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Would You Ever Hookup with an Ex-Boyfriend?

(Photo Credits: Sean Cody)

My answer is a definite no even if I am single but that’s just me. What about you? As for the why, well, I may run the risk of falling for them all over again as Canadian pop singer and songwriter Dan Hill puts it. I loved them at some point in my life in the first place and it’s not impossible to fall for them all over again if we hookup. And if I did, and they didn’t, then here comes heartbreak.

Besides, we already broke up; as a matter of principle I always keep in mind that there are good reasons as to why we did. And although my breakups are always amicable and admittedly I remain in contact with all of ex-boyfriends exchanging hi and hello, how are you sporadically, that is all there is to it. If my other friends asked me whether I remain friends with them or not, I’ll say yes, my ex-boyfriends probably will say that, too; but in truth I am just friends with them now in spirit. The closeness is gone and I have no plans of rehashing everything, ever.

So yes, for me, parting of the ways with ex-boyfriends is final; finis, over and done with, the end. No hookups, no looking back but then again, that’s just me.

What about you, guys? Would you ever hookup with an ex-boyfriend? Why or why not? Maybe you already did? In which case how did that turn out for you? Share with us your thoughts and your hookup stories with your ex-boyfriends in the comments section below.


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  1. John

    I would. And I have. I am still close to a couple of my exes. We knew that us hooking up was just that, a hook up

  2. Bubble

    Oh well. I can. But thats because for me, sex is rarely emotional. So I can literally have sex with anyone. What keeps me with my relationships is not the sex but the personality and love we share. Sex is good though and I can have it with anyone. I strongly believe people have more sex in their head – which is unhealthy to their emotional self – than they admit in reality. Lets be real.

  3. Naturalbooty

    Yes. I have several times. And the sex was better than it was the years we were together. Just because he was my ex doesn’t mean the relationship ended badly. We remain friends. The affection will always be there.

  4. Eric

    I have and it was a mutual agreement between the two of us. We both knew that rekindling our relationship wasn’t possible and besides, he’s one of my best friends (with occasional benefits) so we established that boundary. Not every situation is the same but as far as mine is concerned, its a mutual understanding

  5. Lamar

    I have and I would again, good ole’ reliable and familiar sex, with an edge of making love to it. If you both chose well to begin with, then there’s always that element of, “we still love each other, just no longer in love.” If, when you parted it wasn’t too bad.

  6. Dylan

    Well it just so happened I was down in Miami and checked into a beach resort. Was there because my boss wasn’t. Needed some me time to decompress. I knew I’d be hooking up there but wasn’t my main reason for being in FL. I finished checking into the hotel, dropped off my bags, changed clothes into shorts and grabbed a towel as I was gong to the beach to just drink and relax.

    Wasn’t there 20 min and my neck was already sore from staring at the amazing bodies running all over the beach. I hear an “ugh-aheem” you know the sound gays make when they want your attention. I look up and it’s my Xbf and his husband. They start off and say hello, welcome to Miami, more small talk. His husband was VERY fucking condescending and snobby. I was turned off rapidly. Then he asked how long was I going to be in town? I said,”just 2weeks staying there at the resort.” He then says,”well I guess we should have you for dinner (with that rich smug I just graduated form an Ivy League school voice) only if you promise to keep your cock out of my husband while you’re here.” I didn’t know what to say. Then said,”yeah we should catch up
    I’m staying in room 1112 stop by we can grab dinner. I have no plans..” I knew my X. I planted the seed and told him where I was and what room. The next day he stoped by in beach attire (that’s fancy talk for towel and speedo). I told him he looked as hot like usual. Then walked over to him, kissed him hard on the lips and said,”damn I miss that!” Grabbed him by the shoulders and forced him down on my cock. He remembered exactly how I love to get blown. I pushed him on the bed and began to face fuck him. I pulled off his speedo and told him,” I’m fucking you, you know that right.” he said,”dude I can’t I’m married. Thad be wrong.” Long enough to pull my cocknout of his mouth to tell me. I rolled him around and ate that ass. His back arched immediately as if you were petting a cat. I stood up and slid my cock into him. It was as hot as I remembered. I fucked him for a long time. We missed the sun on the beach. But still went so he could get sand on him and in his car for proof he was at the beach. I ficked him almost daily while I was there. His husband came by one day with him and saw me at the beach. That douche said,”well since you’ve been a good boy, we are taking you out to one of miami’s finest restaurants. It was nice but I’d have relathered a Cuban sandwich from a truck. The day I was leaving my X called in sick to work and came tommy hotel. One last romp. From 5:45am until 12pm there was nothing I didn’t do to him. I made sure he was gonna walk funny when he went home. So fuck yeah I’ll do my X any time. I just couldn’t date him again.

