Today, as I was re-reading one of my old Cosmo issues, I stumbled upon a “first time” blooper in which a girl is making out with her boyfriend of a few months whom she hadn’t yet had sex with when she decides she’s ready to go all the way. Lustily, she tells him that she’s ready. While that may have been music to many a man’s ear who had been waiting patiently for months for their girlfriend to be ready to get down and dirty, this man was not only unimpressed with her exclamation of readiness, he was downright crestfallen. Why? Maybe you can tell from his response to her, which was “I”m already in you. I have been for a while”. Oops!
This story is far from the first in Cosmo blooper history to recount such an experience. In fact, not only have I read this story several times to varying degrees in Cosmo, I’ve also heard the story from several of my friends over the years. And not just from women, either. I have guy friends tell me of encounters they get into where the woman they are with is so loose they often only know they are inside of her because of the general feeling of warmth and wetness. I even had one friend tell me of one time where he was lying in between of his date’s legs kissing her, and when he reached for himself to stick it in, he discovered that he already was! And, I would like to clarify that we are NOT talking about men who are under-endowed. One of these “loosey-laura” stories was actually from a man whose manhood makes some women’s knees clamp shut in fear automatically (you know, guys who give literal meaning to “hung like a horse”).
When we were in high school, one of my best friends lost her virginity to a guy I had been lusting over since day one of my grade 9 year (in retrospect, he kind of looks like a bird, so I have no idea what I was thinking – but maybe the following story has coloured my perception of his attractiveness). The following day, when she had told the crew that they had finally “did it”, we were all bubbling over with excitement for her, but she seemed less than enthused, exclaiming how amazing and wonderful it had been. In private, she had actually curled up in a ball laughing while telling me “Oh, my GOD Ruby, it was like as big as my pinkie! *inane laughter with random words here and there* Now I know why he never wanted me to give him a hand job or blow him! I didn’t even know he had it in! The only reason I had ANY idea was because he said ‘oh baby, it feels so good inside you. You feel so amazing!’ I had to fake it the WHOLE TIME!! What a waste of a virginity!”. Ok, so what can I say? Teenage girls can be bitches, but at least she had enough decency not to tell the whole world about it. And in all fairness, after billions of kegel exercises and some create Cosmo-Sutra positions she managed to get at least some vague pleasure from her encounters with him.
I’ve heard so many stories over the years that I began to become terrified after breaking up with a very well endowed boyfriend that either A) I would now be loose and the next guy would have to ask me “is it in yet?” every time we hooked up so he could put on a show for me to spare my feelings, or B) That, if the next guy was slightly below average, since I was so used to being more than overfilled that I would have an “Ummm, Ruby, doesn’t it feel good for you too?””Umm, doesn’t WHAT feel good?” kinda moment with him. Luckily, I have yet to have that issue, although in all fairness I have been in a couple relationships with men whom I discovered were, umm, lets just say “petite”. Let’s also just say that some of those men may have gotten through to home base if I hadn’t been so completely terrified of having one of those moments and reacting wrong and destroying a man’s ego, and in the process useless raising my “count” of sexual partners. I mean, seriously, who wants to have to tell their partner “I know baby, I have actually slept with X amount of guys, but TECHNICALLY since I didn’t feel 4 of them, I don’t think they should count, so really my number is Y”. Definitely wouldn’t fly with me if my man told me that.
But, that situation raises a major question. Well, two actually. The first is, what is the best way of handling a sexual encounter where you just aren’t feeling it — literally (especially if you still really like the person and this isn’t a quickie hook up). And secondly, is there any way of you knowing that your partner can’t feel you (because in these types of situation it seems like the person who is pinkie-small or black-hole big can feel it just fine and is getting their rocks off like there just ain’t no problem). Honestly, I don’t have a sure-fire answer on either (hell, I don’t even have a may-spark-on-occasion answer), but here are my thoughts on the two. But, please, if you have ANY suggestions or have any experience in the subject please share with the group.
1) OK, first off I have to let you know, I am the ultimate honesty freak. I tell the truth, about everything. People tell me I am brutally honest, unnecessarily so. I try to be polite about it, but I give what I hope to receive in life, and being 100% informed, being 100% aware is what I want, so sorry guys but it’s what you’re gonna get. But while I believe in being 100% honest about everything, this is a tricky one. Because this is about the only situation in which I think being brutally honest would be downright cruel, entirely counterproductive and just plain ol’ mean. But, at the same time, faking it, avoiding it, or downright lying about it is immature and will end up meaning you spend a lot of wasted time on fake-gasms. Plus, you’re totally going to be misleading your partner and may even cause harm to your relationship as at best the sense of openness and intimacy will begin to erode. At worst, you’ll begin to resent your partner for not pleasing you even though they’re none the wiser, perhaps letting the revelation explode at them in the worst possible way: in anger, spitting it out to try and hurt the other person.
