I had one girlfriend in high school and college, who was almost single handedly responsible for all of my cuckolding fetishes. For the sake of this story, let's just call her Colette.
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I think I was in love with her the first moment I saw her. She made me work for months just to get a date, really made me squirm, work and grovel. She was gorgeous and very outgoing, very flirtatious, funny and extremely popular with other men. The type of girl who instantly attracts guys without any effort. I never really understood how i got with her in the first place but we were together for more than a year. She was a year behind me in school and we began dating during my senior year. When I left for college, it really opened up a crack in our relationship. More on that later.
Before we became a couple, she had a long relationship with one of the wrestlers in my school. He was a big brawny athlete with a cocky arrogant demeanor. His name was Tim while mine is Tom, pretty close.
She also had an ex named Brian who lives in the next school district. The one that included the local farms. Brian was a farmers son, in other words another well built, big talking Alpha type.
Other than constant flirting with other guys, the first cuckolding behavior was when we would make out or eventually have sex, she took my virginity btw, she would occasionally call me Tim. Like I said two very similar names so I let it slide. I didn't realize I was setting up boundaries that she would constantly push. She saw that calling me Tim got a rise out of me and she always had a curious smile while gauging my reactions. She seemed to get a kick out of it.
On two separate occasions with two different friends of mine, she played kind of a game of tag while holding onto my friends arms and crying out for them to protect her from me which they both did. Again, this seemed to really thrill her.
She was naturally dominant to me and was the very first person i experimented bdsm with. She loved to handcuff me and tease me mercilessly including tickling which I really hated. She also enjoyed having new clean her feet with my tongue. She loved to walk barefoot so they were always filthy. She had trained me well.
When I began college, my first roommate was Craig. Medium height, dark skin and hairy. Really arrogant and loud. When Colette would visit, he works always stare and make any comment her felt like making.
Once I gay into a bit of a financial pickle and Craig offered to land me the money to fix it. He had plenty of it. I had zip. His famous line was "I'll let you work it off for me". I really needed the money and also I am subby minded so I agreed without any question.
The amount of money was over 100 dollars and in the mid eighties that was quite a chunk of change so he put me to work.
He seemed very comfortable being in charge and bossing me around. Basically told me that from that point on, I was his Schneck, which is a Jewish term for a slave.
I was in charge of typing out any homework he had, washing his laundry, keeping the entire dorm room clean was upto me and I basically did whatever he said.
There was a store 2 blocks from our dorm room. He would make me walk there to buy him cigarettes. Walk all the way back then send me back for something he "forgot" one time, making me do it 4 times but I had really little choice.
He was the type that enjoyed humiliating others. I really put myself into a precautions position with him.
Meanwhile, Cilette and I would joke about the fact that Craig really liked her and she wanted to try to play a joke on him. she wrote me a fake letter, confessing that she really had feelings for him. And she wanted me to put it in my dresser with a small piece of paper on top, because I knew he was going through my drawers, she wanted him to find that so we could tease him and play a prank on him.
Sure enough, the next time I looked, it was obvious that it had been moved and he must have read it. When I told her this, she became extremely excited, very interested in every little reaction he had, and she wanted to continue next time she visited.
She had no idea about the prior arrangement Craig and I had with the money he lent me. she was completely oblivious to that situation.
It was understood between us that it was a private secret thing or so I thought. The first time Colette visited me after the letter incident.l, things were a little bit different in the room with the 3 of us. Instead of toning down the behavior he took the opportunity to boss me around in front of her. at first I didn't know what to do. So I just did what he said, although she kept giving me really curious questioning looks.
He then took it upon himself to explain the situation that he had loaned me the money and that I was doing him favors in return for the semester.
As I had feared this greatly interested her, and she asked him to tell more and more about it, not talking to me just talking to him now. While they both discussed me, I felt small and humiliated. I also said nothing in my own defense.
She had a very cruel streak. So she started asking him to prove it and he would have me do things and I continued to do them while they both laughed in ridiculed me
I had lost power of the situation immediately and was now acting the fool for both of them.
They both are getting more and more excited by my display, as I sunk further and further into humiliation, not knowing how to get out of it.
Send Craig ended that tension and worsened it in with one sentence. He told me to walk to the store to get them cigarettes and wine coolers. She loved the idea and even added some to the order.
I couldn't believe this was happening. I certainly didn't want to leave her alone with him, ever For any length of time, but they both just stared at me, Daring me to defy them both and being the sub that I am I caved, then walked out of the room. I hated this damn guy and I was going to willingly give him alone time with my girl. That was insane, I had to hurry.
I ran to the store, but there were a couple people there, so it took five ten minutes for the transaction, and then I ran back.
When I re-entered the room, the atmosphere was different. They were laughing and having a good time complained that I took too long.
After I serve them, their drinks and cigarettes, Collette pointed out that there was nothing to eat in the room. Craig had an immediate solution. Guess Who was trotting his way back down to the store to get snacks? And they didn't just want any snacks. They wanted snacks from Krispy Kreme, which was an extra 3 blocks away, but again I obeyed.
