The Road to Humiliation!
I have always been a dude who tried very hard to hide my insecurities. I have always been thin, not the tallest, not in a great economic situation and not very good around women. Before entering college I had sex only once with a girl. I was accepted in a college I could afford and right from the start I predicted it would be boring as fuck. My only friend at the time, Sam, went to another university where he quickly made a ton of friends and I started seeing him less and less often. I guess his new friends were much cooler than me and by the social media posts I saw how his college life was going great.
Now Sam tried to include me into his new group of friends a bit but they seemed all assholes to me. Muscular, arrogant, rich dudes who used to drive nice cars and get the hottest girls. To be honest I envied their life a lot and even tho I couldn't stand them I went out with them from time to time I guess to join the cool dudes club. They had a lot of girls around them but I wasn't able to score.
One summer after our second year in college Sam invited me to go on vacation with him and his friends. They apparently rented a nice beach villa and I joined them a couple of days later.
I met them at the beach where the four of them were having some drinks under the sun with 3 girls. They looked like the usual college chicks but they were incredibly hot. One of them in particular caught my eye, Jessica.
She was wearing a black thing bikini that day and my god she turned me on so much. She was beautiful, very slutty face and behaviour and she was all over one of Sam's friends. I saw them make out a lot and felt extremely jealous. We spent the three remaining days going to the beach, drinking, staying late and partying all night and back at the villa I would hear how Sam's friend made Jessica moan like crazy.
Every day the girls were dancing, having fun, letting them grab their asses and stuff, but I was too shy to do any of that. Sam told me those girls went to college with them. We talked about how hot they were and he told me he was the one introducing Jessica to his friends after he fucked her for a week. None of them were the relationship kind of dudes so of course they would pass them around. On the other hand Jessica and her friends just wanted to have fun by hanging out with muscular and wealthy dudes. After that vacation ended I got back to reality and to my boring college life.
Almost every day I would jerk off thinking of Jessica and how hot she was. I would think of her friends too but mostly it was about her. Seeing her body, how she acted like a total slut with Sam and his friends. Those girls were out of my league but also very different from what I was used to.
4 months later Sam organised this big house party for his birthday and I was invited. All the people there were from his college so I didn't knew anyone. Sam was all over the place so I stayed mostly alone until I noticed Jessica. She was wearing this short black dress with high heels. She looked amazing. I had no idea if she would even recognise me but as soon as she saw me she came towards me and have me a hug. She smelled so good. We chatted for a couple of minutes before a dude came and took her away. I followed her with my eyes all evening as she drank and danced with him and other people.
She was the same slut I remember from summer but I was crazy after her. I saw her shaking her ass, letting him grab whatever he wanted and then saw her going outside with him. They went behind the house and idk why I decided to follow them. I tried to be quiet and saw him staring with his back on the wall while she was on her knees sucking his cock. I saw them for about 10 seconds before he noticed me and told me to fuck off. I moved quickly so I was sure she didn't noticed who I was.
I went back inside and straight to the bathroom. I had to jerk off. The image of her sucking his cock made me so hard and I came in seconds. I felt so pathetic but being pathetic was becoming a normality to me.
I got myself a couple more drinks and then I felt a hand touching me. It was her.
We started chatting once more and I asked her if she wanted to go somewhere else as the music was too loud for me to hear what she was saying. She asked me if I could take her home as she felt pretty tired.
We started walking to her place which was like 20 minutes away. We talked about school, relationships and stuff in general and although she was a total slut she wasn't as dumb as I thought. Or at least it was the fact that I was obsessed with her that made her look brighter in my eyes. I took her home and that was it for the night, I got a kiss on my cheek for that but she also gave me her number.
We started texting and talking once the phone regularly in the next weeks.
I learned that the dude she blew was just a guy she used to fuck and that she didn't have any serious relationship in her life. I could tell her body count was pretty big and also that she seemed quite a gold digger as she really enjoyed going to fancy places, buying fancy clothes all with men's money. There were a ton of red flags there but I fell in love with her. When talking with me she showed me her soft side although she didn't try to hide how she kept having sex with other dudes.
I could tell she liked me too, but maybe she also knew I wasn't in her league and she didn't want to start anything with me.
I was thinking about her all day while still jerking off to stories she would tell me about her. The day I felt very bad was when Sam posted a story on snapchat of him at a party with Jessica siting in his lap and him grabbing her big boobs. I felt like a total idiot. Of course I jerked off again and again seeing that video. I tried from time to time to ask Sam about her, never mentioned I was actually talking to her but I wanted to know things she did. He told me he has some videos and photos of him fucking her and also his friends fucking her. I asked about other girls too as I didn't wanted him to notice I was interested only to Jessica.
I tired to push him around a bit for him to show me those videos and pictures. I asked him to show me what crazy stuff he had done with his group of friends and he started showing me.
