Cuckold from Day One - Part 2



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Please read Part 1 here


Over the course of the next week I watched Emily have sex with each of her current 7 lovers. They were all young athletes at the local university, in various sports. The one thing they all had in common was their cock size. They were all very well endowed. The smallest was Steve, about my length, 8 inches, but was very thick, like a coke can. The largest was Devin, that I met the first day I was cuckolded. His cock was over 10 inches and thick, but not quite as thick as Steve's. The rest fell in the middle, from 8 to 10 inches and various degrees of thickness. They were all healthy, strong, virile young men, that got hard, stayed hard, had incredible sexual stamina and large loads of cum, which I licked up and swallowed after each new orgasm.

One Saturday, Emily scheduled all 7 of her boyfriends to come over and fuck her. Each had 2 hours to fuck her as many times as he could before the next boy was scheduled. She started at 10:00 am and finished at midnight. They all knew each other, and some would come a few minutes early to watch the previous boy finish before his time started. She was fucked almost continuously for 14 hours, with short breaks to go to the bathroom, clean up a little and eat a little. I ate so much cum that day I didn't eat anything else all day. Afterwards, her pussy, ass and throat were all well used and stretched, and she was very sore for several days.

After the last boy left, Emily let me out of my cage for about 10 minutes so that I could jack off, cum on her tits and release my sexual tension. Then she put me back in the cage saying she didn't want to be bothered by my cock for a while. She took a week off from having sex before resuming the regular fucking schedule with her boys and sometimes me.

As Emily was standing in the shower that Saturday night, allowing me to clean her up before bed, I worked up the nerve to ask her how it was that all her boyfriends had cocks that were much larger than average. She informed me that it was no coincidence, that each of them had been carefully selected based on cock size, athletic ability and strength. When I asked how they had been selected, she said she would tell me the next day when she had rested. That Sunday as we recovered, naked in the sunroom, she told me her story. As she told me, she sat on the couch while I laid down with my head resting on her thighs. She would occasionally lower one of her breasts to my mouth so I could suckle it, and she would also tease my cock in its cage. She enjoyed seeing it strain against the unforgiving bars trying to get hard.

Emily's Story:

I don't think Jerry has mentioned before that I am a doctor with a clinic close to a large high school and the local university, both of which are my primary customers. I am the owner of the clinic and the main doctor and have taken primary responsibility for performing all athletic physicals to approve athletic eligibility for the high school and the university, for all female and male athletes. Therefore, I have access to many naked athletic boys and girls, starting in high school and extending through their university athletic careers. But I'm getting ahead of the story. I'll come back to this later.

I should tell you a little about me. I was always a plump girl, from when I first started school. As a result, my breasts began to grow early, at about 11 years old, and continued to grow until they were very large when I started high school, much larger than anyone else in my school. The boys took notice and were always staring at my breasts and making rude comments, even though I dressed modestly. I never showed any cleavage at school, but it was too obvious that I had big breasts. I found later that I could use that to my advantage to date the hotter, athletic boys even though I was not the thin cheerleader type.

During my high school and undergraduate college years, I had a few boyfriends and girlfriends and took advantage of the freedom I had during those years to experiment with my sexuality with a variety of partners. I started on birth control while still in high school when I started having sex. Girls seemed to like my big breasts as much as the boys did and I loved playing with girls almost as much as I enjoyed fucking and sucking cock.

One particular boyfriend that I had during my junior year (Brad) proved to be a little different than all the others. He was a senior and we had dated a couple of times when at the end of our date I invited him up to my apartment for sex. He readily agreed and as soon as we closed the door we started kissing and taking each other's clothes off. When he unhooked by bra, the girls tumbled out, to his delight. He buried his face between them and used them to slap himself on the face. I was enjoying the attention, but also wanted to get his pants off.

When I finally pulled Brad's pants and underwear down, by hooking by fingers on either side of him and pulling both off at the same time, the surprise was truly mine. A large hard cock sprang up and hit me in the face. It was far larger than any cock I had ever felt before. I was not interested in porn, so I had never even seen anything like it. I tried to take it into my mouth but could barely fit the head inside. When he pushed a couple more inches in, I began to gag. I sucked on the head and even with both hands on his cock, there were several inches uncovered.

