• Anal sex pain and prostate orgasm help

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    HunnyBoy [sign in to see picture]
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    Helloo, Im not sure if this is the right place to post this, but thought some people here might be able to lend some advice as there seems to be a few similar posts, thanks!


    I'm kinda young (18) a boy and new to sex in general (still a PIV virgin actually), but Ive developed a FWB thing with a really nice lady a few years older than me(33). The only thing, and its not a problem, but she doesnt enjoy PIV sex, lovely wonderful oral but.. anyways to the issue.

    She really enjoys strapon sex, I was pretty apprehensive and scared at first but I've found myself enjoying it quite a bit. Its been a few weeks since we've started getting physical, seeing each other every couple days. I was hoping the bit of pain might go away after the first couple times but it persists a bit (maybe a dozen sessions now), during its almost all pleasure, but initial penetration is a bit painful as is pooping slightly now and then afterwards. No pain when not using my bum, and its only near the entrance. She's very gentle and all that, takes her time, lots and lots of super slippy lube and we don't rush into it, she spends quite a bit of time baby-oiling, lotioning, blowing and fingering me before the sex starts.

    Its awesome and I'm always rock hard when penetration begins, I dont honestly mind the little pain, its brief and maybe she gets off on it. Realistically I know a smaller dildo in my very recently virgin bum would probably be the best, and she has a couple, but this one is her favorite so I'm inclined not to ask, I'm sure she wouldn't mind but I do enjoy the size/shape/texture too. Our sex does get a little animated at times and she puts me in all sorts of positions, Im a touch on the "petite" side and she's not, not big, just big enough to kinda woman-handle (hah) me when she gets close to cumming. She apologizes profusely and showers me with kisses and cuddles and lotion when she can tell shes gone a little too far, and I almost hope she does get a little rough because of that, its very very nice.

    So uh, large penis/dildo anal sex havers, does the body adjust after a bit or do you have any tips? Is there maybe a position that works better for vigorous/long thrusting and getting her off? Right now when she really needs to cum she puts me on all fours or laying on my stomach and goes pretty deep, then pulls nearly or all the way out then all the way back in with her pressing on my cheeks for a bit, the dildo is 8 inches or so and I think the long stroke and harness pressing on her clitorus is what does it for her. It feels absolutely amazing but it is when it can hurt a little too. Theres no allergic or chemical reactions (lube and dildo is all the proper kind and shes safe with the lotion and oil careful not to get anything but lube inside). We've discussed the pain so she knows, and we both think its worth it, at least if it doesnt get too much worse. I also want to be sure the pain isnt a sign of something unhealthy, its not her first rodeo boy-virgin/strapon wise, and shes very reassuring, shes completely mature and trustworthy as well as working in the healthcare field so its really more a matter of piece of mind.

    Oh, one more thing, shes been trying to give me a prostate orgasm, and says when it happens Ill know for sure, sometimes it feels reaaally close but Im not sure having not had one before. She's alluded to this not being a problem with other boys in the past and has ordered a couple of those aneros toys as well as a few plugs of various shapes and sizes to try on me. She also ordered a prostate attachment for her big hitachi vibrator... so I suspect I will be having prostate orgasms soon come hell or high water, but if anyone has any tips for coming while being f*cked that would be great, thanks!

    Um I think thats all, wow long post, sorry for any grammar errors and thanks very much if you're still reading! Sorry again if this is the wrong place!

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    WillC [sign in to see picture]
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    What`s PIV and FWB?

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    NatandTom [sign in to see picture]
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    WillC wrote:

    What`s PIV and FWB?

    PIV - Penis in vagina

    FWB - Friends with benefits

    Tying to think of the right words for a response to your question, will get back to you! This is a very helpful forum so I'm sure you'll be offered plenty of good advice in the mean time :)

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    Terri JJ [sign in to see picture]
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    Firstly, Hi and welcome to the forums.

    I think you already know the answer here. 8 inches is quite bit to take anally particularly if she's using it with some force as seems to be the case. It may well be her favourite and if you like the style of dildo (I'm assuming it's a relatively realistic one) then I suggest you look for a slightly smaller version of the same thing....look togther if you like, Lovehoney sell a very comprehensive range and offer a 365 day money back guarantee.... even if it's been used.

    I'm very experienced in all types of anal play/sex and I do like to feel full and really stretched but you do need to up the size of what you're using gradually to let your body stretch and adjust accordingly. If she's using you like this every couple of nights (and I don't mean using in a bad context) then your body isn't getting a chance to recover.

