Ch. 01 A Breakup Changed Everything

I am a cuckold. For a long time, I felt ashamed of my thoughts and desires. I struggled to stop the thoughts from creeping into my head but always failed. How can the thought of another man being with my girl be so exciting. If I figured out how it all started, maybe I would be able to undo everything, so I started to write everything I could remember.

I was 23 years old and my girlfriend of almost 6 years, Suzy, had just dumped me. I fell in love with her in 9^th grade and after over a year of pursuit, she accepted my advances, and we became each other's first relationship of any type. I was always proud of how my hard work and persistence landed me someone who was obviously above my caliber.

We met at our church's youth group. We were extremely active in our church and community. You name a weekend, and we were either helping with youth and young adult groups, facilitating weekend retreats, or hanging out with our church friends... every weekend.

We were virgins at this point. We had decided to wait until marriage before having sex. That didn't mean we weren't active, it just meant we didn't' have any form of penetration. We moved slowly through all the phases in our exploration from the first kiss to going down on Suzy. She never reciprocated with oral sex, but it never bothered me. I just felt lucky to be able to have a girlfriend with such an amazing body to enjoy.

Throughout our time together, she was always flirting with guys. She couldn't understand why they would always hit on her and pointing out the fact she was flirting always resulted in denial. I honestly think she just couldn't understand how her smile, body language, and touching would come across as flirting. I always tried my best to not be the jealous kind, but it was difficult to say the least.

Suzy was 22 years at the time of our breakup. She was the obsession of one of her college classmates, Paul, for almost 2 years. He was engaged at the time, but it didn't deter him from hitting on Suzy daily. Since they were in the same undergraduate program, they spent a lot of their time in and out of class together. Their group of friends would hang out at each other's house after school, go to the beach on a regular basis, and talk on the phone at all hours.

The thing that reassured me was the fact that Suzy would tell me everything he would say or do. She never tried to hide anything, and I believe she was oblivious to his intent.

During one of her physiology classes, they were paired up with classmates to trace the muscles and tendons on each other's legs. Taking turns, one laid on a table and their partner would feel the other's muscles. At one point, while Suzy was face down on the table as Paul worked on the back of her thing and knees. Then he kissed her thigh, not once but twice, and she pushed him off with a giggle.

As you can imagine, I was dying on the other end of that phone conversation. What I remember most is her not having addressed the issue with him and then being upset with me because I was upset. Her defense was, 'How can I make him feel bad when he is going to be in every class of mine for the next 2 years. He is also part of my close group of friends, and it would make it awkward.'

A few weeks later, she broke up with me. Apparently, I was too jealous of a person and it was affecting her school focus.

Fast forward about 10 months and she reached out to me. She wanted to get back together and like a lovesick puppy, I jumped at the opportunity. I had convinced myself that I must have been the fault of our breakup with my jealousy, so I was grateful to get another chance.

A few weeks into our re-kindled romance, she broke down crying. It took almost 15 minutes for her to calm down, enough to tell me that she lost her virginity. My brain splint in two. Half was freaking out and the other half wanted to console and reassure her everything was ok. I was still a virgin and even though we were no longer together at the time, felt betrayed and couldn't reconcile what she had just told me.

For the next couple weeks my mind was like a beehive of emotions and questions. I couldn't bring myself to ask any of them without coming across as being jealous. After all, that is what she thought I was.

In one of our nightly phone conversations, she asked me if I was ok with what she had told. I asked how she felt about losing her virginity, how she felt now with me still being a virgin, and various other innocuous questions. She explained that she didn't want to rush our relationship and wanted to wait a little longer. The lovesick puppy just nodded and accepted it.

In a later conversation I started to ask detailed questions. The what, the who, the where of it all. As the weeks passed, my questions were more intense. I needed more details. Often, I would repeat the questions. My heart raced with every answer and my stomach twisted. I hated it but I needed to know.

Suzy kept asking if I really wanted to hear the truth and I insisted. I believed if I knew every minute detail then she had no secrets left. The more I knew, the less personal it was for her. At least, that is how I justified my interrogations.

She had been introduced to Jason through a mutual friend, Tammy. He was a bit older than Suzy and they hit it off. On their 2nd date, he took her to a drive-in movie which I didn't even know still existed. In the back of his SUV they started making out and halfway through the movie they were completely naked and he was positioning himself to go inside.

She stopped him and explained how she was still a virgin. He went ahead and had her jerk him off and drove her home.

The next weekend, he took her to dinner and then drove into a private park and pulled up behind some trees. They went to the back of his SUV and the same scenario unveiled. After a long time of kissing and heavy petting, he started to slide her skirt up and rub his hand over her wet panties.

"Wow, you are so wet.", whispered Jason and she blushed with smile.

He started to lift her shirt exposing her bra and then he pushed it up until the breasts popped out. Suzy remembers how he sucked on her nipples for what felt like 20 minutes. In the meantime, he had pulled his shorts and underwear off and was stroking his cock without her realizing it.

He placed her hand on his cock. Then he held her hand and moved it closer to her pussy. He knelt in front of as he was hunched by the car's ceiling. He kept her hand on his cock as he pulled off her panties. She was caught off guard when he lifted the up to smell them and then threw them into his back seat.

