Of course. But it’s somewhat challenging to achieve an orgasm without any emotionality. And the idea of Data masturbating raises a plethora of questions.
So you HAVE met my ex-wife!
He has no feelings and he never gets bored. What reason could he have for jerking off? 
Because it’s something humans do, and he wants the full human experience.
Of course, the whole “wants to be a real live boy” thing proves Data, even without his emo-chip, is not a completely emotionless creature. Desire and discontent are emotions.
I can see him going to Geordi and asking his advice on which lubricant to use. Ew! :eek:
Depending on what the lube is for, Geordi is either the first or last person to ask.
AstroGlide, of course
I wonder if the replicators can handle those high-end Japanese posable dolls…
Wasn’t Kirk annoyed in an early episode when it turned out he’d been given a female yeomen?
“The Corbomite Maneuver.”
I just want to show my appreciation for this post.
Never heard . . .
[searches the Urban Dictionary]
[searches the Kama Sutra]
Data got an emo-chip? I don’t remember him being in Spider-man 3.
And he has encyclopedic knowledge of all subjects, including how to find a clitoris, so the answer to the thread question is presumably “Very well indeed”. 
No, you’re thinking of Data’s brother Sybian.
Or his sister, Allotta Fagina
His favorite p-funk 1970s era song is Flesh Light
Answering the OP’s question, this is an excerpt from the TNG episode “Deja Q” (S03E13):
[IN TEN FORWARD]
Q: I’ve never eaten before. What do I ask for?
**DATA: **The choice of meal is determined by individual taste.
Q: What do you like?
DATA Although I do not require sustenance, I occasionally ingest semi-organic nutrient suspension in a silicon-based liquid medium.
**Q: **Is it good?
**DATA: *It would be more accurate to say it is good for me, as it lubricates my bio-functions.
*Can we infer from this that Data sometimes needs a laxative? :dubious:
Data, at one point, said he could not speak with contractions, but had already done so in previous episodes and would henceforth still, occasionally, do so. It was a stupid limitation, anyways.
Woosh
Explanation: contracting one’s abdominal muscles in order to facilitate a bowel movement. Yeah, it’s lame and a stretch, but so is our endless nitpicking about anything Trek. 
Signed, Proud Nit Pickers Guild member since Phil Farrand’s first book
.