    It's sounds as though you're both doing the right things regarding lube etc but I just think that as the pain seems to be when she's got you face down, going for it, the dildo is a little big for you and she's thrusting too deep and too hard, at least at the moment. It sounds as though you do communicate fairly well with each other and you say you've told her the issue but you both think the pain is worth it.......I personally don't. Anal is my favourite type of sex and as I say I do enjoy being really stretched and I can take really big toys, deeply without the pain that you seem to be experiencing. Try a slightly smaller dildo and maybe not quite so frequently for a bit and see if that helps. It also maybe an idea to play anally solo for a bit if you're up for it, that way you can teach yourself to relax more and stretch yourself (using toys or your fingers).

    A prostate orgasm is something very individual to each guy, some can and some can't, no matter what is tried. If she's ordered some prostate toys would you be able to use them on your own for a bit ? That way you can relax, take your time and see if you can achieve it on your own. You can then tell her what works and hopefully yor bum won't get another battering while she's trying loads of different technique to be get you there xx

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    lmh95 [sign in to see picture]
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    Welcome to the forums.

    No experience personally of strap-on sex but wondering if the pain could be because you've gone too big too fast. Maybe take a few steps back and use the smaller dildo's till you relax into it more. Possibly try a different lube. I think sliquid anal lube is the one most people recommend on here.

    The prostate orgasm is probably on it's way soon but won't happen if you are sore as you are tensing up. It could be a case of just getting into the right position, using a smaller dildo for now and being able to relax more.

    As for cumming during intercourse. Have you tried giving yourself a hand job at the same time? Great advice from Terri JJ above.

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    lmh95 [sign in to see picture]
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    Forgot to say. If she doesn't like PIV does she do anal herself? Has she ever tried the 8 inch dildo inside her anally? If she hasn't tried anal sex she might not realise how big that really is or how gentle you need to be when thrusting. For some people that will always be too large a dildo just like with PIV sometimes no matter how much you try it's just too big and hurts. You said you are quite petite in build so it may be 8" is too big for your body. Pain is never a good sign and a rest will probably do you good.

    It's a delicate area and easily damaged if you're too forceful. Doggy style means it's going really deep and vigorous thrusting could cause small tears in the skin. It might be worth trying spooning instead and if she could let you do the driving so that you are backing onto the dildo and controlling how deep it goes but definitely go for the smaller size.

    I cross posted with Terri JJ and noticed when I edited that she had given you excellent advice especially about playing on your own with no pressure to get to know what you really like.

    Good luck x

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    LeilaK [sign in to see picture]
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    Hi welcome to the forum :) I've never had anal sex, but I love anal play. If ever I use a toy and experience any kind of discomfort I stop. You definitely should not be experiencing pain, this is your body's way of telling you something is not right. I suggest you go with the excellent advice from TerriJJ and get a smaller dildo and work your way up in size. Ask you lady friend if she could be a bit more gentle with you.

    Good luck x

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    Alicia4Ever [sign in to see picture]
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    Hi

    Anal sex can be really good, but it takes a while to get used to, and as others have said 8" is quite big especially to start on.

    It's not my intention to be negative here but your relationship with your FWB concerns me a little, especially as you say she has done this with other virgin boys before. I know you are 18 and a virgin so sex is new and exciting, but please don't take a few kisses and cuddles as payment for pain you suffer. This all seems contrived and controlling on her part, some thing she can get from a yound lad that older men would not stand for.

    You know your own mind, but please step back and think about what you really want from this relationship,

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    lmh95 [sign in to see picture]
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    alone4ever wrote:

    Hi

    Anal sex can be really good, but it takes a while to get used to, and as others have said 8" is quite big especially to start on.

    It's not my intention to be negative here but your relationship with your FWB concerns me a little, especially as you say she has done this with other virgin boys before. I know you are 18 and a virgin so sex is new and exciting, but please don't take a few kisses and cuddles as payment for pain you suffer. This all seems contrived and controlling on her part, some thing she can get from a yound lad that older men would not stand for.

