Virgin Dilemma Update

Virgin Dilemma Update (Full Version)

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merrymasochist -> Virgin Dilemma Update (5/13/2006 6:18:19 PM)
Well, it's official. My friend in no longer a virgin. It was warm, playful and friendly with lots of cuddling, shared laughter and talk as well as going to it like a pair of sweaty rabbits in heat. We've both got saddle sores and silly grins. For those who would wonder, condoms were used with a small discussion beforehand as to why they were important. My favorite comment from him was "bringing you to orgasm is a hell of a lot better than jerking off." Which leads me to another question for all of y'all gents out here. Truthfully, I was expecting him to orgasm fast at the first time, instead the opposite happened. Three hours and no pop. I'm not sure if it was the condoms or nerves or possibly he's just having a hard time making the jump from masturbation to sex. He seemed to have no problem with it and was a bouncy happy camper from start to non-finish for himself. I've no problem with that so long as he's happy but it doesn't seem quite fair I got multiple orgasms to his none. How can I help him cum when traditional ways, while they feel wonderful to him, are just not getting him there? Is this something time and practice will cure and I should just let it slide for now? We are meeting up again next week and any thoughts or ideas would be greatly appreciated and most welcome. Sincerely, merry

TallDarkAndWitty -> RE: Virgin Dilemma Update (5/13/2006 6:27:00 PM)
quote: ORIGINAL: merrymasochist How can I help him cum when traditional ways, while they feel wonderful to him, are just not getting him there? mumblegift horse...mouthmumble Have him masturbate for you once you have "finished" with him. Tell him how much it turns you on to see him cum. I am sure with all of his...er....practice...he'll have no trouble rubbing one out for you. wink Then he will feel more comfotable about it, and will most likely be able to do it while interacting with you in more traditional (if that is the word) ways. Taggard

theRose4U -> RE: Virgin Dilemma Update (5/13/2006 6:29:49 PM)
I would say that if a virgin lasted 3 hours without cumming himself he was busy before you got there. I would think that days leading up and probably hours before he and rosey palm were getting close. If you were to teach him anything it might be that taking the mental stimulation he has during masterbation and including that to a lesser extent in sexual interactions is ok. Biggies don't say the wrong name and make sure to open your eyes and make deep eye contact with the real partner from time to time to keep your mind in the room. I would spend some time next weekend working on him. Teach him different positions and benefits of each. Let him try things out and find his own groove. Frankly he may just be one of those lucky guys that can go forever. Another idea if you're feeling guilty at some point would be to try oral until he's very close and finish him off vaginally.

theRose4U -> RE: Virgin Dilemma Update (5/13/2006 6:33:24 PM)
quote: Have him masturbate for you once you have "finished" with him. Tell him how much it turns you on to see him cum. Also not a bad idea. Watching him masterbate will teach you a few things about what pressures and preferences he has. by watching technique you can also learn which positions will simulate the same kinds of pressures.

MstrTiger -> RE: Virgin Dilemma Update (5/13/2006 6:43:18 PM)
Pffff make him pleasure you and when you get bored kick his ass out of bed and make him sleep on the floor hehehe. On a slightly more serious note, there are some guys who find it very difficult to “fire their porridge cannon” in any other way than to do it themselves, you should discuss it with him and find out if he has any specific kinks that might push him over the edge, or you could try and make him more relaxed. I found that I could make one of my boys who had the same sort of predicament “jettison his salty batter” by “entertaining” him in the morning when he was in that sort of half sleeping half awake stage. It was actually quite fun finding out how best to do it, I think if you look at it as a game you actually might find it entertaining. Ultimately if he is happy then you should just go with that, I would not put to much pressure on the poor boy for not being able to “come up with the goods” because it might look like you are upset about his inability to do it which will make it even harder for him.

Level -> RE: Virgin Dilemma Update (5/13/2006 6:51:31 PM)
*Oh good, you try to "cure" a virgin and end up in bed with Superfuckingman laughing....* Are you saying he didn't cum at all?? Hmm. Call him and tell him to NOT masterbate... he should have no trouble "launching the fleet" then....... or lay behind him, nibble on his neck, whisper in his ear very, very dirty things, while rubbing his cock....

