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It all started when I had a sex dream about one of my colleagues. I worked as a waitress in a small restaurant at a camp site as a side job while in college and one of my colleagues, David, was really open and flirty towards every female employee there. I didn’t really think much of it, and we didn’t talk often one-on-one, but I started to dream about him. There was this dream in which I was giving him a handjob (even in my dreams I didn’t have any penetrative sex) but it felt so real. It really got me hot and when I wake up I masturbated in the shower shortly after.
Not too long after that my boyfriend and me talked about our fantasies in bed. He asked me if I ever fantasized about anyone other than him. I was a bit cautious since I didn’t want to hurt him and I gave a general answer like “doesn’t anyone” and “don’t you”. He confirmed that it was something natural but asked about specific examples. I really didn’t want to talk about it at first since I was worried it was some kind of trap question. He kept pressing so I reflected the question to him. He opened up and told me he was off course curious since he only had done sexual things with me but that he had wondered in the past how it would have went if he had taken things further along with his ex (with whom he dated for a while but never got past a French kiss). I recognized that he was cautious to tell me too, but I immediately confirmed to him that that was all natural and that I understand it. Then I told him about my sex dream with David, still a bit cautious since my fantasy was more recent and with someone I actually saw regularly while he hadn’t seen her in many months.
But to my surprise he kept asking about it and my feelings and if I had ever masturbated with him in my thoughts. When I hesitantly confirmed that, I saw he was really hard (we were in bed already and were wearing pajamas so it was really visible). Somewhat puzzled and weirded out I asked him if he got horny because of my fantasy for another man. He told me he was and to be honest I felt both a bit of disgust at first as well as a bit of hornyness myself. So I asked him “so you wouldn’t mind if I did something with another guy?”. I think he saw the surprise combined with a bit of disgust in my voice so he immediately said “I didn’t say that!”, “I just find it hot that you have fantasies”. But the tone of his voice betrayed him as much as me before. The difference was that I had a weapon he didn’t: I placed my hand on his pajama pants and squeezed in his penis. “Are you sure?” I asked him. But I saw he was a bit terrified so I let it rest a bit, Kurtköy Escort while I got his penis out of his pants and jerked him, while talking more about fantasies in general. But although I jerked him very slowly he came within a very short time (probably about twenty seconds) while there are/were moments in which he could last for more than ten minutes. I didn’t told him then or before but a guy cumming fast (incidentally) is one of my fetishes, so I got really horny after that too. A few minutes later we were both satisfied and cuddling while having conversations about other subjects.
About a week later we again were in bed, fondling each other for a bit while naked and I brought up the subject of our fantasies again. While I was stroking his penis I said I noticed that he came really fast that time a week before. He mumbled something about having done little himself in the week before that, but I knew he could last longer, even if it was a while ago that he came for the last time, so I kept pressing. “Did you find it hot that I fantasized about another man?” I asked. He denied. “I always find it hot when you tell you masturbated.” I knew that was true since I didn’t do that very often till I met him. I grew up rather conservatively and my previous boyfriend was really insecure about it. When I met him and he repeatedly assured me that it was okay, that he even found it hot that I did it without him, sometimes asking about it when we were doing stuff (especially when I was jerking him), I grew into it and started doing it rather regularly, I actually got my first orgasm while masturbating. But then again, when I normally said I masturbated the night before, he didn’t came in seconds so I didn’t believe him. I said to him that I found it hot how we were talking about our fantasies and that I wanted to do it again. I asked him about the thing he most wanted to try and he talked about very general stuff like specific positions and things like that but nothing actually hot or perverse. He then asked me and I recognized the only way I could get him to talk would be if I told him something perverse I wanted. So I said a MMF-treesome would be hot but that I didn’t expect it to ever happen regardless because I would never do a MFF-threesome “since I’m not a lesbian”. To my surprise he answered that he wouldn’t mind doing that once we could have sex. I asked him if he wouldn’t want a FFM-threesome in return but he denied that.