    You know your own mind, but please step back and think about what you really want from this relationship,

    Well said alone4ever. I also wondered how much you are actually getting out of this relationship. You are very young and easily influenced. Sex should be fun and enjoyable for both of you. It's not all about one person and their wants, needs and desires. It's teamwork. If you were my son I would hate to to think you were being taken advantage of just for someone else's pleasure and that you were being coerced into doing any potentially damaging stuff that they like and you were just going along with it to make them happy. If you have a break from strap-on sex for a while and you are still sore when going to the toilet it might be worth having a visit to your GP just to check that all is well and no damage has been done. However if you are bleeding at all when you go to the toilet or leaking any blood at all when not at the toilet then you should see probably see your GP as soon as possible in case of damage or an infection. Take care x
    1456646890
    HunnyBoy [sign in to see picture]
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    Thanks every body so much for all the answers and help and info even if people kinda say the same thing or if I've heard it some place else its really very re assuring to hear it from more than one person, please dont take it as something like "ya I know"! You're all just awesome! Sorry it took me a few days to get back here, I dont get alot of completely private computer time among lifes other activities. And please excuse if it comes off a little disjointed or I repeat things, family is pretty conservative so sometimes I have to stop mid post. Im not sure if its best to reply one at a time or with just one so Ill put the one here with sections.

    @NatandTom C

    Cool thanks!

    @Terri

    Hi, thanks! She said the same thing about the size, and really does try to be so gentle with me but sometimes ya... When we were looking at the other toys online she did click on a few other realisticy dildos like hers but I'm not sure if she ordered one, we realized we were late just then and headed out. Im still a little shy about sexy things so I haven't asked her, she tends to be the one to bring that type of stuff up, though she encourages me to ask questions. Thats pretty cool about lovehoney Ill let her know!

    Ya full and stretched is really nice.. kinda dont want her to use something smaller but yes I understand, Im pretty sure she does too. She does spend lots of time with her fingers in me before sex especially the first time, felt like hours. Its been pretty frequent yes, if we spend the day together we might do it a couple times even and if I sleep at her place we do it in the morning too, guess its kinda a new relationship thing :P She does always ask how I feel though if it hurts or is tender before and after, and massages me after down there inside and out. She also keeps ours nails really nicely groomed and short so I dont think its that either, that thought just came up though... We actually didnt get to see each other for almost a week before friday night/saturday and it was better for sure, even if it did feel like I had tightened up a little.

    That makes sense yeah, and Im pretty sure she knows, if the sounds im making go from pleasure to pain, even if she only thinks its pain, or if I move/pull away in a way she thinks might be pain she is always always very concerned and slows down/stops or pulls out and relubes. She brings up my smaller size now and then too so I think she understands why, she even mentioned she'd get a ring for the dildo, i didnt understood what that meant when I posted before but it seems to be something that will help with depth. It might come off like Im saying "ya I know uhhu" or something, I've just always kinda been one to look for a few different sources for answers so I appreciate the info and insight very very much!

    I know I said she might get turned on by the pain but I think its more just having an effect on me, I tend to be pretty quiet in general and even more so during intimate times, pretty much any reaction from me gets a big response from her. Sometimes putting "pen to paper" gets thoughts going that werent before. And I really think with the toys/ring she is trying to eliminate the pain.

    She said not to worry about it too, but at the same time I can tell me really wants me to have one, and the descritpions ive read are like wow. Would be nice to have one though even if its just for her, everything already feels so soo good.

    Honestly Im much more relaxed at her place than at home, I still live with my parents and they're kinda conservative and older, I don't really even feel "safe" masturbating when they're home. She spends quite a bit of time massaging me as well as just lotioning and cuddling me or rubbing me if we're watching a movie or talking, and thats on top of just the way she is to be around, I dont think I've ever felt so at ease. :) Im positive she would give them to me to take home though yeah, even if I just put something in in bed at night for a bit, might do that.

    Thank you very much again you're help is so nice!

    @lmh95

    THanks!

    Yeah that does seem to be the concensus about the size, Im not sure what lube she uses, its in a little fancier pump bottle thing with no labels, but she did use it with just her fingers the first couple times, and there was no pain, it does seem to be really good stuff though very very slippy.

    Im not really sore and tensing up for the most part, just at first and when shes close to cumming, its pretty much all pleasure "during" and there is a focus on relaxing me quite a bit I think. Shes even stopped a few times in the middle of a pretty good thrusting to pullout and cuddle for a bit. She has been fairly experimental with positions yeah as well as using pillows to boost me up a few cm here and there.. I didnt understand when she said wedges, but it seems like shes ordered um sex wedge pillows? So I guess that will help.

    She quite often does play with me during sex or stroke me if I get hard, but always stops short of making me have a regular orgasm until after the strapon, it does seem like it maybe helps with getting closer to a prostate orgasm.

