The Anal Virgin

I'd been seeing my new boyfriend, Sam, for about 3 months before we were comfortable enough to talk about fantasies. Now I was raised in the country on a quaint little farm on the prairies, and not that I fit every stereotype, but having only moved into the city two years ago, I was very much sexually naïve. It's not that I believed sex was only for procreation or anything like that, but the first time I ever gave Sam a blowjob, at age 33, was the first time I'd given anyone a blowjob in my life, and I must admit I felt a little guilty about it.

I'd been raised by country standards, which meant that while I was ruggedly independent, I also had it ingrained in me that the man was the boss, and indeed it made me deliriously happy to make my man happy, and to provide satisfaction for his needs. I think this is part of what made Sam court me the way he did, as he was clearly a man who still believed he should be the boss, should pay for our dinners, and should hold doors open for me. Some would call it "old fashioned". I would simply call it wonderful.

So there we were, three months into a very new relationship, when Sam made the comment that he liked that I was a little submissive in sexual terms. "I love that you do so many of the things I ask you to," he'd commented. "I love that you enjoy letting me take the lead."

I tried to explain, as best as I could... "Sam, it's difficult to put into words, but if I have any sexual need, it's to please you," I told him. "There is simply nothing that gets me hotter than knowing that you're going to have your way with me. That you're going to take your pleasure, and that it's going to be me providing that pleasure." I neglected to mention how much I loved giving him head, let alone how deprived I now felt at the previous ten years of my life, during which I'd been sexually active without having ever performed fellatio.

Sam chuckled. "Oh, you have needs of your own Jenny... everyone does. You just haven't found out what they are yet." He seemed so confident, and a part of me suspected, perhaps even hoped, that he was right. "In fact, I'll bet we could figure out what they are, if we try."

That night, Sam tied me up for the first time ever. I'd never been tied up in my life, and while it was thrilling to be so vulnerable in front of him, I had no fear of being harmed, for I knew Sam too well. He started by having me standing naked in front of him. He then produced some rope he'd had in the garage, and tied my ankles tightly together with a length of it. He then took another length and tied together my knees, just above the knee caps. While I found all of this highly erotic, I almost exploded when he proceeded to tie my elbows together behind my back, pulling them tight until my breasts were jutting out in front of me. He then tied off my hands, and proceeded to bind my breasts by wrapping rope above, below, and between them until they stood out helplessly.

Once he'd finished, he stood back and admired his work and proceeded to get undressed himself. I was a little surprised, but not unpleasantly so, to see he had a raging erection when his pants came off. I'd never seen him so hard or so big without my having even touched him.

Sam moved over and stood behind me, pressing his cock into the small of my back, kissed my neck, and played with my helplessly bound nipples. I was moaning with need within about 15 seconds. He worked his kisses down my shoulders, his hands to my hips, and I soon felt him holding my ass cheeks open and putting his cock against me there. I gasped and half hoped and was half afraid that he was going to enter me there. At age 33, I'd never had anything up there in my life, and I both wanted it and didn't want it right then.

Sam felt my anticipation and also how tense I was and worked his kissing up to my earlobe, and he whispered "Don't worry babe, I'm only going to do that when you beg me to." I was half relieved, and half disappointed. I felt like I wanted that very badly, but I couldn't admit that - it simply wasn't proper. He had to just take me!

Sadly though, he moved around to my front and played with my nipples some more, this time a bit more roughly than I'd felt before, throwing in a few pinches and twists. Enough to make me gasp a few times, but not enough to make me cry out. "Your ass I'm not so sure about. Yet, that is." he said lightly, "But I've seen how wet you get every time you suck my cock. Down on your knees. Now." I could feel myself blush intensely at his comment, as I was sure my secret was mine alone. I couldn't believe he knew how much it turned me on to give him head! He threw down a folded up towel for me to kneel on, and waited expectantly.

