Yes, vividly. For me and my then girlfriend it was during our first time playing doctor.
I had started to realize she was interested in having her bottom played with. We’d only been dating about a month, were having vaginal though not anal sex, but whenever I’d touch her on and between her cheeks her reaction was feigned dislike but with a grin and she never stopped my naughty explorations of that very private place (which she later told me she’d never allowed any boyfriend to see or touch, as she had thought it “perverted”).
One day I made a subtle reference to “playing doctor” and she reacted with a blushing smile and raised eyebrows but I didn’t pursue it. Now I was very intrigued and one day soon got up the courage to call her at work, called her “Ms.” pretending to be calling from a medical clinic, confirming that she’d be home this evening for her “appointment with Dr. Richard”. She paused and stuttered slightly, then to my delight started playing along and said “yes, I’ll be home ready for my exam this evening at 6pm”.
I was ecstatic and nervous and probably hard as a rock.
I began to wonder how to prepare. I kept it simple: put on a white dress shirt and dark pants, then used my black leather toiletry kit as my doctor bag. I emptied it and then put in the Vaseline and thermometer I owned (I admit to taking my own temperature before I even met her but I’d never used it on another person).
Once at her home, neither of us could stop smiling with naughty excitement. I asked her to disrobe and lie on the couch. She wanted to do the exam in her living room for some reason. After a lengthy exam of her upper body, I told her I’d need to take her temperature. Of course she opened her mouth. I told her “No” that she needs to turn over on her tummy so I can take it rectally. As I said this, very nervously, I removed the thermometer and Vaseline so she’d see them. Her eyes went wide. She said OK but said she preferred to have it done while on her back. I didn’t protest, too nervous that she was going to say “NO WAY!” to the temp taking. She later told me that she’d said this because she wanted to watch me do it to her, as it was her first time being penetrated anally like that, and wanted to see the expression on my face. This woman was definitely the most visual person I ever dated.
I knelt on the floor, my face between her legs looking directly at her lovely pussy, which I’d yet to examine. And asked her to pull her legs to her chest, which she did, keeping them open so she could see me. Her cheeks open slightly now, I placed my fingers along them and pulled them open, giving me the first real intimate view of her little pink anus. I was mesmerized. I glanced up at her and saw her staring at me, eyes wide, not even smiling, just looking so focused. I opened the Vaseline, put some on my finger, then spread her bottom open again with one hand and began to put it around and on and slightly in her tender bottom hole. After thoroughly lubricating her, I reached for the thermometer, lubed it too as she watched, then again exposed her now shiny asshole, spreading her white cheeks as wide as my fingers could. I told her to take a deep breath, and the I slowly pushed the thermometer into her anus. She was staring at me intently the whole time but never said a word. I timed it for 4 minutes. I kept “checking” it, twisting the thermometer, tugging it in and out just slightly, and repeatedly opening her bottom for no other reason than because I was so enjoying this and seeing her so intimately and looking at this adorable little rosy bumhole that I would over the next several months do so many naughty things to.
After 4 minutes, I removed the thermometer, verified that her temperature was normal, wiped down the thermometer, and replaced it in my bag. She was still silently watching me do all this, now starting to grin a little.
I then, feeling quite emboldened, told her, “Ok Ms., your temperature is normal. Now it’s time for your rectal exam.”
So, yes, I definitely remember the first time I took a significant other’s rectal temperature!