Ok, so all of that being said, I think if your partner asks you if you think they are ‘too small’ or ‘too loose’ be positive without lying. A woman can tell her man “well, to be honesty, I have been with men who were a bit thicker/longer”, and a man can tell his girl “I can definitely tell that you’re comfortable with me because I feel that your muscles are relaxed and open to me”. This will address the issue and you can admit to having noticed something I am sure they are aware of without making it seem like an issue. Because if you outrightly lie “What? Are you kidding? You’re the biggest guy I have EVER seen! Are your parents half horse?””What? You mean you’re not a virgin? You were SO tight it was hugging my manhood like it was about to go off to war!” they’re not stupid and they’re going to pick up on your BS and think that the problem is even worse than they feared.
Now for the positive part. Again, if you say something like “well baby, as long as you keep being as great at oral, then I’ll always be 100% satisfied 😉 ” you’re going to scar them for life, making them avoid sex with you, and probably even general intimacy, like the plague. Of course, praising their oral prowess isn’t a bad thing, as long as you pair it with something that you honestly like about having actual intercourse with them. And if the only thing you can think of IS the oral, then maybe you need to do some research into “tightening” positions and then make some suggestions. Saying something like “being with you is so exciting, and I’m so comfortable with you that I can be totally open about exploring sexual things with you. I would love if one day we could try_________. Is there anything you’ve been craving to do?”. Involving them in the conversation makes it seem like less of a directive and more of an opportunity to be more adventurous with each other in the bedroom.
Now, as for 2, I have no idea. I mean, realistically, unless your partner is a prick, or is one of those brutally honest no matter what people, nobody is going to tell you upfront that your size or space is highly inadequate to them. You can always look for little signs, like if your man regularly seems to soften while having sex with you (and isn’t drunk) and you end up “finishing him off” in some other way, or if your girl’s moans seem to not necessarily be in rhythm to what you’re doing, or if her body seems calm and relaxed (sexual excitement causes involuntary tension, at least to some extent – you can also try and gauge perspiration, flushing of the face and neck, and wetness, although because those things vary from woman to woman it would be hard to tell what’s just part of her natural chemistry and what’s because of, well, your natural physical make-up), but that being said chronic fakers are pretty good at, well, faking. Best bet, if you are really worried, ask. Try and gauge their reaction for indications of deceit or discomfort. And if you think it might be a problem, do your research! Find out positions or things you can do to maximize (or minimize) your love.
What do you guys think about all of this? Are you just as lost as I am and just dabbling at the answers, or have you been in the experience before and have a hilarious story or some good advice to share?
I have officially completed my first post on Sex!! Classic Ruby: Unadulterated is on it’s way! Let me know what you guys thought of it.
Cheers
Classic Ruby: Unadulterated 
Congrats Ruby! This was an excellent approach to the topic, and I was hanging off every word! It’s funny, but I haven’t been in that position before because of my man’s size, although once I was in that position because I was so intoxicated that it numbed my neather regions!! I felt so bad because he really had his heart into it, so I just moaned it out and moved like I always did, hoping that would get him off.
NOPE NO LUCK!!!I ended up having to fake-gasm (I love the term by the way) and all I could think was thank God I had did all those kegel’s otherwise he would have noticed for sure. And if it ever happened I would do it again. No questions asked. I’m sorry Ruby, I totally get your logic, but point blank I am a chicken. A big yellow belly. I just don’t have the guts to, even in a nice way, say something like that to someone!!
But…if a new guy came into my life and he was that small that it wouldn’t be worth it without some effort………point blank, I would be outtie baby!! Shallow yes, but I couldn’t spend the rest of my life with someone who couldn’t easily please me, so why waste the rest of the year with them either?
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@ Lina Lee
LOL, what a situation. I guess it brings a whole other meaning to the phrase “Be Prepared”!
See, its funny, I was just reading another blog, (the imperfect enjoyment – check it out its in my blog roll) and I posted my comment on the concept of fear. Because you would be too afraid to just deal with the situation head on, you tuck your tail between your legs and run. But as a result you might be giving up on the love of your life simply because he isn’t well endowed. I totally understand your rationale it’s just…it doesn’t make sense to me, because I would much rather get unconditional love, respect, understanding, openness, devotional and eternal bliss with an amazing sex life with a man who is attentive and understanding, even if that means that at first getting into that perfect vibe might take a wee bit of work.
