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!!!