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Ok, so I took my girlfriend's virginity last Thursday. We used a brand now box of condoms and my penis wouldn't even touch her below the waist unless I was already covered with a rubber.

We proceeded to continue the next two days with sexual activity taking note to be safe. We've used 9 different contraceptives. Further more, I never ejaculated anywhere around her vaginal region, but there was a lot of deep penetration and deep finger foreplay within her.

Now, 2 days afterward, she started her regular cycle which lasted for 4 days. Now for the last three days she's had to urinate frequently and when she did blood would come out.

What does this mean? She seems very petrified at the current moment.
Well if shes having her period it's completely normal for blood to come out... but also after losing your virginity it's normal to bleed. I'm sure everything is fine.
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So that means, even after her period is over, its still normal for her to bleed after losing her virginity correct?

So what's the cause of the frequent urination in which where small amounts of blood comes out? Is that part of it?
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Well, are you sure the blood wasn't just from her having her period? Frequent urination I don't know. She might have some sort of infection that you might need her to get checked out if it persists. As far as blood + sex goes, it's not unheard of to bleed after the first few times you have sex but if it continues then you might want to consult a doctor for that as well.
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Ok so her period ended after 4 days.. then the bleeding started two days later. Now she urinates more frequently and at first there were light spots of blood whenever she would wipe, but now on the 3rd day of light bleeding after urination... she's noticed that it's increased.

She's had no other symptoms other than very light-mild lower abdominal pain but it subsided when the bleeding started. All this is normal right? She's going to get checked out by her doctor but I'd just like to have an idea.
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Now symptoms include mid to lower abdominal pain, frequent and painful urination with blood still [going on 5 days now (two days after her period ended)], and she feels "queasy"?

Her sister informed her that she most likely has a Urinary Tract Infection? Which by the way, she's never had before.
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Yesterday, she felt "queezier" in the morning and throughout the day and the pain got up to as far up as her belly button, and the bleeding was there after urination. She also noticed throughout most of the time she would be more tired than normal.

Throughout it all, she would have frequent urges to urinate, and when she did she would seem like she is about to pee the most in her life but only a relatively small amount would come out followed by fresh and bright red blood and a painful burning sensation.

Now today, same symptoms, still blood after urinating along with the pain - its now been officially a week of this she tells me (14 days after she first lost her virginity), but she tells me the blood isn't as much as some other days, and she is now TXT-ing me that she is in the process of peeing in a cup at her doctors office. I geuss I'll know soon enough what it is...
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So.. it happens that when she pee'd in the cup at the doctor's office, she noticed that she all of the sudden bled more than any other day (probably she was nervous?)

She told the doctor everything from the very beginning and the result comes out that she definitely only has a Urinary Tract Infection - so no, she's not pregnant.

Thank God!
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Good news that its only a UTI but a good scare will go a long way to remind you both to be very careful huh?

Glad to see she's getting proper care and nothing is too serious. Her chemistry may not agree with the brand of condom or possibly the choice of spermicide (if used) or lubricant. The female body is a tricky chemical balance that can be thrown off by the simplest things.
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