Endra Fulfills Some Fantasies

Kendra Williamson worked in the same small advertising firm as I did. She was in a different department, but we often saw each other around the office, and sometimes chatted over lunch in the break room. She was a real head-turner, always well dressed, usually in a medium-length skirt and a solid-colour top that brought out the delicate tones of her café-au-lait skin and dark eyes. Chatting with her over lunch, I discovered that she was mixed race, Irish/English-Canadian on her mother's side, Afro-American on her father's. She seemed to have gotten the best features of both racial backgrounds: narrow and well-sculpted nose, full but not overly large lips, and black kinky hair that she usually wore in multiple long tight braids with glittering beads worked into them.

I grew increasingly interested in knowing her better. Partly I was intrigued by her beautiful and slightly exotic appearance, but I was also attracted to her warm, easy personality that made me feel comfortable with her from almost the moment we first spoke. She seemed interested in me as well, which helped assuage my natural shyness around women enough that one Wednesday afternoon I asked her, "This Friday after work, could I take you to dinner?"

Without hesitation she said, "Yes, that would be lovely." My stomach unknotted. It had taken me a while to work up the nerve to ask her out, and her unhesitating acceptance put me at ease immediately.

When Friday finally came around, she went home to change, and I picked her up at seven. When she opened the door, she looked even more attractive than she did around the office. She wore very restrained but effective makeup that brought out the shape of her eyes and lips, and had added a silver necklace to her tastefully cut top that was low enough to be interesting without being too immodest.

She had suggested that I choose the restaurant, so I took us to one of my favourite Thai places. It turned out that she was very fond of Thai, but had never discovered this one, so it seemed I had made a good choice. Over dinner and a shared bottle of wine, she revealed herself to have as warm and engaging a personality as she had displayed at the office. She was as good a listener as she was a talker, and had soon pumped out a highly abbreviated story of my life.

After dinner, we went back to my place for a drink or two. We sat together on the couch, and I could feel her hip touching mine. My cock, which had been at half-mast all evening, was suddenly starting to swell, and I pressed my hip just a little more firmly against her. She set her glass down on the coffee table, took mine and set it beside hers, leaned over, and planted a lingering kiss full on my lips, her mouth slightly open and her tongue touching my lips gently. I returned the kiss firmly, and soon we were kissing passionately, our arms around each other and our tongues eagerly exploring each others' mouths.

I took her right breast in my hand, lifting and squeezing it gently through the thin material of her blouse. I could feel her nipple harden inside her clothing, and I ran my other hand tenderly down her neck to the neckline of the blouse. She covered it with her hand, not to stop it but to press it warmly against her skin.

This was real, and was more than I had dared to hope for. I stood up, and she stood up with me and walked with me hand in hand to the bedroom.

She crossed her arms and pulled her satiny top up and over her head, lifting it high to get it free of her cascade of dark braids. Her silver necklace tinkled faintly as it settled back against her chest.

She turned, offering her back to me to make it easy for me to unfasten her lacey beige bra. As it fell away, I slid my hands up to hold her breasts, the nipples now rock-hard. She turned back around and let me admire them, their skin a dark creamy colour with nearly black areolas. They were big enough to be substantial without being big enough to droop in the slightest -- my favourite size and shape of breast. I took the generous nipple of her left breast between my lips and moved my tongue in gentle circles around it as she sighed and laid back on the bed, her glittering bejewelled braids spilling across the white pillow.

I pulled my shirt off and bent down toward her. As I moved my lips to hers and then started sliding them back down her neck toward her chest, she looked up at me, smiled, and said, "Before we go further, there's something I'd like you to do for me."

I paused and waited.

"Tie me up."

I wondered if I had heard correctly. That was absolutely the last thing I expected her to say, and I somewhat stupidly stammered, "What?"

"Tie me up," she repeated. "I love being tied up. I don't like pain, so please don't go there, but I cum three times as hard when I feel totally helpless and at someone else's mercy."