    Oh….AND FUCK YOU RAY! NO ONE TELLES ME WHO I CANT FUCK!!!

  7. Caleb

    Contrary to all the other exes in the past, my last ex and I continue to hookup, and find the sex much better and more frequent than it was before we split. Because we continue to appear together in some social settings, I am asked if we are back together, to which I always, “No…just friends.” I did not fall out of love with him when we broke up…I am moving on but enjoying the relaxed uncomplicated great sex and companionship we are enjoying as we move into other relationships, which we don’t discuss with each other.
    Will it work itself out eventually? I don’t know. We obviously still need each other but not in the same way as at an earlier point. As with most all my friends, if they need me, I want to be there for them.

  8. Don

    No way here ! When I’m done…I’m done ! We can be friends, that’s it. I am friends with all but 2 of my exes.

  9. Tom

    Previous experience bugged me to death for sex after we broke up, and no, I’m not that good. ‘Told him he relinquished the right to this ass, cock, and mouth, when he walked out on me leaving me with $50,000 debt and a big mortgage payment. All for a guy with a bigger . . . wallet. So, no. Didn’t happen and won’t happen.

  10. Leo

    It’s a subject I’m currently debating with myself. On the one hand, the sex was good. A little too vanilla for my tastes, but it was very nice. I’ve had better since then, and at the moment, I’m grasping for something real and familiar. But I don’t think a renewed relationship can be possible. He was a lousy boyfriend.

  11. Feep2007

    I did and it just wasn’t the same. The fire just wasn’t there like before when we were together. I wish it didn’t happen.

  12. Anthony

    From many previous experiences thinking it will be a better experience every time i tried to move on and have a fresh start i would have to say , No !!!!!

  13. Art

    My ex is 6’5″ tall with dazzling blue eyes with silver not dull gray hair but is married. He was not
    really a good lover as what started out as just great sex somehow turned into a passionate affair.
    What was compelling was that he turned into my very best friend and in doing so sex turned into
    deep seeded love. We did not break up, just kind of slowly separated. I would have sex with
    him a the passing of a NY second!

  14. Torre

    No I would never hookup with my ex-boyfriends because along the way they all became such assholes that I even now regret ever having sex with them from the start. I found out that along the path of the relationship the real person that they were come out and it seems that after the sex; the personality that you were attractive too; changed and the person you found yourself not liking started to make you sick on the stomach and wished you had never met them.

  15. billyg

    Been there and done that, many times with the same guy. I kept trying to convince myself it was good and it actually wasn’t. Finally said enough was enough and broke all contact. Should have stayed that way many years ago the first time it didn’t work out, but sometimes or most times the dick has a bigger brain than the one in our real head……… BG

  16. Hunter0500

    Been fortunate enough to never break up badly with someone. So sex with ex’s, while rare, is a yes. Just a matter of frank and open discussions about what it is before hand.

  17. qbano_sato

    Been there. Did it.
    We tried to get back together after that but it wasn’t the same.
    No regrets.
    Nothing gained or lost.

  18. Latinlust69

    Been there. My mistake. The first one gave me a hot fuck the kicked me out. The next one i ended up dating again. So wrong! Fucked my ass and my life.
    There is a reason for breaking up after all

  19. Alvin and chipmunks

    These girly questions are getting stupid and stupider. How about asking , ‘Would you eff Donald Trump for $130,000.00?

