Is sex sore? Really shouldn't be, unless the sizes of your respective vaginas (entrance or length, but consider also vaginismus which 90% of sufferers don't know or even suspect they have)... Five fingers thick? That sounds to me like unnaturally large and I would, had I a vagona of a size I have seen before, expect that to be very sore, virgin or not, and quite possibly enough to tear tissue unless you have the deepest, widest and most elastic vagina I have EVER come across!!
The FIRST M/F sexual experience is, obviously, the time pain is most likely. I recall the Love of my Life (a woman, 21, virgin) whose first time was interrupted several times (and my penis is almost average size/girth according to the textbooks - girth unknown, length when erect 14.8cm...) by fear of the sheer amount of blood from the vaginal entrance - tearing of the hymen - and the associated pain, which in her seemed very intense, and which event lost its penetrative nature, ending with an orgasm gained through my tongue (which she found at first frightening but as I gently stimulated her hood and especially frenum & surrounding bit of the glans - which was very large and therefore easier for me to relate to my penis - she calmed down almost like she'd taken a Xanax, and this relaxation led to her first orgasm. Before this (she was a very devout Episcopal Anglo-Catholic with heavier "guilt" even than the Romans!) and despite going through puberty VERY early - just after her 8th birthday - had never masturbated; she had felt her erect clit through her panties/pyjamas a luple of times but as soon as that pre-orgasmic pleasure started, she would freak and stop touching herself immediately.
That's a background I hope you relate to.. I am not only bisexual, having had my first serious sexual relationships at around 13 at the all-boys' boarding school I attended (I still get very excited at the memory of one of the beautiful boys 2 yrs below me who had the second-best sexual touch I ever had; the best was only 4 months back, and she was - according to her and everyone who knew her in this town - lesbian, full stop!
That relationship proved to me without doubt that gays and lesbians are definitely a lot better at sex than straights. Not one of my straight relationships ever gave me the feelings as she did, or indeed my schoolfriend. He may have been an extremely sexually precocious 12 year old (he has now been married 30 odd years & has four gorgeous kids between 10 and 24... Shannon on the other hand remains lesbian and sometimes gets in touch (at dreadfully unfortunate times) to ask if she can stay over (OMG as if I'd refuse - she has the most lovely tiny titties and (when she hasn't used a razor) adorable sparse "peach fuzz" - she has now turned 18...
Here's the rub.
I have always thought I was born with the WRONG genitals. I feel, and have done since I was (as I recall) about 5 or 6, that I was a Girl and at so many junctures in my life, that's been very painful. I think identifying as bisexual - more recently after reading an interview with Christine (the Queens - Heloise) PANsexual. However, Shybigirl, embarrassment is NOTHING compared to the HELL you go through when most of the potential partners you may love to have more than a nice wee chat with are not available for you and your sexuality, and, what's more, could even affect your life, your reputation etc in your local area - living in a relatively small (60,000) place now after the amazing, tolerant and lovely city of Edinburgh, and as a practicing Anglo-Catholic (Episcopalian) there are perhaps more LGBT-friendly Churches than anywhere else I have found. May I mention two Parishes in particular? The wonderful St Michael and All Saints, & Old St Paul's - both extremely historic and ver traditional, almost like pre Vatican II RC Parishes which - if they survived - now operate in shadowy realms outwith Vatican control but retaining their Tridentine traditions and closer links to the Catholic Wing of the Church of England and Scottish Episcopal Church. I assume from several clues that you're American, the ECUSA is (despite its early moves towards female Deacons, Priests and Bishops) in fact less Liberal theologically on the whole.
I note your opinion on "rough" sex. I agree. I am not a fan, I am into very gentle stimulation and approaching orgasm by increases in speed and (without getting rough in the least!) pressure - as I (who has, unfortunately, a penis) do myself when masturbating using my lubricated fingers circularly on my frenum and the bottom of my glans, switching for a couple of secs to the shaft - in other words, my m. Asturbatjon is almost totally analogous to a girl's, which ma. aybe explains why my current favourite partners are very young lesbians whom I can convince to have sex with an unreconstructed "male" whose sexuality is cloudy but who believes he should be female and, what's more, a bisexual in the wrong body with an 80 % leaning, despite physiology, towards Lesbianism. So far I have met (all online, 2 from USA, 2 from Sweden and one from Cambodia) a total of only SEVEN people who share all my leanings. Am I really that rare? I see it may have been right to be circumspect with my sexuality. Only 2 people, both lesbians and both of whom I have slept with, know my story. I mean, of those I know in person, here.
You are 22. Yes, it is old in terms of sexual maturity but I have known but one female of 13 who was both sexually AND psychologically mature enough to have adult relationships. In this country. We have the 2nd highest age of Consent in Europe - 16, only Ireland is higher - but it is widely ignored. And a lot of folks (for appearance's sake?) get all hot and bothered about "paedophilia" without even understanding the concept! It means somebody who (male or female) are sexually attracted to children who are BELOW the age of puberty, which in anybody's book isn't right at all. You are not physically ready to have sex in general till your body gets to Tanner Stage 3. (Roughly over 13 or 14, as most laws state.)
Recently, thanks to being seduced and given the best sex of my life by these three, could be described as hebephiliac or, more accurately, Ephebophiliac - that is, sexually Mature folk between, say, 14 and 20, which is generally perfectly legal and, certainly in females, at the peak of their sexual prowess. Boys reach that state a couple of years later. Say, 16 minimum but still clumsy and largely uneducated about female responses until 20 at least!
Finally I get to the question - are you FAILING this guy zexually?
Now if you haven't discussed it together, there's a problem. Instead you come onto the forum. Oh yeah, smart - you will get others' stories (like mine) & a lotta decent advice, but I learned years back that there is no substitute for F2F talks when it comes to your sex life with someone (gender irrelevant unless you feel you have made a wrong gender choice) whom you THINK you are in love with. And that's a very hard thing to be certain of, trust me.. You ask if masturbation (mutual? Or is he selfish?) and Oral Sex is "enough".
I find both to be beautiful, as long as you educate your partner CONSTANTLY until it's 2nd nature, as to exactly what "does it" for you. And vice versa. Penetrative sex is entirely different in terms of pleasure - I prefer, with a female, that she goes on top - that's the only way you can ensure that you get your clitoris (make sure it isn't dry!) to align exactly with the male public bone (it's known as TRIBBING) and YOU do most of the moving, ensuring constant clitoral contact, and therefore controlling your own sexual stimulation. Trust me, guys (well, me!) love being f*cked from above with your rhythm (male and female orgasm come at the same wave-rate of time, forgotten the precise gap between orgasmic waves...) and of course it's best for YOU too!
Look, as a very screwed up person with serious gender issues but a very good understanding of sexual practicalities and psychology, I hope you find something in here to help you. You may even, if you reply, be able to help me, and maybe even fill me in on the odd random question.
I will keep hold of your screen name in case I need you!
Best of luck. Best pleasure WITHOUT any worries or paranoia. Let us just enjoy our best eroticism! ♥️