Part 1 - The Beginning
My story is a little different from most I have read on here. In my mid 50's I found myself newly single due to my wife's protracted fight with cancer. The sex life with my late wife of over 30 years had been satisfying, but very vanilla, and non-existent for the last year of her life. I had been reading, and masturbating, to cuckold stories, pictures and videos for many years, but never brought up my fantasy with my wife.
With her gone, I joined AFF. In my profile, I explained that I was looking for a travel buddy, with benefits, as I wanted to start exploring the world again, but didn't want to go alone, and that I would cover all travel expenses. I went into some detail about my sexual experience and fantasies and included some pictures of myself, including of my cock, which is a thick 8 inches. At the end of the profile, I mentioned, kind of an aside, that I did not require exclusivity because I also had some cuckold fantasies.
I had limited success with my profile and met a few women around my age that I went out with. I even ended up fucking a couple of them, but nothing really clicked with any of them after a while. I also met with a couple for a threesome, which was amazing and my first time with an extra person there. They were older than me, but she still had a hot body and nice natural tits. I enjoyed being watched by the husband as his wife sucked my cock then spread her legs for me to enter her.
She didn't want me to cum inside her so, when I was close, I pulled out and came all over her beautiful tits. I looked into her eyes and asked if it was ok if I licked up the cum from her tits. (One of the fantasies I had talked about in the profile was to eat cum and had been eating my own for a while to get used to the taste and texture.) She readily agreed and I dove in to lick all the cum off her nipples and tits.
While I was at it, I felt him enter her and start pumping, which caused her tits to bounce around beautifully. When I had all the cum cleaned up, she grabbed my face and pulled me into a deep kiss, where we shared my cum. After a while, I heard him moan as he filled her pussy with his cum. When he pulled out, she broke off our kiss, spread her legs and pushed my head down between them. It was my fantasy fulfilled. His cum was oozing out of her pussy and running down the crack of her ass. I pushed her legs up and out to open her up and started licking at her ass hole to get all of his cum. Then I moved up to her pussy and licked and sucked until she came with a scream and a gush of her fluids with the rest of his cum. I was in heaven. I met with them just a few times and then she let me know that her husband was getting jealous, so she had to cut it off. It was a very depressing development.
Around that time, I got a message from a woman on AFF saying that she would be interested in meeting me. I recognized the profile name since I had browsed through all the female profiles in my area several times. She lived about 5 minutes away from my place.
What surprised me was that she was much younger than me, late 30s, and in her profile, she expressed an interest only in young men 18-24 years old. She had no pictures on her profile, but described herself as a fit, curvy woman, with large, saggy breasts, that looked a little younger than her age. That sounded great to me.
She introduced herself as Emily and we set up a meeting for the next weekend, but in the meantime continued to chat online about our fantasies and what we wanted out of a cuckold relationship. I made clear to her that it was all new to me but that I had thought about helping my cuckoldress prepare for her dates by helping her bathe, shave her legs and pussy, get dressed, prepare the atmosphere for the date and clean up the cum from her pussy, or wherever else the guys would cum. She mentioned that she currently had 7 young men, the youngest 18, the oldest 22, that she was having regular sex with but wanted a long-term relationship with a mature man that didn't mind her fucking the young men, usually every day. My mention of being a cuckold attracted her attention. She even sent me a few pictures that showed her large, full, pendulous breasts on a soft, curvy body.
We met for lunch on Saturday at a fast food restaurant to get to know each other. I got in Emily's car when she arrived, and we went through the drive-through before parking in a remote corner of the parking lot for privacy. She was wearing a low cut blouse with a push-up bra that created a beautiful cleavage that I had a hard time not staring at. As we talked, I felt her taking control of the situation. She told me that if we were to continue, I would be expected to follow a few specific and uncompromising rules.
If I couldn't abide by them there would be no reason to continue. She then told me:
Rule #1: I was to be submissive and completely obedient to her in all sexual situations.
As soon as I agreed, she instructed me to remove my pants, which I did without hesitation. I was surprised at the influence she had on me already. She reached over and started to play with my cock, which immediately hardened to full size. As she slowly pumped on it, she smiled and told me that she was happy I hadn't lied about my age or cock size on my profile, that it would have been a deal breaker. Our relationship, she said, had to be based on honesty and trust.
Emily said that for her young boys to allow me to be in attendance when they fucked, we had to create the illusion that I was not allowed to have sex with her. To do this she informed me of:
Rule #2: My cock had to be in a cage whenever I was with her and her young boyfriends.
She then reached into her purse and pulled out a shiny metal object, handed it to me and told me to put it on. I had never seen a cock cage before, so she had to show me how it worked. The problem was that I could never get it on with an erection. Emily reached over and flipped the head of my cock hard with her finger. It hurt like hell and my erection quickly subsided. I slipped the cage on and she locked it up with a small padlock. She then told me that she was meeting one of her boyfriends in a couple of hours so we needed to hurry back to her place so I could help her get ready.
We went straight to Emily's place and as soon as we entered, she informed me of:
Rule #3: Whenever I am with her and not in public, I must be completely naked.
She indicated that I could leave my clothes in a small coat closet next to the door. I immediately stopped and stripped my clothes off as I saw her continue down the hall. I quickly followed her into what I could see was her master suite. By the time I got there she was down to her underwear. She turned and faced me as she removed her bra, and her massive tits tumbled out. When she bent over to remove her panties, they hung down and swayed back and forth. I couldn't take my eyes off them and my cock immediately tried to harden. As it did, the pain became excruciating as the stainless-steel cage was completely un-moveable. I saw her smiling at me when she saw the expression of pain on my face. She took my hand and led me to the shower.