I obviously couldn't kneel gracefully, trussed up as I was, but Sam half helped and half forced me to my knees, and before I knew it, he was forcing me back on my heels, and I saw the biggest, hardest erection I'd ever seen on him right there in front of my face. I knew what he needed, and I knew what I wanted, and I opened my mouth and leaned forward. Sam grabbed my head and slowly began to fuck my mouth. Gently at first, but as his need built, so did his force and depth. It's not in my nature to be graphic, but soon he was fucking my mouth so hard that I could actually hear his balls slapping against my chin.

I could sense his orgasm building when he stopped about half way in my mouth. "You want to know what really turns me on?" he asked. I "mmmph"d a response around his cock. "Having a girl who will do the things you do for me. Seeing a girl incredibly hot, wet, and excited, and unable to do anything about it. And keeping her there for hours". I again "mmmm"d a response. He pulled out, leaving a string of precum hanging from my lower lip and chin down to my tightly bound breasts, and said "I want you to listen now, not talk. Nod if you understand. I nodded.

He knelt beside me and began teasing my nipples. Soon I was panting and moaning with as much need as I'd ever felt, and he moved a hand down to my pussy, which was so drenched that I could feel my juices running down my ass and onto my ankles. "I want you to say ‘Please Master' if you think you're going to cum within 5 seconds if I don't stop," he told me. I nodded my head to indicate I understood. It wasn't long before I gasped "Please Master!", and he stopped, told me I was a good girl, and moved back up to my nipples. He kept this up, alternating between my pussy and my nipples for a good half hour. I was frantic to cum, and had been on the verge several times before he'd stop and go back to my nipples. "Please Master" had almost become a mantra, I'd said it so many times. Finally, he stood up and put his still hard cock in front of my mouth. I opened my mouth obediently, and he grabbed my head, easing his cock back into my mouth as he spoke. "And after I've kept them on the edge forever, knowing that their orgasm is out of their control completely, that it's in my hands alone... " he paused his speech and continued to gently fuck my mouth for a minute. "NOT LETTING HER CUM" he said in a wicked tone of voice, and he rammed his cock all the way home for emphasis, and resumed roughly fucking my mouth.

He took several breaks, every time he got too close to cumming, and teased me during those breaks, quickly bringing me to the edge a couple of times before he'd resume fucking my mouth. He continued this for at least an hour, or thirty "Please Masters", whichever came later. I'd never seen him maintain an erection for so long. His cock was still very large, very hard, and was now very purple. It almost looked like it must be hurting him by now.

He finally stood up for the last time and fucked my mouth over and over, his balls slapping off of my chin, and I knew that this time he was going to cum. I felt his incredibly large and hard cock grow impossibly larger and harder yet, and felt the first spasm, followed quickly by a gushing of hot semen into the back of my mouth. He pushed my face tightly against his crotch, forcing his way deep into my throat, and grinding painfully as he finished his orgasm, momentarily cutting off my air flow as his cock spasmed and gushed hot semen into me. He slowly withdrew and fucked my mouth a little bit more as he wound down, finally pulling out and holding my head to his tummy, stroking my hair and telling me what a good girl I'd been. It was a lovely feeling that almost made me forget how badly I needed to cum. Sexual need aside, I was as happy as I'd ever been at that moment. I'd never felt so desired or so needed in my life.

Eventually, after he caught his breath, he spoke again. "I'm serious about you not cumming" he said. "If you really want, though, I can make you cum right now, but I just wanted you to know what my fantasy is." I only considered this for a minute before opening my mouth, then pausing before asking if it was ok for me to speak now. Sam knelt down in front of me and gave me a warm hug and kissed me despite his cum all over my face and inside my mouth. "Of course it is Jenny. If you want me to make you cum while you're tied up like this, we'll go back to that rule, but for now, we're taking a break. I want to know what you want to do now." He then added words that made me shiver with a new anticipation. "If you liked this and we do this again in the future, I'll get a locking collar that will tell you when the game is on and off, which will be when the collar is on and off."

Words gushed out of me too quickly. "Sam I need to cum more than I've ever needed to cum, but I was serious when I said that making you happy is what makes me happy. I want to give you your fantasy tonight. I won't cum tonight. And this... was the hottest thing I've ever experienced. If you don't do this to me again, I'm leaving you!" I quipped.

