Hi - first, we ask that you use the proper terms. "Transexual shemale worker" is inappropriate - they are transgender women.
You're a little confused as to what is a risk and what isn't.
There are no risks from hand jobs and fingering. You don't need condoms on fingers. Hands never transmit STDs.
I'm going to give you a really long, detailed description of what you're at risk for with giving and receiving oral sex to a penis, and will cover rimming, too. I'm also going to include giving oral to a vagina, since you were in a relationship with a woman in the past. It's long, but let me know if you have any questions.
Oral sex
RECEIVING ORAL - MALE
So receiving unprotected oral sex puts you at risk for syphilis, genital herpes type 1, chlamydia, gonorrhea and NGU. You are not at risk for HIV from receiving (or giving) oral sex.
I’ll explain all the risks for everything, but most experts don't think a single act of oral sex warrants testing. If you have a regular partner you're concerned about infecting, you might want to test, but you probably don't need to test unless you get symptoms.
Syphilis:
Syphilis isn't that common, and your partner would have had to have a sore in their mouth to transmit it. You wouldn't see symptoms of this for 10-90 days, but the average is 21 days, and you'd get a sore called a chancre. This doesn't cause burning, pain, discharge, etc. You can test for this at 6 weeks. If you get symptoms, but test negative at 6 weeks, test again at 90 days, and get to the doctor as soon as you see symptoms.
Herpes Simplex Type 1:
If you don't already have herpes type 1 (think oral sores, like cold sores but not canker sores), then you could get genital herpes type 1 from receiving oral sex. This can happen even if the person performing oral doesn't have a sore, but it's more likely if they do. The time from infection to symptoms is usually 2-12 days, but the average is 4 days. You can test for this now, and then again at 4 months to make sure you don't have it. If you test positive now, it's a pre-existing infection that you had before this encounter. About half the adult population has this, and 90% don’t know it. Ask for a type specific hsv1 IgG blood test. You don't need a type 2 test, and that test has some false positives on it, so avoid it if you can.
Gonorrhea:
You'd see symptoms of gonorrhea at about 2-5 days, and this would usually be a discharge, burning, etc. Some people don't get symptoms. You can test for this as early as 3 days, but 5 days is better. You can have a urine test or a swab test.
Chlamydia:
Oral chlamydia isn't common at all, so getting chlamydia from receiving oral isn't likely, but has happened, so I mention it. The symptoms and time frame are similar to gonorrhea. A chlamydia test is usually run at the same time as gonorrhea, but make sure to ask for it.
NGU:
NGU (nongonococcal urethritis urethritis, sometimes called NSU, for non-specific) is an infection in the urethra that is caused by anything other than gonorrhea . This can be caused by normal mouth bacteria entering the urethra, and other germs, like strep, adenovirus (usually causes upper respiratory infections like bronchitis), and the like. The symptoms and testing times are the same as gonorrhea and chlamydia.
GIVING ORAL TO A VAGINA
Giving oral sex to someone with a vagina oral chlamydia, gonorrhea and syphilis. Syphilis isn't that common, and your partner would have had to have a sore that your mouth came into contact with to transmit it. You would get a sore in your mouth anywhere from 10-90 days, with 21 days being the average. You can test for this at 6 weeks.
Oral gonorrhea doesn't usually have symptoms, but if you got them, it would be a sore, red throat, maybe a fever, maybe swollen glands. If you get symptoms, they usually appear within 7-21 days. You can get a throat swab for this at about 5 days.
Oral chlamydia is thought to be rare, and usually doesn't present with symptoms. The time frame for testing is the same as gonorrhea.
Giving oral to someone with a vagina is not that risky. Because nothing is physically in your throat like a penis would be, chances of getting gonorrhea or chlamydia are far less likely.
GIVING ORAL TO A PENIS
Giving oral sex to someone with a penis puts you at risk for oral gonorrhea, chlamydia and syphilis. Syphilis isn't that common, and your partner would have had to have a sore that your mouth came into contact with to transmit it. You would get a sore in your mouth anywhere from 10-90 days, with 21 days being the average. You can test for this at 6 weeks.
Oral gonorrhea doesn't usually have symptoms, but if you got them, it would be a sore, red throat, maybe a fever, maybe swollen glands. If you get symptoms, they usually appear within 7-21 days. You can get a throat swab for this at about 5 days.
Oral chlamydia is thought to be uncommon.
There is a risk here, but oral sex is lower risk than intercourse.
Giving oral sex to someone with a vagina is is far lower risk than a penis, but the same risks apply.
RIMMING
Performing oral sex on an anus is very similar to giving oral to a penis or vagina. It puts you at risk for oral gonorrhea and syphilis, and perhaps chlamydia. There is also a possibility for Hepatitis A, though this is rare.