  20. Randidan

    Randidan – I probably would if it were for the same reasons I did it before. However, for me it’s a rhetorical question, since I ‘ve been with my other half since fall of 1959. Yes, you read it correctly! I had a couple of BF’s before HIM; after this length of time the difference in the depth of the relationship means that I think of the others as (delightful) but temporary… I suppose we ought to get married, but it might just look silly — and we certainly don’t need to prove anything to anyone. And no kids to have it matter, so I on’t know if we will actually do it or no… 🙂

  21. Dan

    Only for sex and only with my current ex. We still have a friendship and do things together on occasion. I find it odd that he will hook up with a complete stranger and give him pleasure but won’t do so with someone he has a close friendship with.

  22. mtaabq

    Would I? Yes. Have I? Again, yes. It was a serious grudge f**k and I’m glad I did it and I would do it again.

    • Dylan

      For some odd reason I find that hot as fuck!!! Would love to know what brings you back to your x? Is he better than your bf?

      • Jeremy

        Honestly man I have a cheating fetish haha. My ex has a much bigger cock but it’s not just him. When I get home and my man is still at work I like to have a dude over and put my boyfriend’s pillow between our cocks and hump it while he’s away. He’s sleeping where another dude rubbed his junk and has no idea!

  23. PostGayGrandDad

    It all depends on the reason he is an ex. If we just drifted away then it’s possible sex could happen. If we are no longer together because the sex wasn’t that good, well, that answer is obvious. If we are no longer together because he somehow hurt me or was nasty to me then probably not, unless, of course, he’s looking to be used hard and I get to punish him. But, on second thought, no. He might like it, and that would be a reward. If we broke up because we moved away or had jobs take us to separate places, then sure, “Great to see you again let’s fuck!” If we are both in new relationships and happy in them, then a little discussion would determine whether or not it’s going to be a foursome and everybody fucks everybody.

  24. wkndcowby

    Not all of them (there aren’t that many) but there are a couple with whom I would jump into the sack again anytime. I wouldn’t expect that it would lead anywhere, except to a hot shower afterwards.

  25. Ben

    Eventually I didn’t. The problem was the sex was always rockin’ great!! It was almost every other aspect of the relationship that sucked.

  26. Pogiman

    I still do think about my ex and it’s not healthy now that I married my partner. We’ve been together for nearly 20 years. Funny thing is that my ex introduce us and been together ever since. The only thing that lacks in our relationship is sex. It good in the beginning but let’s face it. Sex with ex was much better because he has a really big cock. He said before we broke up that it was the only reason I stayed with because of that. I hate to admit it. He is right in most part. I couldn’t get enough and I started looking for more. I was fairly young and didn’t know how to commit. I had this feeling he was doing the same. It was a hard brake up for me. I will never find anyone like him. I begged him to take me back but it was too late. So with being said my current partner and now husband believe it are ok. But there is still that issue with the sex. He can’t please me that way as much. Is it wrong to think about my ex on how good it was? We’ve talk every once in awhile thru social media like on Facebook. He has his own life and with another man. He knows that I still want him but I dare not ask. Thing is he said to me when I left. “You never know we might get back together again someday”.

  27. RadicalDelusoon

    It depends on how intense the relationship was. If you both realized you weren’t meant to be because you weren’t soulmates, and decided to stay friends, then a hookup wouldn’t be a big deal. But, if one person had more feelings than the other, it could spell disaster. I think it’s easy to know if people are honest with themselves and pay attention to the signs from the other person. The key is honesty and realistic expectations. It has the potential for danger, but can also be a healthier alternative to casual, anonymous sex. Every situation is different. If there’s ANY chance that one person might have any unrequited feelings, then i suggest to avoid. But, if it’s mutually casual, familiar and enjoyable without complication, then why not?

  28. Jim

    I don’t think there is an un-nuanced answer to this question. It depends…on how old you both were when you were lovers/on what kind of a break-up you had/why was there a break-up/was the sex that good just as sex/does the sex inevitably induce a significant emotional component, etc.? It could work or could be a recipe for disaster.

    The question recalls one of the better stories I’ve read on Nifty.org. It was a roman à clef of two guys who met as freshman in college and fell in love and remained in love. Unfortunately, after they finished grad school, the job opportunities for them were such that to have their respective propitious career paths, they ended breaking up. It was a heart-wrenching tale to read and begged the question if they would get back together ever. (In real life they hadn’t. They did still love each other, apparently, but circumstances prevented it for sufficient reasons.)

