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How it began
08/12/2013
I am getting older and have been thinking a lot about how it is that I ended up as a cuckold. It really started 30 years ago when I was still a teenager.

I had already lost my virginity to a horny little girl that I dated for about a year. She liked to fuck and I got used to having my way with her pretty much whenever I pleased. Looking back on it now, I think that made me more than a little arrogant. I thought I was the king and could have my way with any woman I wanted to.

She dumped me for another guy, which was quite a blow to my ego, so I began chasing women and actually had a lot of success. I would lie to them, telling them whatever I thought they wanted to hear just so they would let me fuck them. Usually it didn't last more longer than one or two encounters before I (and I'm sure they) were on to the next one.

Then I fell for a real beauty named Michelle. She was different in that she wouldn't just let me do her. I had to work for it for months. We went to movies and to dinner and spent time studying together. She would let me make out with her, but it took a long time before she didn't push my hand away when I began rubbing her tits, and it was another month or two before she let me rub her pussy through her jeans. I can't count how many nights I went home with a raging hard on and jacked off in bed thinking about her.

One day she asked me about that. She said, "Do you masturbate?" I said, "Um, yes, of course I do."

"How often?"

"Almost every day," I lied. It was every day, and often twice a day.

"That is not good for you. Did you know that it's bad for you to masturbate? It will make the real thing less pleasurable."

"Well, I wouldn't know that, now would I?" I said, maybe a little sulkily.

"No, I suppose you wouldn't, at least not with me. But don't you want to find out?" she asked.

Of course my cock was hard by now. "You know I do, honey."

"Here's the deal: I want to have sex with you, and I've decided I will, but I'm not going to until you go at least a month without masturbating." She was smiling this amazingly seductive smile as she said this.

"A month!? There's no way I can go a month!!" I almost yelled.

"Suit yourself. I guess you need to find another girl then." Then she leaned over and gave me a deep french kiss as she rubbed her hand slowly over my crotch for the very first time.

Of course I was lost at this point. I made up my mind to not masturbate for a month if it killed me. Michelle let me slide my hand up under her shirt and bra. Her nipples were rock hard. She was grinding her pussy against my other hand, but stopped me when I began fumbling to undo her jeans.

"Ah ah ah!" she wagged her finger at me as she pulled away. "All in good time. First you have to control yourself for a month."

I wish I could tell you that I made it a whole month from that night, but of course I slipped up, first after about a week, and again after I had made it over two weeks. Shit, I was 19 years old - looking back I don't know how I made it that long, other than to say that she was smoking hot, with dark hair, brown eyes, and a brilliant smile. Her body was hard since she was a swimmer like me, and she has a very outgoing, attractive personality.

Somehow she always knew when I had masturbated and reset the clock. She didn't make it easy, either, seemingly taking delight in getting me worked up every time we were together. She kept telling me how it was necessary for all my desire to be directed toward her. She had learned that from her mother and grandmother, she said, and their marriages had lasted decades. That's what she wanted, and she was going to make sure she followed their example.

After failing four times to make it 30 days, finally I was at day 29 and knew that I could wait another day for the prize. It was a Friday, and I had already saved my money so I could rent a hotel room and fuck her nice and slow Saturday night after taking her to dinner.

I saw Michelle at school during the day, as usual. She was beaming bright. Between the last two classes of the day she caught me in the hall by my locker and whispered, "Only one more day, young man. Do you think you can make it?" as she furtively brushed her hand up against my bulging jeans. I groaned and she giggled as she walked away - actually, she was almost dancing, it seemed.

I saw her briefly at the football game that night, but she had already planned to go out with her girlfriends, and some of my buddies and I got together and got drunk on beer. It was better that way, I figured - no sense in taking a chance of blowing it the last day. I was so horny I could barely stand it.

The minutes crawled the next morning and afternoon as I waited for the time to come when I could get in the car and go pick her up. I busied myself with yard chores. Dad seemed amused by my energy. "Big date tonight?" he asked.

"Yeah - well, no, still Michelle, nothing new, but I have to admit I'm looking forward to it," I mumbled. I wondered how much he knew. He could read my mind sometimes.

Finally the time arrived. I scrubbed well before dressing, sweating every detail of my clothes and appearance, wanting to do everything I could to turn her on. When Michelle came downstairs as I waited in the foyer with her mom, I let out a little gasp. She was stunning! Her smile was bright, and her mom gave me a little wink as we turned to go.

I babbled for a while at dinner, then listened intently to everything she said as she talked about her friends and the events at school and all the things going on with her family. My loins ached with desire.

After dessert, she looked me right in the eye and said, "Are you ready to fuck me?"