This couldn't be happening. I had often indulged in bondage fantasies in which I had a woman trussed up and helpless while I had sex with her in various ways, and had even tentatively suggested it a few times to women I was dating, but had never been taken up on the idea. Once or twice, even the suggestion ended the date right there, so I had given up even hoping to have it happen. Now, here it was, being offered to me on the proverbial silver platter.

She waited patiently as my mind raced. Since bondage had always been totally in the realm of fantasy for me, I had absolutely no bondage equipment. Yes, I've read the "Fifty Shades" series (twice), and I knew that you can do a lot with neckties and such, but I thought I should be able to do better than that.

After half a minute or so, I said, "I'll be back," and walked downstairs to the closet where I keep miscellaneous household maintenance tools and supplies. I came back with a roll of duct tape and a pair of scissors.

She smiled and rolled over on her belly, arms at her sides, waiting to see what I would do with it. I took her wrists and crossed her arms, one wrist to the opposite elbow, cut two long strips of tape, and wound them several times around each wrist, pinning her arms horizontally across her back. This simple bondage position, which I'd seen on more than one bondage porn video, kept her hands immobilized and out of the way more effectively than just taping her wrists to each other would have done.

I let her roll back to face me. She tested the tape and found it unyielding. I reached down and unfastened the narrow black belt around her fashionable short grey skirt, and she arched her back and lifted her bum slightly. She wasn't wearing panty hose, just a lacey pair of brief panties, more than a thong but certainly skimpy enough to be incredibly sexy. I hooked my fingers in the elastic around the waist and began to slip them down. She lifted her bum again, then raised her legs off the bed so I could slip them all the way down, over her perfectly pedicured and silver-polished toenails, and off. Her vulva was shaved clean, and her pussy lips were visible just above the V of her legs, extending a short way up her mons.

I wadded up the panties, then hesitated. I wasn't sure just how far she wanted to take this bondage thing, and didn't want to spoil the mood by going too far too fast. But I decided that it wouldn't hurt to find out how far she was willing to go. I held the wadded-up panties in front of her mouth.

If she had turned her head away or even just kept her mouth shut, I would have simply laid them beside us on the bed and moved on. But she opened her mouth wide, and didn't resist when I pushed them in, tucking the last bits past her lips with my thumbs. She closed her lips over them and kept them there while I smoothed another piece of tape over her mouth, long enough to cover her face from ear to ear without getting into her hair. I placed a second strip higher, overlapping the first but coming up to just under her nose. A third went lower across her face, almost to the bottom of her chin. That was plenty: those panties were not coming out any time soon.

She worked her lips a bit under the tape, and let out a satisfied-sounding "Mmmpph" through her nose. I guess she wasn't kidding when she said she loved being helpless and at someone's mercy. The sight of her gagged face was an incredible turn-on for me, too. It pushed my feeling of being in total control to new arousing heights.

To finish the picture, I knew I had to do something with her ankles. In porn videos, the usual thing is to tape them together, and maybe add more tape around knees and thighs. This had always seemed a stupid idea to me. I was going to want to explore that pussy, sooner rather than later, and I had no intention of imprisoning it out of reach between her thighs.

I had an idea. I stood up, went to the hall closet, and came back with a broom. She looked slightly anxious as she speculated on what I was going to do with it, but I wasn't interested in using it as a weapon. I unscrewed the broom part and laid it aside, and taped the bare broomstick to one ankle, using several turns of tape so it couldn't slip. Then I taped the other end to the other ankle.

That was perfect. It was a pretty makeshift spreader bar, but it kept her legs well apart and allowed full access to the body parts that I had designs on. She evidently approved, because she laid back and wriggled her body in what looked and sounded like contented pleasure.

I shucked off my pants and underwear, releasing the cock that was now rock hard with anticipation. I couldn't kiss her on the lips any more, but I kissed her on the neck, then slid my lips slowly down her body. I stopped at her breasts again, giving each lots of attention with my lips and tongue. While I did that, I reached a hand down to explore her pussy.