As Emily stood in the center of the shower, I cleaned her from head to foot, including washing her hair and soaping her totally over her entire body. She had me focus on the underside of her large breasts, as she said it is an area that sweats a lot. I loved soaping up and massaging her big, hanging breasts. She also had me clean deep inside her pussy and ass by inserting a long soft soapy brush as far up as it would reach then rinsing with the hand-held shower head. She mentioned that she had given herself an enema earlier because she knew we wouldn't have time but that I would be responsible for helping with that in the future.
During the entire process, my cock was straining against the unforgiving cage, causing me extreme pain. She seemed to get a kick out of that. When she was sufficiently clean, she sat on the small bench in the shower as I shaved both legs until all stubble was gone and then her private areas until her pussy and ass were silky smooth. We left the shower and I dried her off completely and she sat on a small stool to do her hair and makeup. She mentioned that I would receive training on those areas if I stayed around. As she worked, she opened her legs and told me I could eat her pussy.
I knelt between her legs and started licking and sucking. I used my tongue to flick around her pussy then focus on her clit. She seemed to like that and spread her legs wider. I also licked between her lips, spreading them, then tried to stick my tongue inside her as far as I could. Then I would go back to flicking. It seemed to be working as I heard her start breathing harder and could feel and taste the wetness from her pussy. However, when her hair and makeup were done, she stood and said that I would have to work on my pussy eating technique if I wanted to stay around and that she hoped I would be equally enthusiastic about eating her pussy when it was covered and filled with cum.
She took me by the hand again and led me to a chair in the corner of her bedroom and informed me of:
Rule #4: Whenever she is with one of her lovers, I am to maintain complete silence, never speaking even when being spoken to or about, and will respond to any instruction of hers immediately and to the best of my ability.
As the last rule was sinking into my consciousness, I heard a soft knocking at her door. She looked at me and said the next few hours would determine whether I would continue as her cuckold or not.
The boy that followed her through the bedroom door (Mark) was young, 18 or 19, at least 6 foot 3 inches tall, very well developed and with a large hard cock that she had a hold of, leading him along. She motioned to me and said, "This is the cuckold I told you about but don't worry because he won't bother us or leave the chair unless it is to clean up your cum".
He smirked at me, turned away and they both continued as if I didn't exist. They kissed passionately while their hands explored each other's body. She dropped to her knees and took him into her mouth. I was surprised when she opened wide and took his entire 10 inches into her mouth and down her throat. She alternated sucking on Mark, licking the head of his cock, sucking on his balls and deep throating him for several minutes. When he started getting close to cumming he held her head in his hands, forced his huge cock down her throat and pumped violently for a couple of minutes. As he started to cum, he pulled most of the way out so she could suck on him and get all his cum in her mouth. I saw her motion to me to join her, so I dropped to my knees next to her and opened my mouth.
She positioned herself above me and let his cum ooze out of her mouth onto my tongue. I couldn't believe how much there was, it seemed to just keep coming. At the end I closed my mouth and swallowed it all. She smiled at me and motioned me back to the chair. By the time I returned and sat on the chair, he had laid her on the bed, spread her legs wide and was inserting his hard cock into her. He had not even gotten soft.
I'm not sure how long Mark stayed that afternoon. It seemed like hours. They fucked in a variety of positions, her on top, doggy style, athletic yoga type positions, and in all of her holes. In addition to the first blowjob cum, I licked his cum from her ass, her pussy (twice), and finally from her chest and between her tits as he finished with her soft tits wrapped around his cock. In between fucking they would cuddle and kiss and talk. He also sucked and played with her tits and told her all about the baseball game he was in earlier that day. When he finally said he had to go, she walked him out.
When Emily returned, she told me I had done really well and that she would like to take me out of the cage and fuck me, but that Devin was coming in just a few minutes. She said he liked to fuck her after she had been with another guy that had stretched her out a little. When Devin arrived, I saw that he was a young black student about 21. I recognized him as a player on the local university basketball team. He was taller than Mark, equally as handsome and developed but his cock was huge. It was about the same length as Mark's, but much thicker. When Devin tried pushing it down her throat, she couldn't quite take it. As before, over the next few hours, I licked cum from all her holes and off her body as he came with large loads many times.
I watched in awe and tried not to think of the pain caused by the steel cage enveloping my manhood.
When he left, Emily came to me and removed the cage. She praised me for my performance and obedience and led me to the bed. She laid on the edge and spread her legs so that I could slide my cock into her pussy. It was well stretched out and slimy inside from the multiple cum shots deep into her pussy over the last few hours. It felt like heaven to me as I slid in effortlessly. I tried to last a long time but was so aroused and frustrated from the previous hours of watching her get fucked mercilessly, that I came in only a few minutes. I promptly dropped to my knees and licked it up as it oozed out of her well used pussy. I continued to lick and suck, with some instructions from her on just how she liked it, until she orgasmed and squirted all over my face.
When we had both recovered, she allowed me to fuck her equally stretched out ass before she led me back to the shower. (The next morning, she gave me the most incredible blow job I had ever even fantasized about, completing my initiation). Once again, she stood in the shower as I cleaned her completely, from head to foot, inside and out. We then cuddled under the blankets on her bed. The last thing I remember before I drifted off to sleep was her saying, "I think I am going to enjoy having you around."
So began our cuckold adventure. I have stories of many sexy and interesting experiences that we have shared. It all began when she made me her cuckold on the very first day we met.
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