Should losing my virginity be this painful

I know this sounds a bit... illegitimate, but hear me out. My girlfriend and I are both bisexuals. I'm pretty much the first sexual partner she's ever had, but I've had plenty of sexual experience with women, whereas I'm her first for a lot of the things we do together.

But I love her and she's really a special one for me and I want to be able to give her something. So I thought, I've had plenty of sex with women but I've never had sex with a man, so in that respect I'm still very literally a virgin! But naturally that's something she couldn't take from me... So! We decided to get a strap-on and let that count as her being my first "male penetration."

So I went out and got a dildo and, this was probably very unrealistic of me, but I got a 7-1/2in x 1-7/8in silicone one... We haven't gotten a harness yet so we've tried poking it in me a couple times just to see how it is... We tried to see how much we could get in before it hurt me, and we managed to get a little less than three inches into me (with lube) before the pain got excruciatingly sharp and we had to stop... I'm a 5'2.5" girl and I weight about 95lbs... I'm pretty tiny and the dildo just seems a little too big for me... Again I had the very unrealistic reasoning that "in a real situation, the size of my first man's dick wouldn't be up to me..." but now I'm a little worried that the dildo might ultimately just be too much for me to handle even with time...

Being a complete virgin as far as penises and dildos go... I'm really just looking for some more experienced insight. I guess my main questions would be

1.) What kind/level of pain should I feel when losing my virginity and how can I tell the difference between popping my cherry and just not being able to handle the shear size of something?
2.) Are there ways to go about losing my virginity to make it less painful?
3.) Is there hope that I might still be able to handle my gf's generous "penis"?​

Really hoping for some good news here but I guess I'm ready to be told I fucked up too if it really has to be said )';>

 

Alright, honesty time, I am a guy. But! when I lost my virginity, my girlfriend lost hers, as well, and we had a lot of discussions about it both before and after. So, if you are willing to hear me out, here're my thoughts on the subject:

1. There is no such thing as "popping your cherry". This idea comes from two facts about intercourse: A. A woman's hymen is stretched open wider and will stay stretched as long as she is sexually active. B. Minor tears in the vaginal wall are very common when I woman attempts to insert something inside herself that is larger than her body is prepared to accommodate, which leads to slight bleeding. That being said, the hymen is not broken or torn during healthy intercourse (by this I mean: intercourse between two people who are working together to create a safe and healthy experience) and is generally already stretched fairly sufficiently by the use of tampons and by masturbation to allow for a relatively easy step up to insertion of larger objects, and vaginal tearing is not a forgone conclusion. By taking it slow, and only working within the bounds of the woman's current level of arousal, pain can be avoided.

2. This brings me to the most important point: a woman's body will only (painlessly) take into it what it has prepared for. A lot of preparation goes into readying a woman for insertion. This means foreplay (however you like it) and stimulation (manual or oral) of the vulva, clitoris, and vagina. It is important that there is a sufficient amount of lubrication, yes, but it is more important, when penetration is concerned, that the vagina has expanded wide enough and long enough to except the penetrant. When I am with a woman, I do not enter her until she is at least sufficiently aroused to take one finger all of the way into her and two fingers part of the way into her. At that point, if she is psychologically ready, I will begin to enter her. It is very important to understand, however, that unless the woman is completely ready, she should not be penetrated all at once. It is a slow process, whereby the penetrant is slowly inserted and retracted, inserted and retracted, only ever as deep as woman can allow without discomfort. It can take a minute or so, but it is necessary to create the gentlest experience possible. Simultaneous stimulation of the clitoris can also be a good aid in the process.

3. Lastly, regarding your dildo, it is not an unrealistic size, per se, but it is probably unrealistic of you to expect to be able to take all of it into you having never been engaged in serious penetrative play before. I would recommend something close to 5 or 6 inches in length with a diameter closer to 1 or 1-1/4 inches.