    She has had anal sex yeah, but I maybe don't think shes tried the dildo.. She seems really aware of me being on the smaller side, her figure is larger than mine and she does have a head and a bit on me, so I think she knows I wouldnt be able to take as much as her. I know I said it in reply to Terri, but she is really so gentle and caring and concerned about my well being both physically and emotionally and when it comes to sex even more so. She just gets a little excited in the moment now and then I think.

    Im not sure if you read the reply to Terri too but I think she is getting something to help with the depth. Im not sure if she bought a smaller dildo but I think maybe not if shes getting all the toys and the ring-depth thing. We did actually not have sex for 5 days maybe? And it was better yeah.

    Ya doggy definitely feels pretty deep, she does kinda check me out back there I think for stuff like that, also feels around and asks if it hurts. We do spoon now and then and it feels really good, as well other positions where its kinda me being more active, I just think maybe she doesn't get off as well with those. If pain does persist past getting acquainted with the plug things and that ring thing, then I think we would probably use something smaller. I do like the size though, and I think she likes the non-pain effects it has on me, any gasp or moan gets a pretty big positive response from her.

    Terri's advice and input is just amazing yes its so appreciated! As is yours many many thanks! I hope it doesnt come across like Im saying I already know!

    @LeilaK

    thanks so much for the welcome and the lucky wishes! :)

    I know it might come across a certain way, but she doesn't really keep going if I'm in pain, its just getting in sometimes for the first time that time... it goes away really quick though and its pretty much all pleasure while we're having sex. She is super gentle so so much of the time(some of the other answers above I go into a little more detail), honestly I kinda like the way she is when she isn't, everything is still so caring.

    @alone4ever

    Hiya!

    Thats good to hear! She has said it gets better and it is.

    Your concern is appreciated and very touching thank you so much :)

    She asked me early on if I'd like to be her FWB, and said it was more that she realizes Im young and still figuring myself out. She isn't looking for anyone else, but she doesnt want me to feel like I cant look for a relationship with someone else if thats what I want. We also had a reeaally long sex and relationship talk at the same time so everything was kinda all laid out from the beginning.

    I was and am still really so extremely shy with girls in person or just people in general(which she has been just amazing about helping) so Ive never had any experiences with relationships at all. I know maybe I dont know... but outside of the bedroom Im not sure what more a "real" relationship would involve. She was the one to pursue me initially and I know she did because I look and act a certain way, Im completely ok with that, I am who I am at least for now, its been pretty rewarding and very uplifting especially after experiences growing up. Maybe you know.. :( its gets lonely out there... :(

    She is generally in "control" of the bedroom and other activities and the one to initiate things sexually, part of that is my shyness and inexperience, she does really encourage me to be more assertive in all aspects of life though. I know its not really what ya mean, but it doesnt feel like payment for pain, I understand that part of what must get her off is being the one in charge, or the dominant one, and right now Im liking being the other side of that.

    Thank you so much for worrying about me and all the advice, its so appreciated!!

    @lmh95 again :)

    I think maybe some of the other posts above and the first one to you might go over some of your concerns, I just want to say all this care about me has so much compassion its moving. Outside of family(sometimes) and her, its not something life has felt very full of.

    Its hard to describe how it feels, so positive... like its OK to be me, I got bullied alot especially when younger... by girls mostly... Ive been kinda withdrawn for years... I know Im young and easily influenced, on top of that I dont have a great deal of life experience even for my age. Its likely that all those feelings would be there for any first relationship I guess, but Im not so sure there would have been one in the first place if it were depending on me or other people in my life previously to get started.

    Our sex is very fun and enjoyable, as well as.. I dont know.. she makes love to me... we make love... I dont really have a word for how emotionally amazing and pleasurable it feels at the same time. I do realize how things come across though.. or maybe sometimes even are depending how things are framed.

    Im not at all rejecting what you say, the perspective is most appreciated, I really dont feel coerced or taken advantage of in any way. She does seem very careful with the strapon, and we did talk about the dangers and seeing a doctor/hospital immediately if things felt not good. I mentioned above but we did actually not see each other for 5-6 days and yeah no pain at all over that period except for a slight twinge pooping the morning after, which didnt keep going. And when we had sex yesterday/today even though it felt tighter to start it did feel a little better maybe than the last time, its really not much to begin with, so its hard to gauge how much better from time to time but from first until now its improved. She was also in me a couple times today like she has been and there was no pain the second time at all the whole way, and no poop pain just now, also no blood at any time ever.

    Once again I just want to thank all of you so soooo much! You've given me alot to think about and so much to appreciate. Im touched at the outpouring, thank you!

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