I had not seen her in a couple of days.
“Did you masturbate last night?” she asked me.
“I did. I also used the toy.”
How did we reach this level of intimacy… I’ll tell you.
That time we stopped for the night on a road trip. After a nice bath and a few beers, we started to get intimate. She had started her period and wanted to limit herself. I was pretty horny.
I said, “Let me show you how I make myself cum.”
Funny how after many years of watching a girl masturbate, I had never been the ‘model’.
She was intrigued and she watched closely, alternately looking into my eyes and watching my hand stroking my dick.
Eventually, I came. She looked so satisfied. “That looked like it felt really good,” she said.
The seed was planted. Over time, it grew.
My favorite approach went like this: Her on her back, I would gently lick her clit, carefully measuring her response so that I could keep her on edge. I loved licking her and never wanted to hurry. After her first orgasm, I would have her turn over and give me access to her gorgeous butt. I loved licking her asshole even more than licking her pussy. Doing that made me very hard.
I’d reach under and barely touch her clit at the same time, but keep her on edge so I had more time doing what I loved. Eventually, she would have another crashing orgasm, and my cock was very hard. I’d slip into her pussy from behind and fuck her slowly. I’d take my time and enjoy the view of her ass while I slid in and out. She’d come again.
Many times, I had pulled out and shot my load on her lovely bottom, but this time, after she had recovered a bit, and as I had not cum yet, she asked, “Will you masturbate while I watch?”
The intimacy of sharing this with her was intoxicating for us both. I found that I wanted to share more. On several occasions, while she watched, I brought my legs up over my head and emptied my load onto my face and in my mouth. For years, I had wanted to try swallowing my semen, but it had never been easy for me to follow through after orgasm. The timing of having it immediately shoot in my mouth, and having her watch with a big smile was what got me past my inhibition. Over time, she helped train me with a wet kiss after sucking me off, or by scooping it up on her fingers and feeding it to me after I orgasmed for her. If I unloaded on her pretty bottom, she would suggest that I lick it off.
One time, at a S&M-themed love hotel room, I bought a dildo vibe and some lube from their in-room catalog. I wanted her to use it on me.
She had not done it before, and she asked how to go about it. “The kinkier, the better,” I said.
There was s horse-shaped thing in the room where she could strap me down, nude and face down. She had complete access to me. She lubed my anus, then pressed the dildo into me, sliding it in and out while I was helpless.
That toy became part of our play-time and sometimes I would leave it out on the bed. Seeing it there, she smiled. “Every time you see that toy lying there, think about how much I’m going to enjoy seeing you use it in the show you’re going to do for me later on,” she said.
My masturbation shows for her brought a level of intimacy. “I feel so close to you,” she’d say.
There was the time we were lying in bed, and she was tossing and turning, unable to sleep.
“Would it relax you to watch me masturbate?” I asked.
“Oh yes.”
I pulled back the covers and brought myself to a nice orgasm while she stared at my cock. She slept like a baby afterward.
Once, before we slept, she felt my arm moving slightly. “Are you masturbating?”
“Yes. Want to watch?”
Of course she did.
I told her once, and on more than one occasion, I followed through.
“If ever we are at odds about something, having an argument, or anything that seems to be putting a barrier between us, just ask me to masturbate, and no matter what, as long as we have the privacy, I will show you.”
Any argument usually meant that I was being the jerk, and so a jerk-off would cure me!