I pulled Brad into the bedroom where he pushed me back onto the bed and spread my legs wide. He lowered himself down and started licking my pussy with gusto. I was enjoying myself but knew I wanted more. I tried to pull him up and when he realized how wet I already was, raised up and placed that monster at the entrance to my pussy. That first time that he entered me, I thought he was going to split me in two. He went slow and pumped back and forth, going a little deeper with each thrust. It took several minutes to inch his cock in. The entire time I was screaming with pain, but also somehow, pleasure. I finally felt his body bump up against me and knew he was all the way in.

Brad stayed there for a few minutes as we kissed and he played with my tits, so that I could get used to his size. He then started to slowly pump, pulling out a little further each time but always thrusting all the way back in. It was then that I realized that he was hitting places in my pussy that had never been touched before and the pleasure of having these new places stimulated soon started to overcome the pain of being stretched so wide. He continued to pump, faster and faster, pulling almost all the way out then thrusting all the way back in. The sensations were indescribable. I had no idea that sex could be that enjoyable. He pumped for several minutes, fast and hard, until I felt a tingling building inside me. The feelings grew until I stiffened and came with the most intense orgasm I had ever experienced. As part of my orgasm, I gushed juices all over and around his cock.

He stopped pumping and held me close while I shuddered in orgasm. When I had recovered, he said “You never told me you could squirt.” I told him that I didn't know what that meant but that I had never had an orgasm that intense before. He started pumping again and soon was thrusting in and out as fast as he could. The hard pumping caused my tits to jiggle and sway with each thrust. Brad seemed entranced by this and couldn't take his eyes off my bouncing tits. He finally screamed that he was cumming and where did I want it. I threatened him with his life if he were to take his cock out of me, so he came inside me with a power I was unaccustomed to. I felt his cock twitch and felt the cum being pumped deep inside my womb. I didn't let him take his cock out of my pussy until he had fucked me again, slow and easy this time, and deposited another huge load inside me.

Brad and I fucked a couple more times that night and again in the morning until we had to stop, get dressed and go to class. He even made me squirt a couple more times. We fucked regularly the rest of that year and even worked on my blow jobs so that I could eventually take him down my throat. We never had expectations of a long-term relationship, however, since we had little in common other than the mind-blowing sex. So, I was not crushed when he graduated and moved away but knew that he had ruined me for normal sized men. I knew that size really did matter to me.

I met my husband in medical school where we both were interns. We had lots in common and fell madly in love with each other. The sex was even pretty good, though he was only slightly larger than average, maybe seven inches. We tried to have kids right away but were not successful. After several tests it was revealed that I had a growth that was preventing me from getting pregnant. I had to undergo a serious surgery that rendered me unable to ever have children. This was a severe blow to both of us as we had wanted a family. We discussed adoption, but my husband was not interested in that avenue.

From the beginning my husband and I were active in the swinging community and had several threesomes, both with other men and other women. One of the pictures below shows me fucking another man when I was on the chubby side but still not as plump as I got a few years later.

When we finished our medical training, we opened the clinic next to the schools and started the business of athletic physicals. He would do the males and I would do the females. I always made the girls do the exam completely naked and examined them everywhere. I would also question them as to whether they were sexually active and if they were, I got them on birth control right away, even if they were underage. I also successfully seduced a few of the college girls and often had sex with them during the exams. Everyone in the office was in on it, so no one bothered us. I even shared a couple of them with my husband.

Things went on like this for a few years until one day my husband served me with divorce papers and told me he had fallen in love with our pert little nurse that he had gotten pregnant. I was totally devastated, and the stress caused me to lose some weight. I started taking care of myself, eating better and working out. I eventually lost 75 pounds. I lost the weight almost everywhere on my body including my breasts. I lost some of the fullness in my breasts that I had had when I was plumper. My breasts, which had been very large naturally sagged, but the lost weight caused the sagging to be even more apparent. This caused me a lot of concern and I even considered some plastic surgery to remedy the issue, but soon found that the men and women I had sex with seemed to like them just as much or more than before. I found myself much thinner and more fit but with somewhat deflated, saggy, floppy tits. They did still have plenty of volume and when packed into a bra stood out and displayed a great cleavage.

