1-20-19 5:30 am ~day 21 of the journey sr5
With a nod to @neveryman.
Last night I slept with Helix. I knew when I went to bed that this was the plan so I just used Vaseline, which I could do without giving away my activities. I am over the moon with the feeling of Syn going in. All day long my “man pussy” had been aching. I had even taken some time to pleasure myself down there during the day. Pulled at my cheeks and then at my hole. Felt great and also relieved the sweet aching for a while. Also, as I lay in bed someone on chat said something about loving to have anything up his ass. So when Helix went in it felt so right. I moved her around in my rectum for a while – also good, but soon I rolled on my side and went to sleep.
When I woke at about five I knew I should get Helix out and return her to her hiding place. I tugged at her a few times with my sphincter, but she wasn’t moving smoothly (dididididididi), so she was coming out. She asked to be pulled out slowly so I obliged, every curve having its own sweet journey through the canal. Uuuuuuuu. It was time for a finger “warm down.” Ring finger from around back. I used the pad of my finger to push slowly on the opening, and my anus welcomed me right in. Wet… Surprisingly wet. Sweet massage and exploration in my canal. Then it was middle finger’s turn; he’s the expert. More wetness, more exploration. Remaining fingers massaging my cheeks. Pulsing… It was my prostate throbbing from the pleasure of my fingers and an occasional nipple pull. So intoxicating to feel that gland at close range! I began pulling up hard against my outer sphincter. Rrrrrrrrr!!!
All the wetness made me think that Helix would be a welcome guest. Sure enough, she slid right in – all the way in for a moment, and there was enough of my own lube for her to slide nicely with an anal tug. But then it was time for her to play in the vestibule. Her smooth body made it possible for her to give a firm massage all around without causing the least bit of discomfort. This was exquisite. All her different curves revolving around in my canal, assuredly and firmly.
She also had inspired a nice glob of precum to flow from my meatus. I was mostly soft with just a hint of tumescence. As I used my natural lube to press, and verrrry slowly rub my head, sulcus and frenulum, I was getting the most wonderful sensations from massaging the internal anatomy of my penis. I was pressing in and slowly down my shaft without my finger losing its hold on the spot where I had placed it. Then something unexpected happened. My shaft skin began folding in over my finger as I reached further toward my scrotum. Such an exotic revelation. I was getting to know my cock in an entirely new way after more than 40 years of sexual exploration.
By this time I was in my own heaven. I was back in my anus with my middle finger again. I couldn’t (can’t) get enough. The sensations are perfect – alive, but not too sensitive – exquisite and not begging to be rubbed or ramped up. Eventually I did start to become a little less wet, so I withdrew, but I lingered at the mouth and savored equally beautiful sensations there as I pushed slightly in and back out with the pad of my finger. This is an experience I will be returning to, maybe tonight. h…h…h…h…h…..
Source: https://www.aneros.com/blogs/give-me-the-finger/