  29. Fireguy

    Well as for me i did with oncce with an ex but since that one time we have not. Me personally i wouldn’t advise anyone else too you really should protect your heart and feelings because its a reason you guys broke up in the first place. Me knowing what i know now no i would never ever hookup with an ex. But that is just me though everybody might have broke up for various reasons my ex broke up with me so of course my feelings were hurt and that pain has never went away because he was my heart i truly loved him and would have done anything for him. In the end he didn’t love me the same as i needex to be loved.

  30. Jerry

    Yes, I hooked up a few times with my ex after we broke it off and yeah no lie it still felt good al the right moves. To me when we both got off it was over but he always wanted to stay over and I did not want that. He would say but this feels like a hook up only and I would say that is all it is no more no less. He would say so you do not have feelings for me? I would say those days are over and it got to the point where there was some sort of argument he would say he felt cheap and I always said this is only a hook up I do not want the drama. So we stopped hooking up it was a mistake my mistake to even start it he could not handle it. I finally just left town with no address to be found. I would say to anyone else not a good thing to do.

  31. bjjj

    I would love to hook up with a past buddy, however he turned religious and now he says no more sex. Oh well, he had a nice cock and ass.

  32. Sam

    My Ex ended our 5 year relationship via email and then called me three weeks later begging to me come over; “I just wanna get f#cked!!!” I told him I’d be there in 20 minutes. He called a half hour later and asked if I was on my way. I said “Nope, I’m not coming. SO there, you’re f#cked.” I wish I could say it was the last i heard from him but it wasn’t. What was I thinking?

  33. Greg

    Depends on how the relationship ended (and how good the sex is). Have done one-timers with exes if we run into each other at a club toward the end of the night. Have altered a relationship to a FWB situation. If the sex is hot, why not?

  34. Sky

    Have many ex-boyfriends. Can think of only one I’d have sex with because we had wonderful sex. Broke up because I was still working and he had retired at a young age and traveled a lot. He was not around as much as I would have liked, so we split up and stayed friends, but I never lost my attraction to him. To make it even spicier, we are now housemates when I am in South Florida after buying a townhouse together. Maybe some day it’ll happen. More likely as part of a threesome.

  35. Earl

    There is only one i would because he was my first true love and i hadnt been out long and was scared to death what i was feeling with him.I was an over the road truck driver and his family ran a trucking company and he want to leave everything and come OTR with me.I wasnt ready for that at the time but sure know i screwed up because now i measure most guys to him and they dont measure up he moved to the west coast and i live in the midwest and we havent seen each other in years but i would jump him in a heartbeat

  36. Denn

    Oh hell no, they are exes for a reason,( I don’t harbor any ill feelings) but with time, I am no longer in love with him( but still love him, if that makes any sense to you). Life goes on and although we are not “friends”, we are not enemies.( we don’t keep in touch and I wish him total happiness) As for the sex, to me a relationship is more than just that and that can be found almost anywhere.

  37. Stubbornone

    I never could. Although I had thought about trying to rekindle something with my longest partner ( not that there’s been that many). The sex was always good and basically we got along but it was a lonely relationship. Anyway, he passed away before that Avenue was ever explored. I’ve also remained civil and distant friends with my exes

  38. Carlos

    These posts are so fucking lazy. It’s like #Gays you ever drink water, what’s your feelings on breathing? It’s like who the fuck doesn’t?

  39. Bertram

    Yeah it all depends on how you two left. For me, it was just hooking up at first for 2 years after we broke up. It did not go back into feelings..but I felt manipulated. We hooked up on and off for two years..but I recently ended the hook up aspect.

