It wasn’t my first time in bed with a man, but it was my most fun. Gary didn’t have many hang-ups, and he was usually into trying whatever I could dream up. I enjoyed myself so much that when he asked to be exclusive, I agreed. Our only problem was that Gary worried all the time that I might leave him for a woman.
Maybe because he first caught sight of me while I was on the dance floor copping surreptitious feels under my girlfriend’s halter top, Gary couldn’t seem to trust that I was fine with staying faithful to him.
He constantly asked me, “Don’t you miss pussy?”
I really tried to explain. I’ve eaten plenty of pussy in my life. I like it, but it’s not like I’ll die of pussy-thirst if I don’t get any. Dick is nice, too, and when I was with my girlfriend, I didn’t have any of that. Being exclusive with somebody always means giving something up.
Still, Gary persisted. It started to sour what was otherwise a very nice relationship. Finally, one night, I decided to tell him the truth. There was something I missed from being with women. I’d held it back so as not to feed the fire, but by then I felt I had nothing to lose. I thought maybe he’d gotten so worried because he could sense I wasn’t sharing everything.
A perfectly good evening in bed had devolved into yet another tiresome line of questioning about the pleasures of cunnilingus. I sat up, crossed my legs, and looked Gary in the eye. I said I’d tell him what I missed from sleeping with girls, but if I did he wasn’t allowed to ever bring this topic up again.
He quickly agreed, so I took a deep breath and told him. Fisting. I missed having some girl’s arm buried in me practically up to the elbow. I told him nothing could ever compete with the way it feels to have somebody that deep inside me, so far that it feels like she’s right in the middle of my lungs; that my heart is pounding around her hand.
I feared Gary might get depressed now that I’d confirmed his fear that I missed having sex with girls. Instead, he just smiled.
When I asked him why, he wiggled his fingers at me. He said he didn’t have a cunt, but he did have a hand.
I stared at his big, callused hands in horror – Gary hung drywall during the day. I told him I didn’t think they’d fit inside me. He countered that it couldn’t hurt to try. The idea of taking his whole hand scared me, but I have to say I also felt curious about whether I could do it.
After a few minutes’ hesitation, I agreed. I told him we’d need to start by buying about a bucket of lube and some vinyl gloves for him (I don’t like latex).
He was very excited to try this the very next weekend, and best of all the plan made him stop annoying me with endless questions about girls. That Saturday, I took a long bath before Gary came over and generally tried to get myself as relaxed as possible.
He showed up with a single red rose and a paper bag full of the supplies I’d asked for. I laughed and let him in. He wanted to know how many girls had gotten their whole fists into me. I don’t like to share my personal statistics, so I shot back, “Every one who’s tried,” and left it at that.
We got in bed and made out for a while. Gary was a good kisser, but he was even better at playing with my nipples. I took off my bra, and he sucked and nibbled them until I started humping his leg. Then he asked if I was ready for him to try fisting me.
By then, I was definitely ready to get something into my cunt. I had him pull three chairs up to the edge of the bed. I used two of them to prop up my legs, almost like the stirrups at the end of a gynecologist’s table. I told Gary to pull the third chair between my legs. That one was for him to sit on. I told him to get comfortable, because with hands as big as his, working one into me would probably take a long time. Then I rolled over to get my wand vibrator out of my nightstand. Gary asked if I thought his fist wouldn’t be enough for me. I explained I’d need the vibrator to help me open up enough to get him in.
We made a little awkward conversation. Even though I’d obviously done this before, it had been a while and I was nervous. He made jokes about tickling my ribcage from the inside, but I could tell he wasn’t sure how he would actually fit, either.
I wanted to get things going before either of us got keyed up anymore. I switched the vibrator on and started going at myself. I knew Gary liked watching me masturbate, and I made a bit of a show out of it, bucking my hips and gasping a lot more than was strictly necessary. It was good for me to do that, too, since it made me feel sexy. I switched the vibrator off when I was still a long way from coming and told him to go ahead and start working his fingers in.
