(This piece was originally performed at Bedpost Confessions in January 2011. It was a bit strange to get up and tell such a vulnerable story one week after I had asked my husband for a divorce, but hey, I apparently like to live on the edge…)
Friday evening, and I was bored. Earlier, I had met a guy at the Jackalope who had chatted me up online that morning. We had a couple drinks, sat in his car on 6th street and smoked a joint and went back to the bar. I walked in the bathroom, walked back out and told him I was going home. I had no idea that I was going to do that until the words came out of my mouth, but there it was. I could have easily taken him to bed, but it didn’t seem worth the effort.
Wanting some amusement, I decided to put an ad on Craigslist Casual Encounters women seeking women section. Now, I am sadly, inexplicably and hopelessly a straight girl. Don’t get me wrong: I absolutely adore women. Sometimes i’m even sexually attracted to them. But when we actually start kissing, it’s kind of like two magnets repelling each other. There is, however, one sex act where women are the logical choice: fisting. Because their appendages are usually smaller than a man’s, they are hands down better (pun intended). So on this particular Friday evening, I put up an ad, with the headline, “Fist Me. Please.” I described myself, explained that I was straight and why I was seeking a woman.
I checked my hook-up email account 30 minutes later, and found half a dozen responses…from men. Apparently women in my city don’t spend much time on Craigslist Casual Encounters, and who could blame them? My past forays in Casual Encounters had netted me dozens of clueless bottom feeders. I’d love to find out how many of them have had Angelina Jolie show up at their houses at midnight on a Friday after she answered their ad.
I perused the answers, and sent a short email back to some of the guys. What is your experience level with this activity? Can you host? Are you willing to meet in a public place? Will you respect my boundaries? Several of them responded well, but then started asking me for other things. Nope, sorry. I’m not interested in reciprocating, and no, I don’t want to have sex with you. I want this specific fantasy fulfilled, and that’s about it. One guy seemed pretty nice, but he wasn’t available on Saturday afternoon; naturally he asked if I would come over immediately. Um, NO.
Saturday afternoon I got a couple more new emails, and tried to avoid getting into prolonged conversations with these guys. At this point, I was feeling fairly annoyed by the whole process. Perhaps I should have fingered my delete button a bit more.
On Sunday, I got an email from a guy who said fisting was a huge fetish of his. He was coming to town on business that week and was happy to host, and he didn’t want me to reciprocate. He was friendly and nice, and had good communication skills. I wrote him back, asked a bit more about his experience level, and sent him the requested photo of myself.
And then, he did the most amazing thing: he sent me a picture of himself, with his clothes on, and NO PENIS anywhere to be seen.
Please allow me a brief rant here on guys trying to hook up. Despite how many times they read that women don’t want to see pictures of their dicks, they insist on sending them. My theory is that they strike out so often that this is the only way they will ever get a woman to see their penises. Don’t get me wrong – I love dick, and have been known to fall on my knees and drool when a man unzips his pants and reveals a beautiful cock, but honestly, I’m much more interested in what your other head looks like. I’m not a porn watcher, and am unlikely to be turned on by the mere sight of your throbbing manhood. But alas, they just don’t seem to get it.
End of rant.
I’ve decided that I like this fellow, and we get out our respective calendars and agree to meet the following afternoon for lunch because he wants to make sure I’m not a psycho. I call to make the arrangements. On the phone, he suggests that perhaps if we like each other, after lunch we can climb into the back of my car and I can pull up my skirt so he can have a little look-see. Nice!
I show up at the restaurant, and he is sitting near the window. We greet each other, order our food, and sit down at a quiet table. He tells me he is surprised that I showed up.
The first thing I notice is that he’s wearing a wedding ring. I myself am married, but my husband and I are openly non-monogamous. I don’t do cheaters, though, so I grill him about the status of their marriage. He has told his wife about contacting me. I tell him that he must get her explicit permission, and that if she says no, the deal is off.
The second thing I notice is that his hands aren’t exactly small. The last male partner I had who was able to fist me was a little guy. My husband has tried, repeatedly, but his hands are about the size of the Texas panhandle, and there’s just no way it’s gonna happen. I’m skeptical about my new friend, but he assures me that it is possible with the proper combination of time, lube and relaxation.
We talk more about our past experiences with fisting, discuss our respective STD histories, and swap info on our relationships. He’s a sweet guy, and seems honest. By the end of our lunch, I’m ready to spread my legs and let him stick as many of his gloved fingers inside of me as he can manage. I have tentative plans for the evening, but cancel them. He texts me and tells me he’s gotten the go-ahead from his wife and we arrange to meet up after work.
The remaining couple of hours of my work day are filled with nasty text messages and emails. I ask him if it’s okay masturbate when I get home, and he say yes, but send some pictures. It’s difficult with the camera phone to get the angle right without being able to see it, but I manage to send him a few beautiful shots of my genitals with my pyrex dildo sticking out from them. Finally, it’s time to head for his hotel.