I got the business in the divorce and soon was doing all the male physicals also. I continued the practice of requiring all patients to be naked for the exams. For the boys, even the small to medium sized ones, I required that they get hard for me, jack off and give me a sperm sample. With some of them I had to take my tits out and let them play with them in order to get them to perform and cum. My explanation was that I needed to check out their reproductive organs to make sure everything was working right. I also told them that, especially for elite athletes, it was important to have lots of testosterone and that it was ok for them to be having sex or jacking off regularly, but never for a couple of days or more before a game. I explained that the sexual tension would improve their performance. I'm not sure if that is true, but they all seemed to buy it and while I never fucked any of them before a game, I was often visited for a strenuous fucking after a game, especially if they had won.

A side benefit of performing the exams was that, on a rare occasion, I would find one of these athletes with a large cock. I sometimes found them when they were only about 14 years old but could tell that they would be well endowed by the time they left high school. For my favorites, those with the large cocks, I even joined them in being naked for the exams. I showed them my body and instructed them on how to please a woman in various ways. I even lined some of them up with my favorite girlfriends and made sure they told me all about the sex they were having.

I seduced the college boys right away and was always successful in getting them in my bed. When the high school boys turned 18, I also started fucking them. In a few years, my little club of well-endowed boys had grown to about 10 members, pun intended. Some of the boys I found turned out to be arrogant, misogynistic and, therefore, not good lovers. I soon dropped such boys from the group. The ones I would keep were humble, caring and generous lovers, even though many were well known sports stars. I would teach them how to please a woman and they were quick learners. I would let them cum inside me uncovered, fuck my ass and stick their cocks down my throat, all things that their cheerleader and sorority girlfriends would not allow them to do. In return, they would do everything they could to please me. The boys I ended up with in my club were young energetic lovers, eager to please and seemingly insatiable.

Some years I might add two boys to the club, some years, none. As they got older some went on to star in professional sports, others got married or graduated and moved away. Lucky for me that there seemed to be a constant supply coming up of just what I wanted – young athletic boys with large cocks. The size of my club generally ranged between 5 and 8 young studs.

Through experimentation I finally determined a minimum size for me to be interested was 8 inches, but at that length I required a girth that would stretch me out and fill me up. The largest, like Devin were in excess of 10 or 11 inches and thick enough to spread me wide while stimulating those special places deep inside my pussy at the same time. Most were somewhere in between. Many of these boys were larger and thicker than Brad, my college boyfriend. I also ended up establishing a maximum age of 24, for those that stayed around, just so my club would not get too big and to give opportunities for the younger guys.

I did notice that although I was having fantastic sex on a regular basis, I missed the companionship of a more mature man. When I saw Jerry's profile on AFF, I was intrigued, not only by his cock size, but by his willingness to share his partner with other men. I read and studied extensively about the cuckold lifestyle and decided that if I did meet a mature man to share my life with, I wanted to keep him in chastity, at least some of the time. That's when I came up with my rules, bought a cock cage, met him and took him back to my place to test him with a couple of my boys. He passed those tests easily and soon we were inseparable.


The telling of Emily's story had taken all afternoon since I had many questions and pressed her for many details that I don't have room to include here. The whole time she had been teasing me by playing with my cock in the cage and by letting me taste her tits. The pain of straining against the cage was driving me insane, especially during the sexy parts of her story. I begged her to take me out and jack me off, or at least let me jack off to ease the pressure. She giggled at my begging and continued to tease me mercilessly. Then she seemed to get an idea. She wondered out loud if it would be possible to make me cum while still in the cage. My heart sunk at hearing this as I then knew that I would not be getting out of the cage that day.

With that thought Emily upped her teasing to a new level. She focused on the head and the sensitive spot she often stimulated when she wanted me to cum. In spite of the increased, severe pain, or perhaps because of it, I soon exploded in orgasm and sprayed cum into her hand. She had me lick it all off her hand and fingers while my cock relaxed back into the cage and the pain subsided.

Emily seemed very contented with herself that she had succeeded in making me cum while still in the cage. Again, I heard her ruminate out loud about embarking on some serious cuckold training. Little did I know at the time that my experience with various types of cages and even more severe pain was only just beginning.

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