At first Suzy thought he was going to masturbate as close to her as possible and then cum on her but then she saw him opening a condom wrapper. She admitted she didn't want to look prudish after having stopped him the last time. She knew Paul dated hot girls that were very promiscuous, and she didn't want to be seen as a slut but also she didn't want to look like a nun.

Jason was smart. Earlier he had left a set of photographs in his car of a girl he had been dating and she was, in Suzy's words, a model. When Suzy mentioned this, I told her it was his intent to make her doubt herself. I had never met him but the way she described him, he was about 6'2" with a six pack, and very athletic. The photos had Suzy comparing herself and she admitted she didn't want to look prudish.

She was so turned watching him stroke his cock as he slipped the condom on. She began to slowly close her knees together. She was more nervous than afraid. Suzy pressed her legs a bit tighter and when he finished putting his condom on, he gripped her knees and gently spread her legs apart. She didn't resist. Embracing him while and kissing him deeply, she prepared for what she postponed for 22 years. Everything was a blur.

It was killing me that she didn't remember every detail, but what she did remember was getting me hard.

She remembers him being gentle, but she thinks it was because it was her first time. It was painful and took a while to push his cock inside. Every time she winced, he stopped and started up slowly again.

My obvious questions at this point involved his size. I will admit I am not well endowed. I'm barely 5 inches and not very thick. I can get the job done but up until this point, I didn't really have anyone to compare myself to, so I had always thought I was above average.

Jason was about 8 inches and twice my girth. I remember Suzy commenting about how large I was when she had never seen another penis and now those conversations seemed comical and depressing.

She went home sore that night.

It took 3 weeks with another man for her to lose the virginity she kept for over 6 years with me. Of course, I was conflicted and angry. But I was also a little turned on.

On another call, she shared her second encounter. I had never even thought of asking how many times they had sex. I was just so wrapped up in the whole "virginity" aspect, it never crossed my mind.

Once again, my stomach was twisted in knots and my body started to shake as we talked.

Tammy and her boyfriend invited Suzy and Jason to a local hotel to just spend the night, go out on the town, and have some fun. Tammy worked for the hotel and would often get free stays when they had cancellations.

Jason and Suzy were lying on the bed while Tammy and her boyfriend got ready to walk around the hotel and check it out. Suzy had wanted to join them, but Jason didn't want to go. As soon as they left, Jason stood up at the edge of the bed, took off his pants and just looked at Suzy. This was going to be her first blowjob and she was very nervous. She slid to him on the bed and began to kiss the head of his cock and gently put the tip between her lips.

She didn't think Jason was very satisfied because after less than a minute, he put his hands on her head, and moved her head to let him slowly go in and out of her mouth. She tried to keep up but was flustered and even gagged at times.

I realized as she was describing this scene, my body was still shaking but my cock was rock hard. I had no idea what was going on. I was still very jealous and upset but it was feeling good.

He pulled away and stared at Suzy.

"Take off your clothes!"

Suzy mentioned that their friends might come back.

"Take them off!", he repeated.

She did so as he stroked his cock. This was the first time she really saw his cock and realized how much bigger it was than me. It took me several times to get her to admit this. She kept avoiding my questions because she didn't want to hurt my feelings but then she quickly added that she loved me and not Jason. I don't think she realized that didn't make it any better.

He pulled her to the edge of the bed, gripped her legs and pushed them up as close as he could to her head. He was looking down at his cock as the head rubbed her labia and then he made a comment about how hairy she was. She doesn't think he was trying to insult her, but she remembers how self--conscious she felt. I told her I loved her natural bush and then asked her to continue.

It took some time for Jason to push into Suzy and this time she had a good view. She could see his head pushing into her very slowly. It wasn't just her being tight, it was the thickness of his cock. He never pushed his whole shaft into her.

I had been stroking myself the entire time and with that I came and had to pull the phone away from my mouth as I grunted. It was dripping on my thigh, and it kept coming out. I can't remember cumming that hard or that much. Why is being so upset and jealous a turn on, I remember thinking.

Then I asked her if he wore a condom this time. She had to stop him and remind him she was not on birth control, so he pulled out and quickly put one on, but she could tell he wasn't planning on it.

That same weekend, Suzy asked Tammy why he was so timid with her after hearing all of Tammy's stories about his dating life. Tammy had explained to her how he was quite the player and usually dated more provocative and slutty girls. Tammy wanted him to date Suzy because she thought Suzy would be good for him and he would quit being such a man-whore.

"Jason thinks you are a 'good girl' he finds it hard to be his normal self with you during sex. His words were 'Innocent'. The whole virgin thing threw him off and he didn't want you to freak out in the bedroom."

I asked her how that made her feel and she admitted she was pissed but she probably would have been out and extremely self-conscious not knowing what to do.

Two months into their relationship, Jason sort of broke things off. She said she wasn't hurt by it. A long time later, she confessed Tammy told her the truth.

"Jason thinks of you as the type of girl you get married to and he isn't looking for that right now. I'm sorry for setting you two up."

They had sex several more times but they were just vanilla versions of the same.

Every few days a new question would pop up in my head and I would bring it up during our phone conversations. Every time I would ask for more details. Every time I would quietly jerk off.