Cuckold in Training

When I saw her I was attracted to her. We were both taking part in a work activity and she was popular as a lot of men were trying to talk to her. I watched her as she rebutted their advances but it was her easy manner when doing so made her very appealing. As the day wore on we ended up being paired together. We worked well together and she spent more time with me later on. "Would you like to have a drink sometime," I blurted out when it came to part. She replied asking if the next day would suit.

We met up for our date and it was a very enjoyable evening. We both had a lot in common, had shared or common experiences to relate to each other and we both kept each other entertained. As we left the restaurant I leaned in to kiss her but she put a finger up against my lips and said, "meet me tomorrow at mine and we'll continue this there."

The time couldn't pass quickly enough and I spent the day clock watching and rushed round to hers at the required time. She led me inside and made me sit down. She sat on the floor at my feet and took my hand. I wondered what was coming as she couldn't dump me from a relationship which hadn't even begun and she could have let me down over the phone. "I like you," is how she started. I sensed a but coming but she continued. "We are both very similar in terms of our intelligence and emotional maturity and I know you are attracted to me like I am to you but in different ways," she continued to say. She went on to finish with, "I wonder if you'd like to be my Cuckold?"

I was quite shocked. I vaguely knew what a Cuckold was and guessed they must exist but I had never met one or thought of being one. She continued with, "I can't be monogamous and need other men to satisfy me sexually but need a man like you for the day to day stuff." I think she could sense that it was a lot for me to take in and so she continued talking. "However, if you do take this role on there are a number of rules you will have to obey." She then went on to explain more.

The first was sissification. She expected her Cuckold to transition into a female role when in her presence by wearing female underwear, clothing, make-up, a wig and remove all body hair. She had picked me as I have features which would make me look convincing as a woman such as not too large hands, a lack of five o'clock shadow and a slim athletic figure. "You have legs a lot of women would kill for so let's show them off and showcase them in stockings and heels." My wardrobe would be selected by her and would feature a range of subservient apparel, notably a maid's outfit to show my place.

Next was enforced chastity. She would make me wear a lockable steel cage around my cock and balls. She had found that Cuckold's are dishonest when it comes to abstaining from sex and that chastity was the only way to curb this. I would wear the steel cage at all times except when she would allow me to take it off to masturbate. "You need to be prepared to go three, maybe even four weeks at a time between the occasions where I will allow you your own pleasure." All access to pornography was also to be prevented and I was only to use electronic devices she provided me which had an adult filter applied.

Being able to have that sexual release came at a price though as the next requirement was to learn to eat cum. "We'll start with your own cum, and then we'll move you onto eating other men's cum after you have sucked their cock." Sucking other men's cocks would be a requirement whether they were men who would later penetrate her or other men who she felt just needed their cock sucking by a man to prove their worthlessness. "I know women who love to see their husbands submitting to another man's mouth." She would allow me to shoot my load onto her leather boots or leather clad bottom but I would have to lick it all up afterwards. Other men's cum would have to be cleaned out of her pussy. She liked to let it flow out and for her Cuckold to lick the remainder by pushing his tongue deep inside her tasting both her own juices mixed with her bull's. I had to give up any idea that I would be allowed to penetrate her.

She moved her hand up to my crotch and felt me hardening through my trousers. I have to admit that so far she had mentioned a number of trigger words that I use to search for porn and so I was getting erect. "See, you're warming to the idea," she said and unbuttoned my trousers allowing my restrained cock to spring free. She started to wank it and continued.

"I like my Cuckold's to be silent," was the next requirement. She hated hearing a submissive say, " yes mistress," or, "no mistress," cry or complain and so insisted on a vow of silence at all times. She reiterated that complaints would not be tolerated.

All of the above were to be carried out to her instructions otherwise she would punish her slaves. "I tried all sorts of things but physical punishment is the best." She likes to use a riding crop to begin with and the gradually work up to the rattan cane or carpet beater. "The cane is so brutal, it marks so easily and shows who's boss." She also liked spanking and face slapping.

Those were her rules and they were non-negotiable. To help with this arrangement she had drawn up a Dominant/submissive contract to help put them in place and passed it to me with her free hand. As I read it she looked at me and said, "I think we both know it is what you want." As she explained this requirement I could feel my climax coming and told her. "Good little cuckold, you're learning my ways, and as it's your first time you may come without needing to seek permission." Just then I climaxed and cream erupted from the head of my cock and covered her stimulating hand.

I finished with, "where do I sign?"