Gary dropped whatever we’d been chatting about before, snapped one of the vinyl gloves onto his right hand, pumped a bunch of lube onto it, and got to work. I’ve always been able to take two fingers pretty easily, so we wasted no time getting to that point.
He fucked with me a little in the process, curling his fingers up into my G-spot until it almost hurt. I panted and writhed and gave him dirty looks. I told him to quit screwing around and shove that third finger in. He shoved it in so hard I yelped, then gave me an innocent expression.
I leaned up so I could smack him but stopped short when I saw what was going on between my legs. His three fingers already made me feel full, and he had a whole bunch of hand left to go. I couldn’t imagine how he would ever get that whole thing into me.
Gary let me stare in awe for a little while, then asked if I was OK. My insides shivered and my cunt clenched. I didn’t know how this was going to work, but more than ever I wanted him to try. I lay back and told him to keep going.
He suggested I turn the vibrator back on, which I did. I’ve got pretty good muscle tone inside my pussy – one of my girlfriends was really into exercising there and got me into the habit. My vibrator is powerful, and when I put it on my clit full force, it made me tighten up around Gary’s hand so hard he actually grunted.
It was my turn to ask if he was OK. He said he was, he just needed more space, and the next thing I knew he spread his fingers out inside me. I shrieked. The girls who had fisted me probably hadn’t been strong enough to fight my cunt muscles that way. It felt strange and intense to be spread open like that when my pussy was bearing down so hard.
By opening up a little space, Gary also made me want to be stuffed even more. I told him to put another finger in.
He withdrew his hand and I heard the lube pump. Then he prodded at my entrance. This time, I could really feel the stretch as I took four of his fingers. I turned the vibrator up to a higher intensity, and Gary eased his fingers in bit by excruciating bit.
Then the bones of his hand hit me. They covered way too much area. “I don’t think this is going to work,” I told him.
Gary asked if he could just try a little. He promised to stop right away if anything felt uncomfortable to me. I took a deep breath and nodded.
He said he would start by just fingerfucking me. That sounded good, and I hadn’t come yet, so I agreed, then went for it with the vibrator. When I’m stretched really wide, it feels great, but it’s hard for me to come. When I do come that way, however, it feels amazing. I come about ten times harder than normal.
So, I felt pretty motivated to take myself to the point of orgasm.
Everything had gotten so sensitive that I could only stand to use the vibrator for short stretches. I’d roll it onto my clit and it felt like every muscle in my body would spasm. I’d sort of rock and jerk for a minute, then switch the vibrator off again and pant until I caught my breath.
After a few rounds of this, I noticed Gary watching with a silly grin on his face. When I asked about it, he said it was hot to watch me push my chest up and make my breasts jiggle. I told him I was glad to be keeping him entertained, then went back to what I was doing.
The vibrator on my clit felt great, and so did his hand in my cunt. Still, my orgasm eluded me. I kept getting distracted wondering when he’d try to push more of his hand inside. It had me a little tensed up. It didn’t matter that I was soaking wet and turned on as hell. I couldn’t get the mental rel
axation I needed in order to come.
Eventually, Gary noticed I’d started groaning from frustration rather than pleasure. I was pretty incoherent by then, but I tried to explain how much I needed to come and how I couldn’t quite get there. This probably sounded more like, “Fuck. Come. Now. Need.” I won’t apologize, though. I don’t think anyone would do very well at talking with four of that guy’s huge fingers shoved up her cunt.
Gary took the vibrator from me with the hand he still had free. It was hard to let go of it. I’d kind of wrapped my hand into a numb claw around it, and my fingers didn’t want to work.
He put it on a higher setting than I normally use and pressed it to my clit much more directly than I could or would have. I yelped and would have scrambled away except that he just slightly curled the four fingers inside me, which made me freeze. I still can’t say for sure whether it hurt or felt like the most amazing thing ever. In any case, I wasn’t going anywhere.
I couldn’t close my mouth or do anything. I think I started to drool.