TallDarkAndWitty -> RE: Virgin Dilemma Update (5/13/2006 7:09:13 PM)
quote: ORIGINAL: theRose4U Watching him masterbate will teach you a few things about what pressures and preferences he has. by watching technique you can also learn which positions will simulate the same kinds of pressures. Ha! I din't even realize I was giving away trade secrets! wink One of the first things I do with a new sex slave is watch them masturbate, for just the reasons you mention above. Funny how those things become ingrained in our habits until we don't even realize why we do them anymore... Taggard

Elizabeth7777 -> RE: Virgin Dilemma Update (5/13/2006 7:09:45 PM)
Huh. Had a short fling with an otherwise studly gentleman once who told me, "I can't come the first time I'm with a woman no matter what." Surprising, but an entirely pleasant experience for me as he'd apparently learned to not even try and that meant more for me. No problems with the equipment the second time. Thought that was an anomoly until a girlfriend of mine ran into the same situation with a new boyfriend of hers. May just be the second time is the charm. I admire your choice of charity work. [:D]

Level -> RE: Virgin Dilemma Update (5/13/2006 7:15:24 PM)
quote: ORIGINAL: Elizabeth7777 Huh. Had a short fling with an otherwise studly gentleman once who told me, "I can't come the first time I'm with a woman no matter what." Surprising, but an entirely pleasant experience for me as he'd apparently learned to not even try and that meant more for me. No problems with the equipment the second time. Thought that was an anomoly until a girlfriend of mine ran into the same situation with a new boyfriend of hers. May just be the second time is the charm. I admire your choice of charity work. [:D] merry is indeed one of the good ones, from what I see, Elizabeth, I hope the young man in question realized how fortunate he is. Level

obis -> RE: Virgin Dilemma Update (5/13/2006 7:33:35 PM)
Also, masterbation and sex feel very different (especially depending how he does it). It could just be a matter of him needing to get used to the different sensations involved. Prohibiting masturbation can help in the transition[;)]

LuckyAlbatross -> RE: Virgin Dilemma Update (5/13/2006 7:50:13 PM)
quote: ORIGINAL: merrymasochist Is this something time and practice will cure and I should just let it slide for now? We are meeting up again next week and any thoughts or ideas would be greatly appreciated and most welcome. Sincerely, merry How long does it take when he does masturbate? I wouldn't worry too much about it now- nerves can do a lot and you can't really base ANYTHING on a "big first time." He's already got the foundation that it's not the orgasm that is most important- why do anything to change that?

Kedikat -> RE: Virgin Dilemma Update (5/13/2006 8:01:51 PM)
It can take many get togethers for Me to orgasm. I have played with some, BDSM combined with sex, and not cum for several sessions. Most never had Me cum with or in them. Some guys spew in any hole. I have a connection that has to be there before I will give My cum into her. I seek one that I do wish to give My cum always. she will be the only place I put it. So she best be ready for it all the time. At the end of a long lovemaking or Kink session, or to be bent over at a moments noticed and pumped and cum in quick. But for others.......nope....not likely. Makes for very painful swollen balls.

MistressLove999 -> RE: Virgin Dilemma Update (5/13/2006 8:08:45 PM)
Wonder how many times he has gotten off since then thinking about the wonderful first time with you. Congrats on making someones first time, an awesome memory. Hope your next encounter is just as rewarding, and the next, and the next, etc. Also, what kind of damn condoms where they???? LOL, maybe I should buy some of those to have on hand.(just kidding). Might ask him to not masterbate a few days before your next time, it may make him be able to cum easier with you.

xxmstrchasxx -> RE: Virgin Dilemma Update (5/13/2006 9:31:09 PM)
I really wouldn't worry about him cumming. I have always been able to control my climax and can do it when I want or not do it at all. Makes my sub happy! Of course, in his case, it might have been nerves and he'll be fine the next time.