It was already soaking wet, which didn't surprise me considering her obvious interest in being fucked good and proper while taped up. The musky smell of her arousal filled my nostrils, doing an excellent job of what it was supposed to do -- be a male attractant. I ran my fingers between her pussy lips and over her distended clit, rubbing the entire area and finally running a finger in and out of her vagina. Her breathing was quickening, and I could hear muffled squeals of pleasure from behind the tape gag, so I took that as encouragement to do more of same. Although I kept coming back to her vagina and clitoris, I explored her entire pubic region, including running my fingers, now well lubed from her pussy juices, around the outside of her anus.

As soon as I did that, I felt her stiffen and take a deep breath. I looked at her face to see if this was a "cut that out" signal, but what I could see of her face seemed to be saying the opposite. I ran my fingers around her asshole again, and she leaned her head back and closed her eyes with what could only be interpreted as pleasure.

I went back to her pussy and got a good fingerful of her own natural lube, then moved back to her puckered hole and gently inserted my finger to the first joint. Her breath hitched as soon as I did that, and she moved her bent knees, already spread by the broom handle, even farther apart. I pushed again and got the finger almost all the way in, feeling her sphincter clench down hard on it.

I gathered my courage one more time and asked straight out, "Do you enjoy anasl?" By way of reply, she nodded and made an affirmative "Mmmm hmmm" noise.

Talk about unexpected treats. Anal sex was another of my fantasies, but I've never happened across a woman who said she liked it. Whenever I had moved my hand further down from a woman's pussy to her asshole, I had always gotten a polite but firm "no." Now here was a woman who was eager to fulfil both my fantasies: bondage and anal.

I worked my finger in and out a couple more times, but I could feel the pussy juice drying out already, and I saw her wince from the friction the last time I pushed it in. I obviously needed a better form of lube. I slid off the bed and looked in the bathroom cabinet. I have a lot of trouble with dry skin on my hands, the kind that ordinary hand lotion doesn't do much for, so I buy a particularly thick and goopy kind of dry skin cream. If ever a body part needed thick and goopy cream, this was certainly it.

I walked back to the bed, my almost painfully erect cock wiggling in front of me. I reached between her spread legs and put a big dollop of cream on her asshole and worked some in with my finger, trying to massage gently to get it in as far as I could. She nodded approvingly. My cock ached to be rammed in that tempting hole right now, but I held back. I wanted to make sure she was good and warmed up, her pussy stroked to fiery heat so that she would be half-way to an orgasm before I tried to finish it off with my cock up her ass.

I considered rolling her over on her belly with her ass in the air. It would have been a more convenient position for anal sex: I wouldn't need to keep her legs rolled high up to expose her back passage, and I wouldn't have to work around the makeshift spreader between her ankles. But I knew from diligent research on porn videos that she would be equally accessible from the front, and I liked the erotic potential of being able to watch her breasts and her beautiful face -- the part I could see of it, anyway -- as I was drilling her ass. And I also wanted to keep an eye on her face to gauge her reactions as I worked my cock into her. Her face would tell me if I was going too fast or was hurting her, or if she needed more stimulation to work up her erotic arousal. I wanted us to work together on this, my first real-life excursion into this unknown territory.

I left her spread feet on the bed for now, her knees bent to give me easy access to her erotic bits. I worked on her pussy for a while, two fingers massaging the inside of her vagina and a thumb on her clit. Her breathing deepened further and she was still making little squeaks of pleasure behind the gag, so I knew I was on the right track.

She had said that she gets hugely turned on by being bound and helpless. I was also getting incredibly turned on by being so fully in control, playing her body like a musical instrument and pulling erotic arousal from it with my hands in her pussy and my lips on her nipples. I could feel my orgasm mounting in gentle waves in rhythm with hers, but I tried not to let it break too soon. I wanted to finish off inside the new territory of her waiting asshole.

Finally we were both ready. She was hovering on the edge of orgasm, and so was I. I pushed the broomstick up and back, and her hips rolled up to give me a straight shot at her anus. I took my other hand away from her pussy for a minute so I could put another fingerful of cream on my cock and then guide the tip to her waiting hole. I pressed, and her sphincter resisted at first. I pressed more firmly, and was rewarded by the tip slipping past her sphincter. I saw her wince with momentary pain as I forced my cock past her opening, but it cleared as soon as I was inside and her sphincter settled into its new role of being stretched around my penis.