He’s gotten a room with two beds; I suspect that by the time we get done, things will be messy. We chat for a few minutes, and try to establish our boundaries. Because there will be no intercourse involved, it doesn’t feel appropriate to kiss or snuggle. We are about to leave for dinner, but instead he pulls down the sheets on one of the beds, throws a towel down, stacks up some pillows for my back, puts on a glove and asks me to lie down. I oblige, and he sits down between my open knees and begins sliding a couple of fingers in and out of me, looking into my eyes. I moan and wiggle, open my legs further, trying to accommodate more of him. He pours more lube out, and continues to try to push more of his hand in, working four of his fingers and part of his thumb into me. I’m feeling very turned on. And then, he stops, pulls off the glove and tells me it’s time to go get dinner. I try not to pout. I want him to keep going, and he knows it.
We grab a light meal. During dinner, he tells me about some of his own experiences of being fisted. He has spent years working to stretch out his rectum to accommodate a hand. It makes me feel better to know that he has been on the receiving end of this sort of extreme play. We’re laughing and joking like old friends by the time we head back for the hotel.
It’s been a hot August day, and I want a swim, so we suit up and head out for the pool. My friend pulls me close and starts gently rubbing my crotch through the swimsuit and tweaks my nipples while we’re talking. Suddenly I’ve had enough of swimming, and suggest we get out of the pool. Now.
In the room, we adjust the A/C to make it a bit warmer, strip off our clothes, and assemble supplies: towels, gloves, three different kinds of lube, pillows, my trusty Hitachi Magic Wand with its “God Masturbates” sticker on it. I lie down on the bed with my knees apart, and he sits between my open legs again. He pours huge quantities of cocoa butter lotion on his hands and my genitals, and starts working his fingers into me, first two, then three and four.
A big smile comes over his face as he works on me. “I love doing this,” he purrs. “I could do it all day long, every day.” His fingers twist and push as he tries to get me into that space where I’m both aroused and relaxed. He starts going back and forth from hand to hand, putting one set of fingers in while the other is on its way out. His hands are sideways, and as they meet it looks quite a bit like he’s praying. I suppose, in a way, he is. He continues working me open with both his hands like this for about 30 minutes. I lie back, eyes closed, enjoying the sensations, willing my muscles to relax more.
He squirts more lube on his right hand, curls his thumb into his palm, and presses and twists. I yelp in discomfort, and he backs off. But the relentless pressure is causing me to loosen up some, and he presses his hand in again, trying to get it past the second knuckle of his thumb.
He has been staring into my eyes, staying very present with me. We are engaged in an act that is, in many ways, much more intimate than intercourse. I have long held the belief that every man should get fucked up the ass at least once (by a woman with a strap-on, of course) so he can understand what women feel like when they allow a man to get inside their body. So much trust required to cross that particular boundary. This one seems to get that.
As we get closer, he begins to talk dirty to me. “When I finally get it in there, I’m gonna fuck you with my whole hand, and you’re gonna come so hard. You’re gonna love it so much, I’m going to turn you into a fisting slut. You will be begging me for it.”
I moan, and start rubbing on my pubic bone, stimulating my g-spot from the outside. “Yes, please. You can tell how bad I want your whole hand in there.”
He pushes some more. “Yeah, I know you want it. Don’t worry, we’ll get there.” He gives a really hard push…almost. The pressure is too much. I gasp, and he backs off again.
I grab my vibrator and tell him I’m going to get myself off. He continues moving his hand back and forth, pushing up so that i’m getting g-spot stimulation from both the inside and the outside. I feel my vaginal muscles tense and begin to contract. It’s a wonder I don’t break his fingers. I come quickly, and switch off the vibrator.
Perhaps this wasn’t the best idea. The orgasm has made me sensitive, and we decide to take a break. I empty my bladder, and grab some water and a snack.
We start back up again after 15 minutes. My pussy is feeling sore and swollen, and the latex from the gloves is beginning to rub me raw. I ask him to gently massage the sides and bottom of my vagina to get it to relax. He puts his hand in as far as it will comfortably go, and holds it still. I can feel tiny little orgasmic tremors as my pussy starts talking to his hand, but when he tries to push any further, my body says no.
He removes his hand. “You’ve had enough for the night,” he says, while taking the gloves. “Your pussy needs some time to think about what it’s experienced.” He comes back over to the bed, and kisses me on the cheek. “You did really well.” He hands me some chocolate.
“Thank you,” I murmur. He lies down on the bed next to me, and we face each other, bodies apart. I put my arm over his side, and ask him if it’s okay to touch him like this. I know I’m feeling a bit distant, having a difficult time bridging the gap back to being strangers in a hotel room, and suspect he feels the same.
My body begins to feel a little shocky, and it’s a school night. My friend needs to call his wife and baby and say goodnight before it’s too late. I walk through the hotel lobby, carrying my gym bag full of goodies, smiling to myself and hoping the desk clerk doesn’t notice me leaving.
We got together and played once more, but after he got home, I got a nasty text message from his wife. It turns out he had lied to me about having her blessing, and that was the end of that.
My husband has continued to try to push his extra-large hands inside of me. It’s fun, but still unlikely to happen. I will wait patiently until I find my Mistress Fister. But that’s a story for another day….