My girlfriend Jen and i moved in together 3 months ago. She knows i have a med fetish, but won't let me play around. Every time I take out the Rectal thermometer she refuses. Finally she told me when she was younger and said she was sick and wanted to stay home from school, her mom would bend her over her bed and take her temperature using the RT to make sure she wasn't lying. She told me it was slightly uncomfortable, and embarrassing She said the last time it happened was when she was 14 and had gotten over a bad cold, and nothing was been in her ass since.
About two months ago Jen came down with a pretty bad cold out of nowhere. I took care of her for the first few days, but she wouldn't take an pills to help with the cold(Jen she has a hard time swallowing pills), and she wasn't getting any better. Finally on the 3 day she asked me to go to cvs and get her vitamin C suppositories. I had to ask about the unspoken no anal rule. She said when she was 14 she had a bad cold just like this one for 4 days, then on the 5 day her mother gave her 2 Vitamin C suppositories, and the cold cleared up shorty after. I was jumping for joy all the way to cvs.
Finally when i got back i asked her what position she wanted to take them in, she just said she didn't want to be bent over. So i decided diaper position would be best. I had her sit on the couch and i pulled her panties off, i then asked her to lift and spread her legs ( I macgyvered a system for her to rest her legs on.) I put on a pair of gloves and lubed my finger. I reached out and spread the lube all over her pretty asshole. She was sick but still looked damn good to me, no reason i can't enjoy this i told myself. I took the first suppository and pressed it against her pretty hole and pressed, after a sec it started to make its way in, when jen let out the smallest moan of discomfort. I stopped my pushing with the suppository half in half out looked up at Jen's face, and asked if she wanted to stop? She told me no, keep going. That this was for the best. I pushed the suppository the rest of the way in until my finger tip was even with her asshole. I asked if it needed to be pushed in farther? She said that her mother pushed them in till her first knuckle. Jen took a deep breath and told me to proceed. So i started pushing my finger past her hole, i could feel it warped around so hard on my finger. Jen was openly showing her discomfort now, saying it hurt. I was up to my first knuckle now and was about to pull out when Jen told me to wait 10 seconds, to make sure the suppository didn't slide out with me finger. I then pulled out gently and slowly.
After i gave her the second one, I asked her how she was doing, and she told me, it hurt her to have the suppository, and then my finger in her ass, but knowing it would her her get better made it worth it. Also knowing that you like giving me the suppository makes it less embarrassing too she said. With a small smile on my face I said I'm happy to help.