I was shocked at her use of the word 'fuck.' It was the first time I had heard her say that word, since although she would smoke weed and drink occasionally, she was otherwise very proper and didn't use foul language. "Yes-ss, yes, I am," I stammered.

"Good," she smiled. I took her by the hand and led her to the car. We drove to the hotel in silence - I had already paid for the room, gotten the key, and made sure it was clean and inviting before I picked her up.

When we got inside, she walked in to the room and inspected it quickly as I locked the door. She turned to me and said, "Take off your clothes." Just like that.

I was a little taken aback, since I had planned to be the aggressor as I had always been with other girls. I started toward her confidently, but she stopped me cold with a steely tone of voice. "TAKE OFF YOUR CLOTHES NOW OR I WILL NOT FUCK YOU."

I stopped, a little disoriented, then giggled nervously and began to undress. What the fuck, I said to myself, as long as I finally get inside of her.

I was completely naked in no time flat and again began to advance on her, my erect cock leading the way. "STAND STILL!" she said, again with the steely tone. "You are going to learn to do as I say, or this is not going to work and you are going to go home without fucking me. Do you understand me?"

I said, "Whatever, sure," a little pissed at her attitude.

"No, it's not 'whatever, sure' - not if you want to fuck me. It's 'yes honey' or better yet, 'yes, ma'am' from here on out. Got it?"

I was reeling now. I really hadn't expected this. I debated whether to say fuck it to the whole thing and find another girl. This one was apparently crazy. But I said, "Yes, ma'am" with just a tinge of sarcasm in my voice.

"That's better," she said. "Now lay on the bed."

I pulled the covers back and lay on the bed, my cock jerking in the air by itself. She stared at it for a moment, then reached in her purse and pulled out a piece of cloth.

"Do you trust me?" she asked. "Do you trust that my mom and grandma have taught me how to make sex something really special?"

"Sure," I said.

She slapped the head of my cock hard with the palm of her hand. I winced, bouncing on the bed as I curled up from the blow. "What the fuck!" I yelled, trying to get up.

"Say, 'YES, MA'AM'!!"

I fumed. "Yes, ma'am," I finally said, the pain and surprise subsiding. This chick is definitely crazy, I thought to myself. But she was so fucking hot that I calmed myself down.

She leaned over me, letting the silky soft shirt covering her breasts brush against my exposed erection as she wrapped the cloth around my head, covering my eyes. I bucked a little, trying to rub against her, but she just pushed me back down by pressing her hand against my belly firmly. It felt so good!

I heard her fumbling in her purse again, then felt her pull my hand toward the corner of the bed as she slipped a rope over one wrist, then the other. She tightened it so that both my arms were above my head, not uncomfortably, but securely.

"Pull on it," she said. "It's very important that you cannot get loose, so pull on it as hard as you can."

I did, and to my surprise she really had secured my hands to the top of the bed somehow. I struggled a little harder when I realized how vulnerable I was, unsuccessfully, which made her giggle.

"Have you ever been tied up before?" she asked. "Did any of your nasty sluts ever tie you up like this?"

"N-no. What do you mean, 'my nasty sluts'?" I thought I had carefully concealed my past sexual escapades - certainly I had never talked to Michelle about them.

"I know all about them, you fucker. Girls talk. Didn't you know that?"

I tossed and turned a bit with that revelation. I could hear her clothes dropping to the floor as I lay there in the darkness of the blindfold.

"You have to be all mine, or it's not going to work. Do you understand that? You've been with other girls, so I have to know that you're not going to stray if I start fucking you. I want a man who will be loyal and faithful, or I will walk away. Are you that man?"

She was laying on the bed next to me now, whispering this in my ear. Her leg brushed against mine. Her nipple tickled my side, then her breast pressed in against my chest. Her hand brushed against my belly, sliding slowly toward my cock.

"Yes, yes, I'm that man! I only want you, baby!" I moaned. Despite feeling powerless and humiliated by my circumstances, I had never been so turned on in my life.

"Good. Do you understand that being mine means that I am the only one who has the right to give you orgasms?"

"Yes, yes honey!" I shivered. "I haven't masturbated for a month! God, please, please honey!"

"Please what?" she whispered as she licked my ear.

"Please let me fuck you!" Suddenly she squeezed my balls, hard enough that I bucked up in surprise. "I mean, please ma'am!!"

She kissed me full on the mouth, then slid her tongue into my mouth as she circled her fingers around the base of my cock and squeezed. She shook it back and forth, never touching the head. I thought I would pass out.

Next I felt something tightening around my cock, something soft, like cloth. She sat up and tugged it tight, tying a knot under my balls. Then she did the same to my balls, tying them off so tight that they ached.

"I don't want you to come too early. It's been a long time, hasn't it? You might just decide to let loose, and I can't have that."


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