I mean, obviously there was some chemistry and the dude can probably do everything else like a champ otherwise he probably wouldn’t have gotten that far with you, so it’s not an issue of chemistry. IMO it would be worth at least a conversation…
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I agree with Lina’s last point, if I ever got with a dude and his below the belt region was teeny-weenie, I would politely end the night, and then he would never hear from me again.
I once asked a guy I had been seeing for a while how my tightness factor measured up to other girls. I didn’t ask him directly, I said “Do you think I should start doing kegel exercises? Those are the ones that strengthen you Pu$$y muscles so I’ll feel tighter. Of course, if I am already too tight, it might be uncomfortable”, he was so impressed I wanted to try something new to impress him and make it better for him, he learned some new tongue moves (LAWD)as a reward.
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@ Anonymous
I like that tactic, kinda sneaky as you do have an actual agenda, but still something that can 100% also be just an interesting conversation and a way of further improving your sex life! So… I’m guessing to find out whether you were “loose” in his books you were waiting to see if he gave you a yes, do the kegels (yes, you’re loose) or a no, lets not risk it (you’re probably pretty tight) or some answer in the middle that will give you some idea which end of the spectrum you fall closest on…I guess my question is, WHAT WAS HIS ANSWER ?? 😉
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For a sex post is was definitely tame, and not something I would get in trouble reading at work or school (still not quite pg 13) which I appreciate since anything too vulgar rubs me the wrong way.
I have an embarrassing OOPS story. After a couple drinks my man and i decided we were going to get it on while at the club on the dance floor. Ok, he’s not the biggest and I’m not the loosest but I have “experience” and he’s “underaverage” but we make it work with lots of interesting positions.
We start grinding with my back to him and he reaches up the front of my skirt and starts playing with me. After a while he kinda bends me over at the waist a little. He keeps playing with me and I waited at least 4 songs for him to enter me but he never did so I finally cum and just keep dancing since he won’t let go of my hips. I was gonna face him and kiss him and ask him why he chickened out on the intercourse, but as I started turning I realized he WAS in me! I hadn’t felt it at all until I almost ripped him out of me!
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@ Dlite
Are you serious? That would have been hella embarassing if he had caught exactly what was in your mind! Luckily you guys were out in public (which is SUPER ballsy of you, so way to go on that note) and covering up your misdeed by dancing so he was probably none the wiser.
And yes, while you will see a huge variety of material on this blog, one thing you will not see from me is vulgarity. Openly vulgar things make me cringe, I like to take a more low key, to the point without being unnecessary-with-it kinda approach.
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ps the small penis picture had me absolutely rolling!…because sadly, it is VERY true, as your story clearly shows
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she so loose my dick can’t tell its in her, she’s been bangin watermelons on the real and i love me a freak! I wouldn’t marry her, but she could have my kids, she got enough room she can push em out no drugs, it’ll be a cheaper hospital bill
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@ Kinetic
Wow, Kinetic, I always wonder what bright and colourful commentary you’re going to provide us with! But watermelons and hospitals….LMAO not at ALL what I was expecting. So you wouldn’t marry her simply because she’s a bit loose and may have a “past”? I’ll ask you the same thing I asked the girls…if you found a woman who was absolutely everything you were looking for and that was her only non-redeeming quality, you would rather give her up then try and work with her on it? I would think there are MANY super whores out there with really good genetics who are as tight as virgins but have slept with 200 guys (or worse, haven’t slept with too many guys but have blows all of Ontario…just saying
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I recently came accross your blog and have been reading along. I thought I would leave my first comment. I don’t know what to say except that I have enjoyed reading. Nice blog. I will keep visiting this blog very often.
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As for the post, I found it rather comforting that someone has thought about this too. Like yourself, I too have been called “brutally” honest. Here’s the thing though, when I’m not being brutal about an opinion, people shrug it off.
Ok, my answer for the first question.
Personally, I find that “love” and “sex” go together. I’ve never had a hook up or a one night stand (not saying that they are wrong, it’s just how I live my life). So if I was really serious about someone and was disappointed in their gifts, I would find someway to work around it. Telling it to their face would be out of the question, but gesturing different positions? Yes.
And the second question.
It’s all in the emotion and facial expressions. Most guys, probably like “Kinetic”, will definitely change their emotions toward you if they can’t feel you. Girls seem to be either one extreme or other…they leave and give no number -or- they find new ways to enjoy their partner.
Great post!
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@ Tiffany
Oh, thank God, I thought I was the only brutally honest person left on this planet…well, I guess while we’re not extinct we’re definitely an endangered breed ! :-p You probably get brushed off because it’s not you to be the wishy-washy type and people are very good at picking up on someone who is expressing their opinion without true conviction. I know thats what used to happen to me, so now I vow to 100% be me…no matter how many evil glares I rack up in a day.
