The beginnings: Jeff - CuckoldPlace.com

This is the first part in a series of three parts that chronicle the cuckold experience I have had spanning over a decade. I never knew that there was such a term to describe what I soon learned to enjoy until I found an online free erotic story site (Literotica) and some of the stories mentioned the term cuckold; since then I have found this site and have fed my addiction to the cuckold ideology.

My wife Holly and I back in the early 1990's got married after my return from the Persian Gulf War; one of my closest friends "Jeff" who lived at home with his lady, sister Jeanine and her husband Jerry would often have us over to play cards and take. His sister was an attractive blonde haired woman and would often talk about sexual topics during our evenings at their place. Jeff was not impressed with his siblings swinging stories and her tales of using various vegetables for self pleasure. I secretly visualized these things and actually had hoped to be a part of their dirty lifestyle. Shortly after our wedding Holly; a brown haired, brown eyed girl that was still fit from years of inter-league swimming standing at 5' 4" and having rather shapely legs and a 36c chest began to speak more openly of the misadventures of Jeff's sister and husband.

Holly was a sexual dynamo that loved sex and we were engaged in sex on a regular basis; she loved to watch porn, experimented with sexual toys and loved to wear lingerie and stockings for my pleasure. She mentioned one evening while watch a double penetration video that she at times feels that she will have missed something by marrying me and not being with other men before getting married. I was curious, she asked me if I felt the same way by being a virgin as well before we met; I had no complaints. I tried to duplicate the scenes on the video and she would get hot if a dildo was in her ass while I drove my cock into her wet and hot pussy and spoke as if there was another guy doing her ass. Holly got very hot at this idea of having "somebody else" fucking her ass at the same time. This led me to pry her into admitting that "Jeff" was cute and she thought that he would be acceptable to have sex with. After thinking about this and how I got hard hearing this from her and running through my own mind what might happen I agreed to let her try to seduce him.

Holly began to visit his house using his sister Jeanine as a reamister why she was there; Jeanine figured out right away why Holly was there and I was at home because of a long and tiring day at work (yea right). Holly got Jeff to go out to eat and then began to work on him. The rules I laid out were simple...she could do anything he was willing to do as long as she came home at a reamisterable hour and allowed me to have my way with her when she returned as she described what happened. They met three times and this is how it went for her.

The first time out they ate dinner out and she was worried about his sister and lady possibly saying something so she made a move in the car. Jeff was freaked out at first and she talked him into trying to understand that she wanted to seduce him for the purpose of pure natural lust, not a relationship. He caved in and she undid his pants and began to work over his enlarging cock that she described as being similar in width and about an inch longer than my own 6" cock. She began to alternate between a hand job and a blow job; that is her trademark move. Jeff undid her shirt and played with her tits, never removing her bra and just slid his hands over the satiny smooth material and kneaded her nipples between his finger and thumb. They were like this for a few minutes until she jerked him off and cum flowed out and spurted unto his abdomen; she does not like cum in her mouth, pre cum she will willingly lick up and play with...no cumming in her mouth except for a couple rare times. Holly rushed home and crawled into bed and laid a big wet kiss on my mouth and I could taste his cock on her lips and it was great! She was so wet and hot as she impaled herself on me and rode me hard into a great orgasm for both of us...at the time we practiced the "timing" method and she jumped of me after cumming and jerked my sticky, wet cock into a great cum as cum spurted into small pools all over my belly and chest. She was disappointed that it did not get far; so was I since I had anticipated a wet loose cunt to clean and fuck.

The second encounter they met for dinner again and this time his lady was out for the evening and they went into his room not knowing that his sister was going to listen to the entire evenings events. Holly undid his jeans and pulled them down and then his boxers and began to suck his cock in earnest since she was hoping he would fuck that night. Instead he only fingered her pussy and ate her for a short time. Holly sucked and jerked his cock off again and came right home to me where I went down on her wet and hot pussy and noticed that it was not very loose and she told me what took place just before I again fucked her hot hole...this was still the best sex ever because she was thinking of him the whole time and what he might do with his larger cock. I licked and sucked the cock taste out of her mouth and she asked if I liked tasting his cock and I openly admitted that I did and wanted more. So that night she sucked me off and would go between kissing me and my dick and again I exploded a great glob of cum all over my self.

A few days went by and Jeff called and told holly that his sister was giving him a difficult time because she heard everything and got herself off in the hallway; thus he was nervous about doing anything at home and decided to get a hotel room. Holly wore stay up thigh high stockings (black, how slutty) and went off to see him again. This time he was eating her pussy for all he was worth and in a 69 position pulled out of her mouth and came all over her tits. Jeff rolled off of her and watched Holly smear his runny come all over her tits and then she worked on getting this young stead hard again and she lifted her legs into an inviting position for him and as he began to rub her wet pussy with the head of his cock and then he backed off and only fingered and ate her into an orgasm...what a let down for all! Holly was sexually frustrated when she got home and I was expecting a sore pussy tasting of cock; instead she took out her frustration on me that night and forgot to tell me about the cum all over her tits (or did she) as I licked and sucked on her tits. Then she tried to push me off and said he came all over my tits and I replied that I could tell and kept sucking her nipples and she moaned more as if she was delighted by this.

This was the last time they met and really it was one of the last times we met with them; Jeff got a girlfriend and moved on and thus this part ended and as Holly told a close girl friend of hers about what we were doing and what happened and another chapter was about to begin.