Unfortunately, this trip was more like a 1/2 an hour, so he really had time to work on her. I was desperate to get back and make sure nothing was going on.
As soon as I rounded the corner into the hallway of my dorm, I saw it hanging there in the door handle, a sock. The universal sign that the person inside was shall we say occupied. It meant someone was being intimate and they did not want to be disturbed period what the fuck man what the hellwas I supposed to do I couldn't believe itI couldn't f****** believe it. And other people in the dorm saw it and were wondering who craig was in there with. I said I had no idea.
I didn't know what to do. In the past, If that happened, I would simply sit in the floor outside the door so that's kind of what I did, I was actually hoping maybe I would get to hear something. I was so conflicted, but in the end, I was aroused and that sucked. So I sat for about 15 more minutes then decided I had had enough and I tried the door, locked of course and my keys were inside.
One of the most humiliating moments of my life was when I had to knock on the door and ask them to please let me in.
Finally, it was Colette who opened the door looking at me with an almost annoyed look, her clothes disheveled, and her hair was a mess, they had clearly at least made out. God knows what else. he was smug, and smiling, as I handed him his booty, literally.
They both played it off like they were just talking and nothing happened. But clearly there was an uncomfortableness in the room, and I had somehow become the third wheel. She said it was probably the time that I took her home, so I walked her back to her house. Not saying much. She was embarrassed and didn't know what to say either. Which was bad because normally she would joke and tease me but clearly something had happened and she didn't know how to deal with it. Hey kids goodnight was more of a peck on the lips.
When I got back to my room, Craig couldn't have been smugger, he had a whole list of things that he wanted me to do and I just started doing them. I never questioned him or defied him. He had one more step of power over me and he knew it, and it was starting to affect me in ways I hadn't expected. I kind of liked it. I have to admit to this day, every fantasy I ever have of a mystery man with my wife has Craig's face and his name. Actually, in fact, my wife has cried that name out many times as I've gone down on her because she knows I hate him and that it would cause pain.
Craig actually transferred after the semester, so I was free and I was glad he was gone. Although he is now permanently tattooed on my psyche.
After a semester at school collette and I decided to slow down a bit and just date other people but still be together. This kind of hurt as we were pre-engaged, and I thought we were going to spend our lives together but again, whatever she wanted.
During her senior year in high school, Collette worked at a bookstore in our local mall. I would go to visit her there and outside of her store was a bench that we would sit and I would bring her lunch during this time. She started to see a guy, Dave, who worked at a store, 3 or 4 stores down from hers again, a real jerk. Whenever she'd be with him and we'd be together. She tasted like beer, but would deny it.
This dude's best friend Mark was a manager of the shoe store directly across from Colletes bookstore. One especially painful occasion happened when I brought her lunch. I went to kiss her and she put her hand and stopped me and said, no, mark will see, and tell Dave. I reminded her of our time together and that we were a couple but she didn't want Dave mad at her. That Stung badly.
Perhaps the biggest cuckolding act that she did to me, the one that really hammered on the final nail on this fetish into my head came between her and her ex. Brian, the farm boy.
Collette remained very good friends with Brian's sister, Tracy and the 3 of us hung out quite a bit. One time, we dropped Tracy off at her house and I had pulled all the way up a long half mile driveway, up to their house that sat at the top of the hill overlooking the road and I had backed in right in front of the garage.
While we sat there talking, Brian arrived home in his big orange Bronco and pulled all the way up in front of the house and backed in right in front of my car, so I had nowhere to go and couldn't get out.
He cockoly strolled up to the passenger side and leaned in and talked to Collette for quite a while. Then he told her he had something he wanted to show her in his truck. She asked if it was okay if he went with him. And what could I say? Of course, I said yes.
So she went and climbed in his truck with him. And they were in there for at least a 1/2 an hour, and it was difficult to see what was going on. the entire time this ordeal took place, Tracy sat in the car with me, talking about how much women had a hard time getting over Brian, and they always came back. How she was surprised that I had lasted so long with Collette, and she hadn't gotten back with Brian, yet. How this may be the opportunity for him to get her back. She just sat there teasing and taunting me the whole time that was brutal, and yet I was pinned my seat.
Tracy knew my personality very well. To the point where as she sat there, she kicked off her shoes and put her nylon feet up on the dashboard, putting them up against the glass. As she spoke to me, I was in some weird hypnotic world, sinking deeper every minute. If she would have plopped them into my lap and demanded, I rub them, I would not have hesitated. She was a natural botn domme same as Collette.
At one point just to harass me, Brian started up his bronco and drove all the way down the the driveway to the road where he stopped. I sat there, wondering what was going to happen if he got out into the road and drove away, I was going to drive home and just let her go. But instead, she must have told him not to do it, and he backed up and drove all the way back up and she emerged from the Bronco. Again, disheveled.
She was already a little bit drunk. When this ordeal started and clearly, she had some more beer and she stumbled a bit, she got into the car and I drove her home without a word between either one of us. She never did disclose what happened in the back of the bronco.
Oh my darling Collette, she single handedly turned me into a cuckold slave and I have never recovered and never will.
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