How did you get into fisting?

(Submitted by Cougar in Training)

Jack’s Answer

I’m fairly certain that the first time I fisted someone was around age twenty-one or twenty-two.  The woman was a casual fuckbuddy who sustained me through a couple otherwise dry spells during my twenties.  During a long and very exciting session of foreplay one evening we found ourselves naked and making out on her bed.  She was playing with my nipples while I fingered her pussy.  I’d slipped two fingers in, but she wanted more.  Soon I had four fingers inside her, my thumb rotating slowly on her clit.  Then she asked me, somewhat awkwardly as I recall, to give her my thumb, too.  I was aware of fisting, though I’m pretty sure I regarded it as the stuff of urban legend; still, I did as I was asked.

I didn’t get my hand all the way inside her, i.e. all the way to my wrist, but for all intents and purposes my entire fist made it in.  Having already found her G-spot I resumed stimulating it.  She climaxed almost immediately, her intense moans during the buildup the perfect encouragement for me.  When she drenched my hand and my arm I was fascinated.  I’d found a couple G-spots in my life, and I’d made a lot of women very wet in doing so.  But nothing like this!  When I’d seen women squirt in porn I wasn’t sure whether it was some sort of camera trickery, or a talent only a small number of women possessed.  And now I’d made it happen!

Being a geek, I’d read up extensively on female sexual response and was aware of the debate over whether female ejaculate was urine or something else altogether.  I was pleased to learn that it wasn’t urine.  She, on the other hand, was mortified.  She apologized profusely, insisted that she’d never done that before, and hurried to get me a towel.  I did my best to assure her that she had nothing to worry about and that I was in fact totally turned on by it.  It didn’t help.  Continuing to apologize, she tried to clean me off, not that I necessarily wanted her to.  At this point I’m pretty sure she was near tears, and I went into full-on aftecare mode.  I suggested that we take a shower together, and as we huddled close under the water she relaxed a bit.  I told her how exciting it was for me, and she admitted that it was the hardest she’d ever cum in her life.  Still, I’m not sure that I ever fisted her again.

Jill’s Answer

Jack was the first person to ever fist me.  He found my G-spot pretty early into our sexual relationship, and I loved the sensation.  It led to very intense orgasms and always resulted in me squirting.  As we continued to experiment with G-spot play, Jack would put more fingers inside me at my urging.  The first time it happened he was stimulating my G-spot with two fingers and my clit with his thumb.  I asked for more fingers, and he put in the other two, and continued to use his thumb on my clit.  Eventually he took his thumb off my clit and replaced it with his very eager tongue.  As he licked me, I could feel him slip all five fingers inside me.  I felt so full, and I knew my orgasm was near.

I loved feeling his fingers undulate against my G-spot at the same time that his tongue danced over my clit.  I knew I was going to cum very quickly, but I wasn’t prepared for just how quickly it happened, and for that matter how intense the orgasm was.  I’d never felt anything like this before.  My orgasm was earth-shaking, definitely the most profound I’d ever had.  My ejaculation was torrential as well, and I soaked Jack’s face, chest, and hand with my juices.  I wasn’t expecting it, and I worried that he was going to be turned off by what I had done, but he didn’t even slow down.  It was very enjoyable, almost too enjoyable.  Definitely not something I was used to experiencing.

G-spot orgasms are my absolute favorite kind, but I can’t always handle them, and sometimes I actually cry from the intensity.  I have to be in the right frame of mind in order to relax and get the most out of them.  If I can do that, it makes it much easier to allow Jack’s fist all the way in.  Of course, I suspect that Jack loves fisting me even more than I love being fisted (which is saying a lot), and sometimes he’ll pull it out as a party trick when we are camming or performing for a live audience.

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