a very high degree. I'm just aware that being overtly dominant can be quite unpleasant for other people, so I just reign it in or excert my dominance in more subtle ways.

 

Now my answer might be different if during foreplay you make mention of what a nice tallywacker the guy has and you tell or ask him anything that might give him hopes that you would like to explore bottoming.

Nope, from our very first contact, "I'm a top" has been my only and all communication about this. Only after our last session did it come up, after I was complaining to him that I had a hard time finding escorts that bottomed, because many of them seemed to be top only. This is how eventually the conversation turned to him being a top in his personal life and me having given thought of maybe trying bottoming in the future. But he had already been asking it every time before this conversation happened. We haven't actually spoken since.

 

In a way it sounds sort of sexy - "Oh, come on, please, I really want to. Don't you? Why not?" It could be kind of flattering that he wants to get inside of you so bad.

I hadn't thought of it like that before. Though the way he asked it was almost off-hand and throw away like just: "You bottom?" and the rest of the session then happened as if the question had never been asked.

I have been complimented on my ass a couple of times by escorts. I do have a very big butt and apparently it looks quite fuckable. Hahaha, so there you go, I guess.

[Rudynate]

You h

 

I hadn't thought of it like that before. Though the way he asked it was almost off-hand and throw away like just: "You bottom?" and the rest of the session then happened as if the question had never been asked.

I have been complimented on my ass a couple of times by escorts. I do have a very big butt and apparently it looks quite fuckable. Hahaha, so there you go, I guess.

 

It might take a little embellishment.

[mike carey]

Wolfer, talk to him, tell him what you want to do, if you don't agree, move on!

[+ Lance_Navarro]

In my work I always want to meet the client where they are comfortable, while at the same time encouraging them to explore the unknown and face their insecurities and/or fears. I usually wait until the second or third session to start encouraging this "push", but I'm always mindful to not push too hard and violate their trust. If you are interested in a little bottom exploration, just not getting fucked, maybe tell him that a little finger play and prostate massage would be an option. If you aren't ready for any of that, than tell him that. If he doesn't repect that, than you should move on. I do encourage all to explore their versatility, but it's an individual's choice whether to and when.

[+ purplekow]

While being asked again and again might be annoying, it certainly does not seem to be a deal breaker. He asks, you say no and you move on and wind up having a great time. It seems to me you have found an escort with whom you can have a great time so I would focus on that. Next time he asks, say something like "still a no" On the other hand, since you have been playing with the idea of bottoming, may be is sensing that and is acting on that. The fact that he is a top who bottoms for you may speak to his desire to top you or it may be that you are sending out a different message with your body language than you are with your words. You say no no no but your eyes say yes.

[+ Truereview]

Ok, maybe I'm just an a-hole, but to me, regardless of how pleasant an experience is, if someone repeatedly ignores or forgets details that matter to me, I'm dumping their ass. And this is NO small detail! Also, ignoring your specific text on the topic but answering part of a related note is so odd . I would say if you were dating him, it would be worth all this effort...ultimately, you are PAYING this guy to deliver a service. Would you go back to a restaurant that insists on serving you the special when all you want is the prime rib?

 

Wolfer, I would also recommend you put all your energy on Fabio - your other advice thread on bottoming. Fabio sounds like a keeper. I may just have to head to Brussels in the Spring to test him out

[+ purplekow]

Ok, maybe I'm just an a-hole, but to me, regardless of how pleasant an experience is, if someone repeatedly ignores or forgets details that matter to me, I'm dumping their ass. And this is NO small detail! Also, ignoring your specific text on the topic but answering part of a related note is so odd . I would say if you were dating him, it would be worth all this effort...ultimately, you are PAYING this guy to deliver a service. Would you go back to a restaurant that insists on serving you the special when all you want is the prime rib?

 

Wolfer, I would also recommend you put all your energy on Fabio - your other advice thread on bottoming. Fabio sounds like a keeper. I may just have to head to Brussels in the Spring to test him out

If they insist I have the special I would not go back. If they suggest the special, well that is a courtesy. It may be that they know their product and want the patron to have the best experience that he can. Sometimes what we want is not actually the best choice.

[+ Truereview]

If they insist I have the special I would not go back. If they suggest the special, well that is a courtesy. It may be that they know their product and want the patron to have the best experience that he can. Sometimes what we want is not actually the best choice.

 

Ha! Good point, PK! I am a sucker fo gentle prodding

 

I'm curious, would you go back if you had told your regular server "don't offer me the special again, I will let you know when and if I want it" and then the server blew off you comment? I wouldn't...lots of fine restaurants out there...even if I have to drive a little longer

[+ purplekow]

If the food is good (according to the OP the sex is good) and the server was otherwise diligent in his attentions to my needs (the escort is bottoming like a champ) local ("he is easy to drive to and this is important to me) and I really had been considering the special (Beef Stroganoff though I am for now a ham eater) and he did it politely and professionally without any sense of pressure (it is only in hindsight that he even feels as though there is an issue) then yes I would go and would order what i wanted and I would eat it vigorously sloppily and happily and I would be sure that it was known just how much I enjoyed my meal and that though the beef may be great the pork is even better. And by the time I had enough pork, and I really did want the beef, the server would say: "But sir, I love the gusto with which you devour that pork, are you sure you want the special"

[+ Truereview]

If the food is good (according to the OP the sex is good) and the server was otherwise diligent in his attentions to my needs (the escort is bottoming like a champ) local ("he is easy to drive to and this is important to me) and I really had been considering the special (Beef Stroganoff though I am for now a ham eater) and he did it politely and professionally without any sense of pressure (it is only in hindsight that he even feels as though there is an issue) then yes I would go and would order what i wanted and I would eat it vigorously sloppily and happily and I would be sure that it was known just how much I enjoyed my meal and that though the beef may be great the pork is even better. And by the time I had enough pork, and I really did want the beef, the server would say: "But sir, I love the gusto with which you devour that pork, are you sure you want the special"

. Last question, do purple cows really like beef stroganoff, ham, pork? I'm hungry all of the sudden!

