Cuckolded by my Childhood Bully
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This is about my girlfriend's first date with someone who I'm going to call "Bully." I call him that because when we were younger he bullied me a lot and now that we are in our early 20s he doesn't anymore but still we both remember our places. We're friendly and I had a dream where he fucked my girlfriend and I couldn't shake that for months. So I asked my girlfriend if she would try a date with him. We had talked about cuckolding for a long time and she liked the idea but was nervous as expected. She didn't know he bullied me and so when I pointed out and "old friend" she said yes.
I then told Bully about our situtation and he smiled and told me to tell her to give him a call. She did and they went on a date.
Their date went well. She told me he behaved nicely unlike all the times I remember him acting. They had lot of fun together and he did not try to do anything inappropriately.
She thought he looked hot, she was nervous during the whole date in the start of the date. But he did get her comfortable. She told him he was the second guy she had gone on date with after me and he was surprised about that and told her that he was lucky she gave him a chance. During the date he kept touching her, nothing inappropriate but she was aroused by his touching.
Before dropping her off at home in his car, he kissed her and asked her if he could come inside. She told him her parents are home. He kissed her again and this time it was a more passionate kiss. He touched her body and tried to touch her boobs. She let him touch her side boobs but stopped him from going further. He asked if she did not have fun with him. She told him she had fun but it's their first date only and she doesn't feel it's appropriate for first dates to go further.
He asked her if she will be free the next day, they can go on a date again and she agreed. He dropped her off and helped walk her to gate and kissed and hugged her again.
After reaching home she chatted with me and told me all about her date. She told me she was so wet when he touched her inside the car it took her best effort to stop him from going any further and she was going to take a cold shower to cool herself.
Their second date went great. He picked her up for the date near her house. At that time I was with her to provide her emotional support and to watch her dress up for the date. I watched from across the street as she got into his car. I popped a boner when I show her gave him a light kiss on the lips.
I thought about following them on their date but by the time it would take me to reach home, and borrow my parents car, they would have already gone. Decided to go home to satisfy my boner.
He asked her if she wanted to go to club but she told him to go to a cafe because she wanted to talk to him and get to know him. He was touching her the whole time and she became a bit aroused by his touching. Afterward they went on a drive. He took her to a lake in our town. That lake has nice view and joggers path but mostly known for the young couples who makeout there.
At first she was reluctant to allow him to touch her boobs but as they continued to make out her resistance decreased and she allowed to him to touch her boobs. He started to slide the strap of her dress and bra when she stopped him and said not here. "Let's go to my house," he said and before she knows it she was on her way to his house. She was aroused and her nipples were poking out of her bra.
While driving he kept rubbing her thighs. She told me the whole ride she was nervous and was conflicted if she wanted to go to his house or not. Halfway towards his house she said sorry to him and she can't go to his house today, that she was not ready. He asked if she did not like today's date and guilt tripped her into coming to his house. He said they can hang out in his place, if she doesn't feel comfortable he won't touch her. She said she has known him for only 2 days and doesn't feel comfortable in his place.
On the way back he asked her if she was a virgin, she told him she only been with one guy (me). They talked some more and he kept rubbing his hands on her thighs and moving it higher and higher. He told her he was tired of driving and could he come in her house since it's her house she does not have to worry about him doing anything inappropriate.
She told me his constant touching and talk broke her barrier and she told him to wait for 10 mins, she will open the back door and they will sneak into her room. After saying hi to her parents she sneaked him into her house. She did not want her parents to know because they will think she is having sex with him and it would be embarrassing especially in front of her father and them knowing she is dating me.
She asked what he wanted to do. He said she won't agree to what he wants and if she likes football they can watch world cup highlights. He wants to see the German team lose. They put highlights in her macbook but it was soon forgotten after they started making out.
He did get her out of her dress but she did keep bra and panties on. She allowed him to rub her through her panties but not more than that. She felt his penis through his underwear. I asked if he was bigger and she nodded. How big, she said don't know since she did not see it but it was much thicker. My heart was broken but my penis was still solid.
They made out for close to an hour until all the humping and rubbing made him have a semi orgasm. The wetness in her hand broke them out of a trance and she told him he should leave now and she made sure her parents were not watching and got him out of her house. He asked when can they meet again, she will msg him.
After reaching her room she smelled her fingers and that made her horny and she took off the rest of her clothes and masturbated as hard as she ever did, giving herself an orgasm and then needed more. So she was still naked and snuck out to the bathroom and used a shampoo bottle to finish herself off. And then she called me and told me about her day. While taking to her she also had one more orgasm while I came twice but the second time my penis was too exhausted from jerking off the whole day and was only semi erect and no cum came out, only 2 transparent drops.
He messaged her and asked if they could try morning jogs together and she agreed to go with him if he keeps his hands to himself and he replied no promises. Usually I am not a morning person but this morning I got up early, looked for my jogging clothes that have not been used for a while. It took me sometime to find them. I was unable to keep up with them so I sat on a bench and saw them from there. Once they reached my bench she stopped and look at me, he also looked at me.
He told her to continue jogging and that he will talk with me for old times sake and will catch up to her soon. He gave me creepy smile and told me what happened in past is past and I don't need to bring up the bullying past in front of her. I was a bit scared and nodded. He said I look tired so I better head home while squeezing my shoulder. I didn't know if he was squeezing hard or if he was using his normal force. Then he ran to her and put a hand just above her ass to turn her towards the path. She waved bye to me and I watched them together for some time before I left.
In that moment I had mix emotion, if I wanted them to continue or not but just after 2 mins my boner was back in full force.
This morning I went to her house and watched Westworld, a new episode together but for the first time I was unable to concentrate on it. I was just imagining her together with him. I asked her what happened in morning she told me nothing. They just kissed once. She asked what did he say and if I am okay with her going to jogs with him because I hardly go one in a week.
I said he was just sorry for some mistakes of the past and not to tell you about it.
Afterwards we had sex while talking about her date.
Beto & Lisabeth
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