I hope this helps. Just remember that this doesn't have to hurt!

 

I agree with you but just want to add that step #2, is hard to achieve for some ladies especially if they have psychological blocks, or fears about sex.

Those can be from a traumatic sexual experience (rape, sexual assault of some kind), to what they've been taught about sex growing up either by friends or family, which attach negative connotations to the idea, and act and therefore sensations of sex.

So while I agree that foreplay is essential, even when it is present and the guy is doing all the right things physically, the girl has to meet the guy's efforts the other 50%, and that may involve a LOT of MENTAL work on her part which often requires the girl to jettison the values she was taught/raised with.

^Not easy anybody involved.

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Also keep in mind that there are different types of hymens as well, so that will obviously affect what the OP is talking about here.

 

You've had outercourse. I wouldn't consider that virginal.

 

By the way… all this advice from men aside.


As a woman, I'll tell you its completely normal. You can be dripping wet and horny, and it can still hurt if you're not a physical match for whatever is penetrating you.

My ex husband is 8.5 inches and 6 inches in girth. OUCH! Really fucking painful and I had plenty of penetration long before him. The friction of his penis caused me dizziness, and headaches. I would almost pass out during intercourse. My doctor said it was because he was just too big for me, and he also hit my cervix way too much. We didn't stay married for long.

My fiancé is 5.5-6 inches depending on his level of arousal and his penis is 2 inches across. PLENTY. Its still a bit much at times but plenty and very satisfying. So maybe you need to try a smaller vibrator/dildo.

 

^True I didn't mean to imply I agreed with absolutes that there is no pain if the guy does ___, ___, and ___.

Sometimes you are physically incompatible, but I thought that was just obvious.

As a guy, who hears from other guys and girls, I am skeptical about my fellow guy's skills, at minimizing painful situations for their female partner.

 

Yeah, some guys are rough and tumble. They have no understanding about REAL sex, they see porn and think thats the status quo.

I get excited quickly so I can handle sex w/o a lot of foreplay as long as I'm lubricated at the start. It can be saliva, ky jelly (though that whole process of getting the bottle and squeezing it out removes the spontaneity of rough and tumble sex) - I prefer saliva.

 

That is really big for your first time. From what I have read that is significantly wider then the average penis size in the USA, 5.91" long and 1.51" diameter, according to the WIKI.

 

You would think that length isn't so much an issue with sex toys though because you can control how much you put in for comfort, but it's the girth that determines if one picked the right size toy.


Happily, care to comment seeing as you are the female commentator in this thread most active at this time.

 

Sure, to this I would say even my own finger can be frightful. And it's less than half inch in diameter, I usually only insert an inch or two. I have a vibrator, I usually don't use it though.. I only insert about 3 of those 6 inches (by 1.5 inch). Thats my comfort limit on myself. I'm totally comfortable with a penis double the size though. Maybe this tells us that women are more delicate with ourselves?

I have a feeling OP's issue is anxiety.

 

I think it is an anxiety problem as well. We only talked about other stuff because the conversation naturally progressed to encompass the topic at large.

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That said, yes I do then to think women are more delicate with themselves than men tend to be with women. I think men as they age learn to be more delicate over time....or not it just depends.


In some cultural education classes, when you get to the sexuality aspect of the class you do learn that orgasms for women and pleasure for girls and women, are more successful in certain cultures than others, even if performed by boys/men. (I am saying both girls and boys here, because lots of 3rd world countries do begin sexual activity at ages our societies would consider still kids)

This is one area where 3rd world countries are beating 1st world countries, I think less stigma about sexual topics and less false image promotions from media doesn't skew behavioral expectations in areas of intimacy.

There's no fears on the woman's part of getting negative reactions if they sleep with multiple partners, even if they started young, and same goes for guys.

Although there's a trade-off, they are 3rd world for a reason, and they definitely don't have civil rights, and might have a locked-in heirarchy of status and thus who is worth what.
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