I hear you on the hook up/one night stand situation, as like you I tend to not live my life that way. I prefer to sleep with someone once I’m committed to them (and vice versa) and I am a serial monogamist in the worst way.
I agree with you that when it comes to gauging a random guy its probably just that easy – men are pretty much open books in most ways. However, I think a man who loves you or is totally crazy about you might intentionally hide those innate instincts because they don’t want to hurt you and push you away
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Not everyone will be a “perfect fit”, the shoes need to match the suit, and you can’t alter a pair of shoes. If the shoe fits … don’t return them, but keep the receipt just in case.
We always sacrifice something in a relationship, but most people are unwilling to sacrifice sexual pleasure. Good sex can be an unusually strong bond, and can be the foundation of a relationship that can hold it together when all else fails, when under other circumstances the relationship may fail without that sexual bond. And, bad sex can be a deal-breaker, because very few people are willing to sacrifice sexual pleasure.
– Thom
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@ Mr_Butterpants
So very true. In fact, sex and sexual pleasure in a relationship are SO important nowadays it makes me wonder how in the world people used to figure out they were compatible, and what they would do once they got married and deflowered and then suddenly realized that they had 0 chemistry between the sheets? Is this where the concept of mutual, acceptable affairs comes from?
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Great Post Ruby!
To be honest, I had to fake it with a few girls myself. Not only they were loose, they were terrible in bed.
I often hear women complain about men sizes but not the other way around. Some men actually make fun of women for being super loose and NO they’re not small. This goes both ways.
However, since men cannot complain about women loose vaginas because they get ridiculed by other men for being small, they tend to shut up about it.
It isn’t fair but that’s life.
I really hope majority of women don’t choose men just for their penis size.
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Wow，great content and your blog design is just gorgeous. Is this template free or not. If so, would you please share this template? if not, Where can i purchase it? Thanks a bunch!
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@Coach Handbags
Thank you very much. It’s a free template from my hosting site, blog.com. I believe it might be a wordpress template, also free if you register or download, or whatever it is you do with wordpress. Try them, and good luck!
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@Lacoste shoes
I appreciate that very much! I’m glad you were able to learn something, however frivolous! lol And I’ll do my very best to keep it coming, each Monday, Wednesday and Friday, as well as our new edition of Slam Saturdays! Don’t be a stranger now!
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Maybe you could make changes to the webpage subject title Is It In Yet??? (“Down-There” Size And Space Issues) Classic Ruby: Unadulterated to something more suited for your blog post you write. I liked the the writing even sononetheless.
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I’m not sure how I got to this article, but a few things: While my current partner doesn’t have a size issue (All-American Average 6, or what I think of as a solid “medium” or “just right” in circumference, texture and density), I have been with men with micro-penises (about an inch fully erect), or three inches, with 1 inch of fat mushroom head, or slightly bigger and fat, but mostly soft, etc, to seven-inchers who were thin, and fat, respectively.
I like smaller penises better. I’ve done kegels since fourteen or so (An avid Cosmo reader myself, even then. 😉 ) and with age have learned that “hard sex” isn’t necessarily good sex. Any number of women find it difficult to orgasm with only direct vaginal stimulation, and getting the cervixed bruised or bloodied (been there!) is never fun.
Also, men with smaller penises have absolutely no lesser amount of attention: the stereotype they can eat out better tends to hold, and they use their hands, they *touch*. If a guy can’t make you come just using his hands, he probably can’t make you come using a seven inch cock either.
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I don’t disagree with anything you’ve said. And personally, I don’t come from penetration as a general whole…however, in my admittedly limited sexual experience in comparison to some, where I am not over 10 sexual partners, I have found that if you are below a certain size I just won’t really enjoy it…it doesn’t do much to stimulate or whatever, so it feels more like a finger in there, which to me has never been an enjoyable feeling, no matter who is doing it. Not that I would let anything mammoth in there lol…I have seen up close and personal some…basically half ,man half horses…and I took one look and just said no…not in any whole, ever in my life. Never lol.
I think in general though I may be slightly off the norm when it comes to all things sexual in general…so perhaps many other women out there have had a couple micropenises and one of them was the best sex of their lives…or perhaps the emotional attachment you had with said men played a part? All I know is, good on you for keeping up them kegels…we should start a Cosmo Kegels: The right way club lol.
I’m telling you, if you ever get a back injury and need physio, their gonna love you when they need to teach you some of those exercises!! 😉
Thanks for your comment!
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