I laid still for a minute, only the first couple of centimetres inside her. I wanted to give her anus time to adjust to being filled, and also to relish the sensation of being gripped by a hole tighter than any vagina I'd ever experienced. But then it was time to dive deeper.

For once, I was glad that I had a perfectly average sized cock. I wouldn't have wanted to try to force a giant pornstar cock up her ass, at least not until I knew her likes a lot better. I began making slow, short thrusts, each one a little deeper than the one before. Her firm grip moved up from my glans to the shaft of my cock, moving up and down with each thrust like a circled finger and thumb pumping my cock in a firm hand job. Lacking Kegel muscles, her rectum itself didn't have any grip, but the firm grip of her sphincter more than made up for it. I quickly found that the best way to achieve sensation was to pull back until only the last few centimtres of my penis were inside, and then slide back in until I was balls-deep inside her, the firm grip sliding along my shaft in a powerful anal massage.

Her breasts rolled up and down on her chest with each thrust, the sight increasing my own arousal. Now each thrust was nudging a loud "Mmpphh" of pleasure out of her. Her head was rolled back and her eyes were shut tight as she concentrated on the sensations in her anus and rectum. I returned my hand to her pussy to give her some extra stimulation, and was rewarded with even stronger pleasure noises. Her arms pulled instinctively at the tape that held them behind her back, and the resistance it provided seemed to be nudging her to new heights.

Finally she arched her back and let out what would have been a wall-shaking orgasmic scream if it hadn't been for the gag. I could see a major advantage of the gag: it allowed her to let loose as loudly as she wanted without alarming the neighbours. Even with her mouth taped, the scream, redirected out her nose, told me the intensity of her anal orgasm.

I held my hand and my cock still while the orgasm subsided. The wild panting breaths through her nose gradually subsided to deep, rhythmic post-orgasmic breaths of satisfaction, and I began thrusting again. This time I concentrated on my own building arousal, focussing on that phantom grip sliding up and down my cock to massage me to what promised to be the orgasm of my life.

She helped by thrusting her hips in time with mine, driving my cock ever deeper and more firmly into her on each stroke. Her face told me that I could thrust as deep as I wanted without hurting her; in fact, she seemed to be enjoying vicarious pleasure as she watched my face react to my building arousal. I held her hips tightly with both hands, the whole world contracting to that incredible sphincter grip on my cock as I felt it pulsing its way to ejaculation. I let myself go, fully immersed in the sensation of my cock pumping squirt after squirt of cum deep into her body.

I laid on her belly, my spent cock still inside her as I came down from the endorphin high of orgasm. Finally, it was totally limp, squeezed empty by the unfamiliar, exciting sensation of being up a woman's ass for the first time in its life. I reached awkwardly for the box of tissues on the night table -- I should have been better prepared for this part -- and pressed a handful to her asshole as I slipped out of it, catching the cum that started to ooze out before it made a wet spot that we would be avoiding for the rest of the night.

When I looked at the soggy tissues once they had done their job, I noticed that they were only soaked with cum. There was no brown mixed in with the liquid that leaked out of her. I supposed that part of her work in getting ready for our date, in addition to changing her clothes and fixing her hair and makeup, had been an enema. I certainly could have lived with a little poo as part of the process, but I was also impressed at her foresight. She was obviously a pro at this anal sex business.

I carefully peeled the tape off her mouth and received the thoroughly soaked panties as she pushed them out with her tongue. I tossed them in the general direction of the laundry hamper, missing and leaving them in a pile on the floor -- a quick run of laundry would obviously be the first order of business in the morning.

Once her mouth was free, I leaned in for a long, passionate kiss. When we broke the kiss, she took a deep breath through her mouth, the first she'd been able to take for quite a while, and then said, "Fuck, Kev, that was absolutely great. Is this the first time you've done anal?"

I confessed that it was. "You fulfilled a boy's biggest fantasies tonight."

"Well," she replied, "you're a fast learner. You did everything right to make it a great experience for me too."