Sam chuckled and untied me until we were both kneeling on the floor, unrestrained, and we shared the most warm and passionate kisses we'd ever had.

We repeated variations on this over the next couple of months, with me never cumming. He'd asked me again after the second time if I wanted him to make me cum, and I told him to please not ask anymore, as the reality was it was hotter for me knowing during the whole thing that I was not going to be allowed to cum, rather than knowing that as soon as the fantasy was ended I'd have the option. He'd gradually introduced some painful nipple clamps as well as some firm spankings, which I'm ashamed to admit I found extremely hot, something that surprised me greatly. Every session, he told me he'd fuck my ass only when I begged him for it, and every time I couldn't bring myself to do it, as badly as I wanted him inside me that way.

Sam finally brought up the subject of chastity belts. "Jenny if you really want to feel like the choice of cumming is out of your hands, we could get you a chastity belt," he'd said one night. I didn't even think the things existed outside of museums. Sam assured me that they did, and also assured me that while the decision to wear one was mine, it would be a really big turn on for him. "I could deny you for weeks," he'd said. We started talking out the fantasy.

"Would you make me earn my orgasms?" I asked him, something that I'd begun fantasizing about since our little bondage sessions.

"In ways you can't even imagine Jenny," he replied, which brought a moistness between my legs, and, I didn't fail to notice, a hardness to his boxer shorts. "I'll bet I'd have you begging me to fuck your ass in no time," he said in a very, very sexy voice, lust thicker than the air around us. "Are you comfortable enough to let me make up the rules?" I was. I needed him to. I knew Sam well enough to know he would never hurt me or do anything if he could see I didn't want it, and I trusted him absolutely.

We read, researched, measured, and ordered. When our belt came by courier, Sam told me to get undressed, and locked on my collar. I was now used to calling him "Master" when the collar was on, and used to him calling me things like his "little whore" or "little slut", He also used the term "princess" affectionately. He told me to go to the washroom and put on the sluttiest look I could imagine. I overdid my eyes, my blush, and chose a bright shade of red for my lips, and indeed did look like the wanton whore when I was done. Sam hogtied me on the bed, my wrists bound tightly to my ankles, forcing my back up into an arch, my knees forced apart with a spreader bar. He'd bound my torso with the same thick, black leather straps, and put a harness over my breasts and upper back.. He once again approached me, hands behind his back.

"I've got more surprises than just the belt, my little whore," he said, with his huge erection swaying menacingly in front of him. He slowly took his hands out from behind his back and was holding a buckling penis gag. The kind that locked over the top of your head as well as around the side, so it simply could not be spit out. "Open wide, princess," he intoned. I complied and he forced the gag inside me. He then produced a camcorder and set it up on a tripod, looking at me. He then sat on the bed with me, legs apart, my gagged face leaning up against his penis.

"I have rules for you princess," he began. "They are simple, but pay attention now." He was stroking his cock against my cheek, and every once in awhile caressing my bottom. "Rule number one is, your hands will never, never be free when your chastity belt is off. You will NOT be given any chance to relieve yourself". He stroked his cock some more and rolled me onto my side, facing the camera. He began to massage my clit, speaking as I moaned with need.

"Rule number two, is you will always dress and look your sexiest for me when we are at home, barring our having company, and you will beg me to tie you up, tease you, and fuck you at least twice every day or night. This means you will look and act like a little whore every weeknight and every weekend. Any time that you fail to do so, you will be adding one week without an orgasm. I may oblige your begging, I may say no, but you WILL try. If I ever sense that you are going through the motions without putting any effort into your trying, it's a week. Don't forget how much I love you in six inch heels, princess." He had me so close to cumming that I was moaning with need through the gag.