“You really wouldn’t mind?” I asked. “No, to be honest I think a threesome with two guys is hotter than a threesome with two girls.” Kurtköy Escort Bayan – “Wouldn’t you mind sharing me with someone else? You know you would have to watch me get fucked by someone else right?” – “no, I really wouldn’t mind. I actually would find that kinda hot”. I was still stroking him slowly while we were having this conversation and I noticed him getting really hard and twitchy. I knew I was onto something. “So you were getting very horny the other time when I was mentioning my fantasy with another guy?” – “yeah…” he hesitantly said. I tried to keep an open mind and asked him more about it. “Why?” – “I don’t really know” – “you don’t really know?” – “no…”. This went nowhere and he got very red. My attitude the last time didn’t help and I needed to console him that it was nothing bad. I told him that I really didn’t mind and that I found it hot that he had a fantasy too, even if I didn’t fully understand it.
The thing that puzzled me the most was that he had the fantasy of me doing something with someone else, in a MMF or otherwise, while we didn’t even had PIV sex yet (due to my vaginismus I mentioned in an earlier post, we only did hand- and mouthstuff and I couldn’t do anything more by that time). As open and understanding as I could I asked him exactly that; why like that while we couldn’t even have “real” sex. Very red in the face and hesitantly he told me that he really didn’t know but found the thought very, very hot. I don’t know if he actually didn’t knew why or not but I knew that he was friendzoned a couple of times and later found out that his previously mentioned ex drunkenly told him about the guys she kissed and implied doing more while they were still dating and he only kissed her. That actually was one of the reasons he broke it off with her, she was kinda mean but they also had different thoughts about what the relationship was. But I didn’t knew that then. I still didn’t really understand but was genuinely interested in his fantasies. I noticed that his penis got a bit softer/flaccid so he got really uncomfortable.
I tried to be more understanding, pulled my hand from his penis and said “you know, I really wouldn’t mind helping you in your fantasies if you can be open towards mine too. But you really have to tell me what they are if you want that.” That was when he told me about his cuckold fantasy. I didn’t knew there was such a thing until then but I looked up all kinds of stuff about it afterwards. He told me he likes to hear about people having sex in general, that he previously masturbated to stories Escort Kurtköy his friends told him about their experiences with sex, that it probably had something to do with him being a virgin (he was almost in his mid-twenties and the farthest he had come before me was a French kiss) and his high libido (which he had, we had sex about four times a week then and still he masturbated regularly). He told me he is kinda voyeuristic but never done anything with that and he told me he found me to be the hottest girl he knew and that he would fantasize about me with others as if it were porn. I didn’t really understand that last part but I found it to be flattering. Another thing was that in the beginning of our relationship I used to talk about my exes a bit too much. I sometimes compared things or told him stories about them. Sometimes he said he didn’t like that and so I quit doing that, understanding that that can be very annoying. That was also I reason I didn’t understand it, since he brought that up and said he sometimes fantasized about me and one of my exes.
Especially since they had penetrated me and he didn’t since my vaginismus issues developed later in my relationships. My first boyfriend had a very small dick which meant it all got a bit easier which explains partly why I didn’t have so many issues with that. At the end of our relationship I couldn’t trust him which made it harder to have sex for me, which I blame for my later issues. My second ex had a larger penis so the pain progressed and my current boyfriend is larger than both of them (he actually has a really impressive, thick penis, which is part of the reason I was afraid to have penetrative sex with him, especially after we failed at it a few times). He said he fantasized about them fucking me and thinking through some of the things I said about them (I told him about some of the times I had sex with them but very superficial). I asked him If he wanted me to talk about a story of one of them while I gave him a handjob and he nodded very heavily. So I told him about the time we had sex seven times in a three day weekend. I didn’t get far though since again he came within a minute.
After he came and cleaned himself off, we talked about it for a bit and I told him that I really didn’t mind talking stories about my exes, just that I didn’t have that many special ones. We didn’t really talk about the other stuff but the seed was planted into my brain. I found it hot that I could get him off so easily with my stories and that he fantasized about me while he didn’t mind me fantasizing about others. I still was a bit cautious though, especially since my first boyfriend was very jealous while at the same time cheated on me at the end.
I will end it here since it got very long as it is but I will talk about our first actual experience with cuckold (still only hand stuff) and the prelude to that a next time.
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