Welcome to MDC!!
Are you on the pill now? Did you miss some pills or take them at drastically different times of day?
Let's break this down a bit...
CD 1 May 27th
CD 8 unprotected sex (but you're on the BCP?)
CD 9 EW CF and cramping
CD 10-20 light cramps and brown/pink spotting
CD 20-24 light period
CD 28 expected AF
CD 44 HPT-
CD 47-49 dark, clotted bleeding, light flow
This is definitely confusing if you're on the pill and taking them correctly. Occasionally you can get hormonal breakthrough bleeding on the pill, which would happen around mid-cycle and could cause an abnormal period for that cycle. Usually this happens if you need to switch pill types b/c the hormone levels are not working for your body.
If you're not on the pill now or you took them incorrectly then I would say that your body was gearing up to ovulate around CD 9 with the eggwhite CF and it could have happened a few days later. Though spotting for TEN days is not common anyway you look at it- ovulation spotting, breakthrough spotting, implantation spotting... Then you got what appeared to be AF at the end of the ten days, but it was 8 days too early.
Okay so let's say you ovulated a good 5 days after DTD (which is generally the lifespan of sperm in fertile CF) that would put O on CD 14 (as might be expected when you're regulated by the pill). That would make you 6 days past O (DPO) when you got the light period, which is possible for implantation spotting. That would make you 20 DPO when you tested, which should give you an accurate result unless the pregnancy was not viable and your hCG levels were already decreasing below the sensitivity of the test. Considering that you started bleeding just a few days later, that is possible. What we will never be able to know is if you would have gotten a positive test if you had tested earlier, confirming an early miscarriage. If you were pregnant you were about 4 weeks when you m/c.
Alternatively if we consider your light bleeding to be AF then...
CD 1 June 15th
CD 24 HPT-
CD 27 dark, clotted bleeding, light flow
This could line up with your next cycle as it is 27 days long. I am more inclined to guess that your hormones are unbalanced, causing random bleeding and cramping than I would be to guess you had an early m/c. But we can't know! What I will say is that if you want to be protected by the pill it sounds like you'll need to switch brands or be more careful with how you take them. If you'd like to get off the pill and work toward TTC then I would highly recommend reading a book called Taking Charge of Your Fertility. It's packed full of amazing information about the female body and our cycles. I learned so much when I read it and wondered why it wasn't "required" reading for every woman! It will teach you how to chart, which will allow you to know when you're fertile, when you ovulate, how long your luteal phase is, when to expect AF, if you're pregnant, and if there is anything of concern about your cycle. If you decide you'd like to try charting, you can log your data at a free site like www.fertilityfriend.com so that you can share you charts on forums like this so we can give you advice, tips, and help you decipher anything that's confusing. It's such a powerful and empowering tool whether you just want to learn more about your body, address health issues, avoid pregnancy, or achieve pregnancy.