shygirldesires -> RE: Virgin Dilemma Update (5/13/2006 9:57:56 PM)
OK maybe i am plain out of the loop.... but when i read the OP's post, i thought i was reading about a Mistress and her subby boy and wondered how old they each were.... so i went to the OP's profile expecting to see Mistress aka Domme or Switch and found well adjusted, happily masochistic submissive who enjoys pain, pleasure. Now granted i am not in the loop about masochists and their needs wants desires but as i read the OP's post, i scratch my head....was that a subby boy? or Dom? As the OP seems to be the one in control or is this what masochistic subs do? Top fromthe bottom or am i just reading REALLY wrong?? Then again, if the OP is 38...how old is the male ? i have NO issue, absolutely none, with age difference... but possibly his inability to "perform" is due to ED if 30 something and still virgin...or anxiety if 18 - 30 and still virgin. i assume we mean virgin in all three ways ~ pussy, ass and mouth? And if the OP IS indeed topping from the bottom... go for it and tell him if he masturbates 3 days before your next "session!", he'll get a lickin [:@] Good amount of time for those balls to fill up and need less than 3 hours to pop off [:D]

Level -> RE: Virgin Dilemma Update (5/14/2006 2:49:59 AM)
quote: ORIGINAL: shygirldesires OK maybe i am plain out of the loop.... but when i read the OP's post, i thought i was reading about a Mistress and her subby boy and wondered how old they each were.... so i went to the OP's profile expecting to see Mistress aka Domme or Switch and found well adjusted, happily masochistic submissive who enjoys pain, pleasure. Now granted i am not in the loop about masochists and their needs wants desires but as i read the OP's post, i scratch my head....was that a subby boy? or Dom? As the OP seems to be the one in control or is this what masochistic subs do? Top fromthe bottom or am i just reading REALLY wrong?? Then again, if the OP is 38...how old is the male ? i have NO issue, absolutely none, with age difference... but possibly his inability to "perform" is due to ED if 30 something and still virgin...or anxiety if 18 - 30 and still virgin. i assume we mean virgin in all three ways ~ pussy, ass and mouth? And if the OP IS indeed topping from the bottom... go for it and tell him if he masturbates 3 days before your next "session!", he'll get a lickin [:@] Good amount of time for those balls to fill up and need less than 3 hours to pop off [:D] shygirl, it's nothing to do with topping from the bottom, it's merely a case of a good woman helping a virginal lad out. http://www.collarchat.com/Virgin_Dilemma/m_355251/tm.htm

merrymasochist -> RE: Virgin Dilemma Update (5/14/2006 8:52:56 AM)
G'morning everyone, TallDarkAndWitty - Yeah it does seem like I'm looking the proverbial gift horse in the mouth, doesn't it? [;)] Trust me, I'm -not- complaining. It's just that I'd like him to have the full ride too. I tried asking him what felt good to him but he seemed at a loss so I let it go and just roamed with the hopes of getting it right. Your suggestion about having him masturbate for me is a good one. That way I can see where he likes his rubbing best first-hand (so to speak)and shift accordingly. theRose4U - He may have been "busy" beforehand, I don't know, it wasn't something I thought to ask, but it's a valid question and might explain things. I'm not sure how to get him to add his own mental side in yet, though. Right now he's just seeming to want to try out everything he's ever seen in the videos. (Thank heavens I've got angleworms in my ancestry!) Mayhaps I should ask what his all-time favorite video is, rent it and see what's in it to gain some insight. MstrTiger - He's not kinky or into kink or at least I don't think he is. He's not mentioned anything in that direction yet. I want him to be happy a not feel pressured. That's why I'm here asking my questions here because when I ask him, he blushes and either doesn't know or doesn't have the words to answer. I figure if I can gain some insight here it will help me to make things easier and better for him. Level - ~laughing~ Some girls have all the luck I guess! Nope, not at all. How do you politely tell a man not to masturbate? While this is a strictly vanilla thing, I still am what I am and the idea of telling a gent something like that is about as foreign to me as shoes are to a snake. Elizabeth7777 - That's what I'm hoping, but just in case, I'm asking here. Thank you for your kind words. [:)] LuckyAlbatross - I've not a clue on how long it takes him but it's a good question to ask. I'm not worried, this was just something I wasn't expecting at all, in fact I was expecting the opposite. I'm not looking at it as a "problem" per sec, but rather as potential problem that I would like to figure out without putting any undue pressure on him. I'm hoping it is just a simple case of nerves and next time things will be easier and more relaxed for him. Kedicat - I'm glad I'm not facing a unique situation. I've never been through this with any gentleman I've known so it's had me at a loss as to what to do and what not to do. MistressLove999 - Thank you kindly. [:)] I hope so too. And btw - the condoms were trojan ultra-thins. ~wink~ shygirldesires - This is a strictly vanilla affair. He asked me to be his first and I said yes. As I've never been with a virgin (and yes he was a virgin all the way, but not quite so virginal anymore now) I want to make it right for him and give him the best introduction and the happiest memories as I can. Hence, I'm here asking my questions and gaining insights so I can do just that, rather than pressuring him with a lot of questions he just doesn't know or have the answers to yet. Thank you everyone. I've learned a lot and am worrying less about this with y'all's input and insights. Gads! Who knew virgins could be so complicated??? Take care everyone and I'll let y'all know how things progress. Sincerely, merry

