From my masturbation perspective I would love to be able to masturbate with a woman while watching each other and watching porn at the same time edging ourselves encouraging each other physically and verbally. I have done it over the phone.
It would be awesome to do it in real life.
I only ever did it once with a woman at the same time outside of marriage in years.
It was a woman I used to know as a girl in high school and I remembered that she liked to have phone sex, and that she still lived in her parents house although they had passed away.
She had no siblings.
So I looked her up and made a phone call, back when you could actually look someone up on the telephone book.
And after bit of small talk I figured I'd take a chance and I asked her point-blank about some things that we used to do the summer after graduation.
In that summer and fall she used to have people over her house when her parents were out, and one time when her parents were on vacation a bunch of us were in her basement, which was a finished basement. On a dare she got naked, she started to masturbate in front of people, soon there was cock sucking, pussy licking, and lots of group masturbation. She sucked my cock and others, many times, as did the other girl.
She even encouraged another girl to masturbate together and they would play with each other's pussies while a bunch of us would watch and masturbate, even a third girl came to watch them masturbate to that as we would jerk off over them.
It only happened about six or seven times as a group over a long time, but it's the type of thing you keep in your mind for life, and this was our crazy post High School insanity. Maybe it was the new found freedom of being legal, but there was something audacious about the whole thing.
I suppose it was a certain form of rebellion, many of us had toed the line for the last year of high school, and several were honor students. Since we were all 18 there was less hesitation then you probably would have been and it was a bit of wine to lubricate the libido.
Although we had a few smaller encounters, after that everything was more or less normal and I didn't see her for at least 25 years.
Anyway, I got it in my head one day, found out that she worked at this place where she would work all alone on certain days after hours. She gave me that phone number too, and I would call her at her job she would go to her private office and we would have phone sex. This was long before security cameras.
So anyway we arranged to get together.
I had to go down to her house. She had a tape, one was playing was playing on the VCR when I came in the house. I had noticed that she was only wearing a robe and nothing else because she barely tied it, so needless to say I was excited. I could see her tits, clearly she was naked underneath.
We went into her bedroom, where she took off the robe and she was naked obviously as I said, and I could see that she had a dildo and a vibrator on the couch/ loveseat next to her she had set up an armchair opposite and a towel on it.
She told me to make myself comfortable and her casually sat back on the loveseat, with a couple of towels spread out and without hesitation spread her legs and slid the dildo right back into her juicy pussy, which she obviously had been masturbating already.
Needless to say I was hard as fucking rock!!
I got naked and when she saw my stiff cock she moaned out loud and started fucking herself faster.
The porn that was playing was an orgy from a swinger video. And it featured a scene that was playing with two women masturbating together while several men were jerking themselves and shooting their squirting cum all over them. It was obvious that she had chosen this tape to remind us of what we used to all do at her house.
I sat back, she reached over, said "catch," and threw me a bottle of lube, so I caught it and in turn spread my legs so she could see my stiff cock. I lubed it up very slowly to make it really shiny and my eyes darting back and forth between the hot pornography on the TV, and watching her stroke the dildo in and out very slow deep strokes.
While she watched me we did this for at least an hour moaning with pleasure, talking dirty to each other, and watching and reminiscing out loud. Finally, she asked me if I wanted to cum with her. I was all primed up to squirt my cum. So we went for it and we came within seconds of each other. She knew I was ready as she pointed it out to me that it it was making her fucking crazy to watch my balls tighten up, watching my hard stiff cock swell even more as I was dripping out of my cock head all over the towel. I felt a huge spasm and groaning out with lust, came hard as several ropes of hot white cum squirted out of my cock.
It was fucking hot as hell as she was fucking moaning and crying out loud, she fucked her hips back and forth legs spread wide, and squirted her juices from her wet cunt.
