I've been curious, off and on, for years, about what kind of sensations I would receive from some ass-play from someone experienced in that area. My soon-to-be ex-husband had never expressed any interest in the topic and the furthest I had gone myself was to sometimes rub my finger over my asshole when "taking care of myself" on occasion.
My opportunity to experiment a little (a lot!) more happened recently, when I realized I would need a ride home from my (ugh) colonoscopy. My doctor had recommended I get one as a baseline for future comparison, not long after I turned fifty. I'd been putting it off for a few months, then made the appointment with the idea my husband could bring me home -- then we separated.
I have this one guy friend (truly an awesome friend) I've known for over twenty years. He's always been there for me when I needed someone and, I suspect, has always wanted to be a little more than just very good friends. Hey -- I'm essentially single now -- why not offer some bait and see how far he goes?
Bob didn't take much convincing -- all I had to do was raise the question of how I would get back from the hospital after my procedure and he was only too eager to volunteer to take the afternoon off work and transport me. I didn't try too hard to deter him, to be honest.
So the day of my procedure rolled around and at that point, I couldn't wait for the whole ordeal to be over -- it's not so much the procedure itself, it's the prep (read: internal cleansing) prior to it that's awful. By the lunchtime of the day itself, I was hungry, cranky and felt I'd flushed out my internals as severely as if I'd had the equivalent of food poisoning (without the cramping). Bob showed up around noon and drove me over to the local hospital for my procedure.
We waited quite a bit, then they took me back to get undressed and then they had me lay down while they administered a mild general. In no time, I was out of it. Next thing I knew, I was woozily sitting up and being directed to get dressed. They sat me in a wheelchair and wheeled me out to the doors, where Bob had brought the car up. The wooziness left me almost instantly as the cold wind hit my face and whipped my hair around, snapping me back to alertness.
Bob helped me in the passenger side and drove me home, uneventfully. I pretended to be more out of it than I really was, hoping to encourage him to take more care of me than I really needed. When we arrived at my house, he parked in driveway and asked me for the key-code to my garage, which I mumbled to him, acting still out-of-it. He supported my arm as he led me in through the garage and into the main part of the house, walking slowly and carefully the whole way.
He sat me down on the couch while he let the over-exuberant dog out the patio door, turning back to me to assess my grogginess. Having apparently decided I might be persuaded to let him "help" me a little more (was my plan working?), Bob suggested I lay down while he got a warm washcloth to clean me up a little. No objection from me! I lay down on the couch on my side, facing outward toward the main part of the room while Bob made his way upstairs and into my bathroom (I could tell by the creaking) to procure a washcloth. He brought one back down and as he ran the kitchen water to get it warm, called over to me "can you lay on your belly, please?".
I pretended not to hear properly, so when he came around the couch with the washcloth, I was still laying on my side, acting groggy. He placed a couple pillows in front of my groin, then pulled me over, toward him, so I was on my tummy with the pillows pushing my butt upward. He then proceeded to tug my sweats down to around my knees, finding it far more difficult than he probably expected, as I was not offering any help whatsoever!
Next, there was a bit of a pause, where I assumed he was feasting his eyes upon my upturned, panty-clad butt. I shifted from side to side a little, rolling my hips, which seemed to have the desired effect of stimulating lecherous Bob out of his butt-trance.
I felt his fingers in the waistband of my Vanity Fair's, starting to shimmy them down over my hips. I made this a bit easier for him by pushing my knees into the couch and raising my pelvis enough for easier access. The underwear joined my sweats, pooled at my knees. I could now feel my exposure to the room at large. Goosebumps formed on my normally-covered private flesh.
Bob's hands, hesitant at first, palming my butt-cheeks, just resting gently on them, not pressing too firmly. His hands were a little cooler than my own flesh, stimulating the goosebumps even more. I felt his thumbs extend toward my crack, push down a little, then pull my inner cheeks apart enough to expose my rear hole to his prying eyes.