"Rule number three... I know you'll love this one my little slut. You get, at most, one orgasm for every three you give me. After I've cum in each of your mouth, your pussy, and your ass, you will have earned an orgasm. Each night that you beg me to tie you up, tease, and fuck you, you'll have to also beg for where you want me to cum. If I'm feeling generous, I might cum where you asked me to. If I'm dissatisfied with you, I might pull out at the last second and finish off in a different hole. I suspect that most nights, I will simply fuck your mouth and your pussy, regardless of what you're begging for." I couldn't believe how devious he was! There was nothing I could do about it, and I loved every minute of it.

He was again stroking his cock against my cheek. "The last rule is this. The day you first beg me to fuck you in the ass, is the first day that I will be locking the remote controlled vibrating butt plug on to your chastity belt in addition to the remote control vibrating vaginal plug. I couldn't believe what I was hearing! I'd seen those options on the website, but I didn't realize that Sam had ordered them! "After that, you will wear both every time we are home and alone."

I was moaning in frustration. His words and his hands had me ready to explode, but he would not give me that satisfaction. "Don't be sad, my little slut. I've got good news for you ," he said. "Because I've cum in your mouth and pussy so many times over the past two months, I'm giving you a bye on those two to celebrate our new life together.

He was playing with my nipples again and told me to smile for the camera. All I could do was moan with need. He began fingering my pussy and used my juices to lubricate my ass. His finger moved around and around, without penetrating. "Don't worry," he said. "You have to beg." I moaned in frustration and tried with absolute futility to beg around the gag. "What's that, princess? I can't quite make out what you're trying to say" he said as he continued to tease, and tease, and tease.

After an hour of this, I was close to tears, and I felt him unbuckling the gag. As soon as the intruder was out of my mouth, I began begging in earnest. I was past the point of crazy with lust, and I simply could not have stopped myself if I'd wanted to. "Oh Master! Please, please take me in my ass! Please I beg you! I'll do anything Master, just please fuck my ass! I'll be the good slut you deserve Master, please!!" I was sobbing from emotion and the incredible need to cum. I'd been completely broken. I went on and on for fifteen minutes, begging him to fuck me in the ass. The longer it went on without him saying anything, the more afraid of not cumming I became, and the more frantic my begging became.

After another good half hour of my begging to be taken in the ass, he smiled at me, then at the camera, then back at me. "I will my slut," he began, as he rolled me back onto my stomach. "Just not tonight!" And with that he forced my mouth down over his cock and used my mouth for 10 minutes until he came with as much force as I'd ever felt him cum. I shuddered with lust, anticipation, and fear, as he got up and walked over to the courier box, and started attaching the butt plug to the rear shield...

That night was the first time I'd ever had anything in my ass, and I was sorely disappointed that it wasn't his cock. That was over 8 months ago, and to this day, Master makes me put that tape on for him and suck his cock until he cums at least five times a week, while he watches me frantically beg to be fucked in the ass on the television. For my part, you might say I'm over being a prude about anal sex. Master mostly cums in my pussy, and sometimes in my mouth too, but no matter how much I beg for it, I'm lucky if he cums in my ass more than once every few weeks. He'll sometimes fuck me there until he's close, then finish up with his hand all over my breasts or my face. In 8 months, I've cum only 7 times, and true to rule number one, my belt has never been removed unless I've been tied up or under Master's close supervision (as I do need to take care of things at certain times of the month, which Master is very understanding about). While I do realize that ultimately it's because he loves hearing me beg for him to fuck my ass, that it's a real power trip and turn on for him, for me, psychologically, it's now to the point where the best feeling I know is the feeling of his big, hot, hard cock tensing up and spasming inside my ass, and feeling the warmth of his seed as it explodes out of him into me back there.

He's told me that at our one year anniversary of the belt, he's going to change the rules to my needing to be tied up and taken by him and his friend Carl at the same time, in addition to his fucking me in all three places, before I earn an orgasm. I'm apprehensive about it, but Master has agreed at my request that my pussy is sacred and for Master only, so that eases my mind somewhat. I still have almost four months to adjust to the idea anyway. In the end, I just want to please him.

Yours truly,
A happy princess.

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Page last updated 07-Aug-28 by: Altairboy@aol.com