  40. goldenloverinmym

    Yes I have and hope to again soon while back visiting this summer. I have a month to see if we can make time for aday in the sack, last time was a 3 way we had fun so no issues for me

  41. LJ

    Hooking up with your ex is fun and fine as long as you’re the dominant one (so you can control the situation) and you’re emotionally secure enough I.e. over him (so you won’t get emotionally involved again). My self imposed rule “If you couldn’t trust him in a relationship then forget trusting him as a friend!” I’ve been in 8 serious relationships in my lifetime ranging from a year to 17 years ( and yes I’m older than almost anyone who will read this) and it was the man in the 17-year relationship that did the worst damage when he stole my identity, obviously since he knew everything about me. My personal attorney’s advice has always been TRUST NO ONE! I should have listened to him.

  42. Rick

    I met my partner in Germany in 1980. We were serving in different branches of the military. 26 years later we drifted apart and separated. I then entered in a 5 year relationship. Things didn’t go so well. The old saying “You don’t know what you truly have until you loose it” was certainly true. We reunited and we eventually finally married. So now as I jokingly say “We’ve been together for 38 years with a 5 year fuckup”. But, that separation made us stronger. It made me realize what I had lost and how much I loved him. So you see, i got back together with my ex and it worked out absolutely GREAT for us. I not only love him but, I am IN love with him. GOOD LUCK GUYS.

    Rick

  43. C Scott Harvey

    I get along with my ex better now than we did married and we still have sex together because it’s so good between us we’re both kinky and we just click when it comes to the bedroom

  44. jonah

    an ex is an ex for a reason…
    we all have different reasons why we split..some good some bad some were mutual decisions..
    watever the case it ended bc something about it just wasn’t working and instead of wasting your time on familiar territory take a shot a some new stomping grounds…going backwards in my opinion is just an easy way to miss out on the blessings that the future may hold for any of us.

  45. Jay

    It happens. I’m never the messy breakup person and respect is a word thrown around a lot but if you’re consistent, crossing paths with exes is easier. Never know when you may need that shoulder when times are tough, out of town and need a place, or whatever reason the ex is back in the picture.

  46. John

    Absolutely not. I figured if I’m not good enough for them when they break up with me, then I’m too good for them now. They had their chance, and blew it. It’s their loss not mine. And i doubt i would ever acknowledge their existence. In other words, i wouldn’t piss on them if they were on fire, I’d probably laugh and walk away. Hurt me once shame on you , and don’t even think of hurting me twice. So find someone else and break their hearts .for i am done with them.

  47. Will Morris

    Currently my partner of 7 years and myself invited his ex over for a three some. We all had a good time and have become good friends. The ex knows we are soul mates, knows where my partner and I stand and has respected the boundaries. Trust is the link that makes it possible for us to enjoy our very active and diverse sex life.

  48. chapstevens

    No, I remain friends with an ex. A much younger men. He is living with another man now. They both committed to each other complete loyalty. One Fri on his day off we decided to go to lunch and back to my place for the afternoon with some wine. One thing led to another and we were naked in bed in no time. Didn’t last long his BF got off work early and came over. Almost caught!
    Not to worry, 2 weeks later he was back and we did everything and even flipped which we had never done. It was wonderful. But his guilt and remorse has since ruined our friendship.

  49. slocomfy

    Never. Had to cut off all contact with the trash he either became or hid so well. While he was a vers bottom with a hot ass ass and huge uncut cock (that I had in me from time to time. I’m vers.) That is no match for the drama and fowl things that came from his mouth on occasion at the end. Then I found out he was hiding hep c from me after I let him top me bare. Anybody here ever had someone try to own them like that? It’s a horrible feeling! NO Not ever going there again!

  50. James

    I would, and I have. 10 yrs went by after an Ex and I parted ways, completely out of sight, and communication. Reconnected on FB one day, agreed to get together, had an incredible time, and mind blowing sex. We both obviously grew up quite a bit and we found it much easier to be ourselves around each other… It quickly turned into a somewhat regular thing, but had to put the brakes on when I started to get a bit too emotional about the whole thing…. Dont have any regrets, we still stay in close contact, will likely get together again, and happy where things are!

  51. David

    Yes sadly, most people have sex in their minds before the physical act and often find themselves disappointed. Treat sex as what it is a physical association that gives pleasure.
    I have no reason not to have sex with an ex for the one reason we were never in a seclusive relationship to began with, it was all about the sex and how often I could get it!


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