He muttered something about transferring the vibrations to his hand. I have no idea what he was getting up to. What I know is that whatever he was doing made it feel like some sort of pleasure vise had me by the cunt. Vibrations and sensations pressed me from two directions, so my clit ended up trapped between the vibrator on one side and the pressure of his hand on the other. It was more than I could take – so much more that I’m not even sure I could call it pleasure – but I didn’t want it to end.
He added more lube, then started to really push. I started to tell him again that I didn’t think this would work, but didn’t make it past the first sounds of the words. Pretty much immediately, all I could do was moan louder than I ever had in my life.
When I’d been fisted before, I had to focus on relaxing the muscles in and around my pussy to make room for the hand that was entering me. This time, I was so overwhelmed by sensation that I didn’t have it in me to even think about particular muscles, much less try to control them.
Little by little, the bridge of his hand pressed through my body’s resistance and into me. Every time I was on the verge of asking Gary to stop, some little twitch or pulse would hit my nerves with indescribable intensity and I’d decide to hold off for just a little more.
I couldn’t say how long this went on. It seemed like hours. I felt like a tiny animal, hot skin, hot breath, hot blood speeding through my body at an insanely fast pulse rate. Gary’s enormous hand became my only reality, the only thing I could think about. If I’d opened my eyes, I don’t think I would have seen anything. That hand was taking up all the room in both my body and my brain.
Then Gary made a strange sound, sort of like a gasp but softer. I lay still for a moment, filled to the point that I could do nothing but receive. He didn’t need to say anything to let me know he’d gotten through – I could feel the change in the room itself.
When I could manage it, I lifted my head. He gazed at me with a tender, attentive expression that made me wonder for a moment what it would be like to give birth to a child. Then he shifted his fist just slightly and those thoughts dissolved into utter lust.
I put my hand on my bare stomach. I could feel the shape his hand made inside me. I could feel his whole fucking arm. I couldn’t believe he’d gotten it all in.
I collapsed backwards onto the bed. He never let up with that damn vibrator, and I thought my head would explode. His fist rocked inside me. He squeezed it rhythmically so it felt like a much calmer heart than the one in my chest, sending pleasure through me as it beat.
My cunt had stretched so wide I didn’t know if I could come, but I didn’t have the energy to do anything more than give in at that point. I remember flailing my head against the pillows like I’d been possessed by a demon. My hands moved, too, grabbing at my breasts, my stomach, my legs.
Then Gary began to twist his arm inside me – again, just slightly, but given how intense everything felt, it was enough to make my stomach flip over. I grabbed the vibrator back from him and nudged my clit with it.
I wanted to fuck him, but I couldn’t really move. I felt pinned in place. Instead of fighting the way I felt, I used all that energy to apply the vibrator to my clit. I grabbed the vibrator with both hands so I could control it better.
Gary wrapped his free arm around one of my thighs. I tried to hug him with my other leg. We rocked together and everything felt excruciating right up until the moment that it turned into this shattering, agonizing orgasm that felt like it was going to shoot out the top of my head and the tips of my toes at the very same time.
If I’d thought it was hard to take his fist, it was even harder to come around it. My cunt ached as it pulsed, and I couldn’t have stopped screaming for anything. I’ve heard of people passing out during fisting and always thought that was an urban legend. I can’t say if I passed out that time, but there are a few seconds I can’t remember.
At some point, I finally stopped thrashing and crying and coming, and I remembered Gary again. “I didn’t break your arm just now, did I?” I asked.
He chuckled and said not quite. Then he asked if he could take it out – according to him, the inside of my cunt felt hotter than a sauna.
I said OK, and he tugged. I yelped and told him to go as slowly as possible.
He tugged some more, a little gentler, then grunted softly.
I lifted my head. It was still disconcerting to see his arm coming out of my cunt, especially since I wasn’t used to getting that view with someone so thick and hairy. He told me he thought he was stuck.