Most of the pics and videos were of them partying, drinking, dancing with girls. He showed me some hot chicks he fucked and then a cam video of him slapping a girl's ass and then as the video went on I noticed it was Jessica sucking his friend's cock while Sam kept slapping her ass which was resting on his lap. My heart started racing but I wanted to look cool and not like some sort of pervert.
I acted like it was just a video like the others. Then I saw another video of him fucking her doggy style and some other of Jessica and her friends topless. Then some pics of her tit being squeezed by him and a few others. That night when I went back home I sat in the living room and wanted to jerk off, but as I was ready to start Jessica called. I answered the phone and started talking with her. I was so horny I just wanted to do it but she wasn't saying anything erotic just telling me about her day.
I tried to slowly push the conversation a bit to see if it could go sexual. I asked her about her body count in like a joke, like a truth or dare and she told me it was around 20.
We went on with questions and she asked me what was my size. Now my cock is nothing impressive but usually I would at least lie just a bit to girls. I would often say 6, 6-5 although it was more like 5.5. This time tho I wanted all the humiliation. I knew she had tried much bigger ones and from the video I saw of her both Sam and his friend had much bigger cocks than me. I told her it was 5 inches and she was quiet for a bit. I asked her if it was that bad and she tried to make me feel good and told me stupid things like size is not the only thing that matters and bullshit like that.
My cock was hard as a rock. I asked her what was the biggest she ever tried and she said it was about 9 inches. I was quietly jerking off so I joked about how she would probably not even feel mine if I went in after the 9inch guy.
She started laughing and told me that was probably true and then she said I could still use my tongue tho. Hearing her say that I came all over my stomach making a real mess. She noticed what was going on and asked me if I was pleasing myself. I was so ashamed. I tried to lie and say I just spilled a glass of water but she knew exactly what was going on. She started laughing and making fun of me and honestly I felt very bad.
She noticed and moved on. We talked a bit more about other stuff and then we went to sleep. All those weeks of talking and we never actually hanged out. She always found justifications but I kept seeing from her socials and those of Sam and his friends that she kept going out to parties and stuff. One night I was hanging out with Sam and after a couple of beers at a bar, his friends called him and invited him to join them. They were at this other bar which was a 10 minute walk.
As we arrived we saw a group of like 15 people, girls were there too and then, I saw her. Jessica was sitting there with one of the guys. She smiled at me but didn't say anything. We all sat and stared drinking and talking. I remained quiet on the edge of the table and saw the guy next to her having his arm around her. She saw me behind uncomfortable and I saw in her face she didn't wanted me to see her with that guy. I left earlier and that night she called me pretty late. It was around 2am and she woke me up.
She asked me why I left early and if she did anything. I told her she did nothing wrong and then she asked me if it was about her being with another dude there. I told her I wasn't her boyfriend so she didn't have to worry about that part. I was talking to her much rougher than usual and this got her angry. She told me she just wanted to know if I was ok and asked why I was acting that way. I started complaining about how I knew I wasn't enough for her and shit like that and she told me I was an idiot and hung up. She called again 10 minutes later and asked me if I expected her to leave the other dude and just grab my hand, take me home and fuck me.
I told her she wouldn't do that because she knew I wasn't good enough and that she would have more fun doing that with that other dude. She told me I was so insecure and that was my problem. I was still angry with her and asked her if she fucked that guy that night. That pissed her off so much that she started telling me she did. She said she had a big cock and made her scream like crazy, in a way I could never. She started mocking me telling me to start masturbating just like the last time. I was so fucking embarrassed. She asked me if this was what I wanted to hear. She kept telling me how he filled her pussy and how my small cock is too pathetic.
I was so turned on by all that humiliation that I left my pride aside and started to jerk off. I told her I was doing it and she kept telling me how pathetic I was. How my friends are all better than me and sex with them feels so good. I came so hard that night. After that her sexy voice turned into a serious and disappointed one. She told me I was a pathetic loser and hung up. The post nut clarity was tremendous. I couldn't sleep that night. I was so ashamed that I stopped talking to her. She texted me a few times to apologise but I never responded.
Weeks later I saw she had blocked my number and from her socials. I told myself I had to forget about her and about all that happened. I avoided places she could be in when Sam invited me out and stuff. About 5-6 months later I started to feel better. I wanted to make a change. I started going to the gym and as college was coming to an end I just wanted to find a nice job, find me a nice girl and start a life.
Everything was going pretty well for me after graduation. But I still can't shake my time with Jessica. I feel such a pull to get that drug like feeling again.
Max Insecure
MORE CUCKOLD COUPLE POSTS
Becoming a Kinky Hotwife
I Find Guys for her while she is Blindfolded
I Watched her on Video