Level -> RE: Virgin Dilemma Update (5/14/2006 10:00:51 AM)
quote: ORIGINAL: merrymasochist Level - ~laughing~ Somei girls have all the luck I guess! Nope, not at all. How do you politely tell a man not to masturbate? While this is a strictly vanilla thing, I still am what I am and the idea of telling a gent something like that is about as foreign to me as shoes are to a snake. Sincerely, merry [:D]......... yes, I see that it could be difficult to tell him to stop strumming the six-string........maybe tell him that men that keep their hands in their backpockets excites you?..... I tend to agree with the others, likely it was just first time jitters. Once he starts cumming, he's liable to not stop lol....hang in there, you're doing great, merry. Level

theRose4U -> RE: Virgin Dilemma Update (5/14/2006 10:59:09 AM)
quote: MstrTiger - He's not kinky or into kink or at least I don't think he is. He's not mentioned anything in that direction yet. I want him to be happy a not feel pressured. That's why I'm here asking my questions here because when I ask him, he blushes and either doesn't know or doesn't have the words to answer. The blushing honestly can mean 2 things. For me it's a huge tip off that he's sub and doesn't want to admit it. Virgins however can show these same symptoms because they haven't found their voice. As part of pillow talk you can usually get him to open up a little more and tell you what he likes. Getting them to speak openly and honestly about sex, what they like, what they don't is a lesser spoken about skill. As part of showing him what you like, how to service orally and manually teach him how to interpret the "signs" quickening of breath, moans that mean pain not pleasure, reading facial gestures and just outright I really like it when you ____. 90% of the skill is knowing what the partner likes. Too many guys think that they're great in bed because they know how to do x and one girl thought they did it well...over and over and over. Problem is when they meet a y or z he won't understand. He'll be doing x and think he was great...she'll probably be faking till she can get him gone. quote: Level - ~laughing~ Some girls have all the luck I guess! Nope, not at all. How do you politely tell a man not to masturbate? While this is a strictly vanilla thing, I still am what I am and the idea of telling a gent something like that is about as foreign to me as shoes are to a snake. Frankly this is part of teaching him to speak up. I personally prefer..."honey i'm waiting for you and can't wait, will you please save yourself totally for me this week?" He's a virgin and may not get it so telling him not to take matters into his own hands all week and save it for you may make him go hummm. Telling him what you have in mind may stoke the fires a bit too.

sophia37 -> RE: Virgin Dilemma Update (5/14/2006 3:54:47 PM)
I'll be looking for next weeks update for sure. I just hope the kid doesnt fall in love with you. I might, if I were him. LOL

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