Even weak from coming so much, I had to laugh a little at the barely restrained panic on his face. I explained about the vacuum seals that can form around a person’s wrist when a woman comes really hard while being fisted, and told him how to use one lubed-up finger to break the suction. He did as I instructed, and we were able to ease his hand out of me.
As soon as he got free, he collapsed next to me on the bed. He wanted to know how well he’d done.
I teased him, telling him it had been sort of OK. Then when I saw he was still insecure, I gave him the serious answer. I told him I’d never had anything that large inside my cunt before, and outside of childbirth didn’t expect to ever have anything that large in me again.
“Does that mean you didn’t like it?” he said.
I told Gary I’d liked it very much, I just thought I might die if we tried it a second time.
We both laughed and kissed each other, and everything felt like a big relief. After coming like that, I always want a long nap. Just before I slipped into unconsciousness, I checked to see if we’d alleviated his worries that I’d leave him for a girl. After all, I told him, everybody’s got a fist.
Gary did stop asking me if I missed girls. We were together for two years after that. I still remember him fondly.
A Commercial Arrangement
Sean, Chester
I count myself as incredibly lucky. In some ways, that is. I suppose I’m not lucky from the point of view that I can’t get fully turned on unless I pay for my sex. I have no idea exactly why that is, but it probably stems from my teenage years (don’t most things) and I have to blame my father. Maybe that’s a cop-out but that’s what I think.
On the occasion of my sixteenth birthday, my parents took me and my twin sister Louise to Thailand to celebrate. It was only the second time I’d ever travelled abroad (the first was Mallorca) so it was pretty cool to be going so far. I have no idea whether Mum and Louise were in on what Dad had planned; I was always too embarrassed to ask.
He took me out for a few drinks in Pattaya on the night I turned sixteen. I have no idea what we drank and I’m not sure he had either, but later on in the evening he had a whispered conversation with a really sexy-looking woman at the bar and the next I knew she was leading us up some stairs. I asked him where we were going and he said it was my birthday surprise. Next thing I know this woman has opened a door and is standing aside. My father put his hand
round my shoulder and eased me into the room. In there, standing by a big double bed, was a stunning Thai girl wearing one of those long dresses with slits up both sides of the skirt. I turned round just in time to see Dad and the woman go out and close the door on us.
I was just so embarrassed and had no idea what to do. The girl was obviously used to that, though. She told me her name was Charunee (I have no idea if I spelled that right) and she took my hand and pulled me over to the bed. I wasn’t stupid and knew she was a hooker, but she sure was good-looking. She kissed, too, and I know from more recent experiences that kissing’s unusual. And I remember she smelled so good, like fresh flowers. She didn’t rush me and spent a lot of time kissing me and rubbing my shoulders to relax me. Then she just stood in front of me and gave me a vision that’s been with me ever since; she reached up to her shoulders and pulled a couple of straps, making the dress fall to the floor round her feet.
She was completely nude underneath, with not a trace of hair anywhere on her body. I remember how slim she was, too. And her cute breasts with prominent nipples just asking to be sucked, except I was too chicken to actually do it. She pushed me back on the bed slightly and fed one between my lips. I didn’t stop then, and I’ve had a thing about rubbery nipples since. Becky (my wife) has nipples like that; it was one of the reasons I was so attracted to her in the first place. But more of Becky later.
Charunee helped me off with my clothes, saying how strong I was and all that BS. I do wonder how old she was. Around eighteen, I’d guess, the older woman! But when I was naked she used her tits to massage me, all up and down my back and over my shoulders, then on my front, letting me suck her tits and sometimes holding them together around my hard-on. After a bit of that she popped me into her mouth and started to suck slowly and gently. It was bloody amazing, the best ever. Ever after I mean; I’d never had it done before then. Stupid teenage me just came in her mouth after two seconds. She just left it there, swallowing what I pumped out and licking her lips afterwards like it was the best thing she ever tasted. I thought that would be it and cursed myself.
The Mammoth Book of Urban Erotic Confessions Page 23