[Wolfer]

I'm vegan, you guys.

But thanks for the helpful comments!

[TruthBTold]

Wolfer - vegan or not, you mentioned that you have great sex with this guy and that you really have been thinking about bottoming. Is there any other reason than his semi-badgering whether you want to bottom that keeps you from doing so with him? For example, for me, in some cases physically some people aren't the ones that conform to my idea of who I want to top or who I want to bottom for me. If, however, he meets your physicality test, you simultaneously have to feel that he will do the things you want when you begin your bottoming experience (e.g., you may want to start out by straddling him). But his behavior so far shows that he will follow your directions and preferences (e.g., I do not want to bottom now.) If I were you (and of course I'm not) I would forget about his slightly annoying questioning and whether he got back to you or not because, as others have pointed out, you will never know why he is asking you to bottom every time he sees you (you must have quite the bum ) or doesn't answer your directives about bottoming. On the other hand, if he is a guy you would like to bottom for If you try bottoming and you love it then you have a guy who seems to give great all-around sex. If you don't like it you can tell him that you discovered you do not like bottoming and will never, ever try it again. I have a feeling he would never bring it up again. At that point, if he brings it up, I would move on.

[Zapped]

This is interesting! It's possible that he's picking up on your wanting-to-bottom energy, even if he's also turned on by you and would love to top you. A lot of escorts would in a different culture be more cleary understood as the sexual healers and erotic guides they are. I know you love topping, and want to stay in control, but does it resonate for you at all that he could be gently leading you in the direction your "inner bottom" wants to go?

[+ purplekow]

. Last question, do purple cows really like beef stroganoff, ham, pork? I'm hungry all of the sudden!

Who doesnt love some hot porking? As for me, I am a beef strokin' off, sorry, Stroganoff fan. When people ask" Where's the beef? " I say: " I am right here Stroganoff." I sometimes get the reply that I am too much of a ham to be beef, but I happen to be able to channel my inner pig and I think that is a good thing.

[+ Truereview]

Who doesnt love some hot porking? As for me, I am a beef strokin' off, sorry, Stroganoff fan. When people ask" Where's the beef? " I say: " I am right here Stroganoff." I sometimes get the reply that I am too much of a ham to be beef, but I happen to be able to channel my inner pig and I think that is a good thing.

 

PK, consider me porked, stroganoffed, & beefed up by your meaty response!

[Wolfer]

Wolfer - vegan or not, you mentioned that you have great sex with this guy and that you really have been thinking about bottoming. Is there any other reason than his semi-badgering whether you want to bottom that keeps you from doing so with him? For example, for me, in some cases physically some people aren't the ones that conform to my idea of who I want to top or who I want to bottom for me. If, however, he meets your physicality test, you simultaneously have to feel that he will do the things you want when you begin your bottoming experience (e.g., you may want to start out by straddling him). But his behavior so far shows that he will follow your directions and preferences (e.g., I do not want to bottom now.) If I were you (and of course I'm not) I would forget about his slightly annoying questioning and whether he got back to you or not because, as others have pointed out, you will never know why he is asking you to bottom every time he sees you (you must have quite the bum ) or doesn't answer your directives about bottoming. On the other hand, if he is a guy you would like to bottom for If you try bottoming and you love it then you have a guy who seems to give great all-around sex. If you don't like it you can tell him that you discovered you do not like bottoming and will never, ever try it again. I have a feeling he would never bring it up again. At that point, if he brings it up, I would move on.

Thanks for the advice. It's true that I can't know what his reasons are, and since I'll only be able to properly talk to him during our overnight I've decided to let it rest now and just remind him at the start (or the day before) of our overnight that for now I don't want it to be a topic anymore. Worrying about it now won't change the situation anyway.

 

This is interesting! It's possible that he's picking up on your wanting-to-bottom energy, even if he's also turned on by you and would love to top you. A lot of escorts would in a different culture be more cleary understood as the sexual healers and erotic guides they are. I know you love topping, and want to stay in control, but does it resonate for you at all that he could be gently leading you in the direction your "inner bottom" wants to go?

Myeah, but I'm not even sure I've got an "inner bottom". As far as I can tell, every cell in my body wants to top, top and only top. My interest in bottoming is mainly based on the idea and fantasy that being able to get railed might be hot, but there's no actual physical or emotional desire for getting fucked. But I want to at least try, you know? At this moment it's all theory, as I have not been topped for years (and the last time wasn't great).

[Rudynate]

.

My interest in bottoming is mainly based on the idea and fantasy that being able to get railed might be hot,

 

"Getting railed," love that expression, never heard it before. It's mine now.

 

I'm mostly top, but definitely love to "get railed" by the right guy. Flipping is my ideal sexual practice.

[Wolfer]

"Getting railed," love that expression, never heard it before. It's mine now.

M'pleasure I can't remember where I heard it, but it definitely perfectly describes why I want to eventually try bottoming, mmm hmmm.