February 4 8:02 PM Me and Clarissa had a serious fight today. She wants me to go down on her after I cum when we have sex. I didn't understand it at first but after arguing back and forth for an hour she finally told me that my cock is just too small and I cum way too quickly. That she never had an orgasm with me because of this. I never knew she was such a shallow, hurtful person. I felt so lucky when I first met her. A smart and beautiful girl like her noticing me let alone talking to me was such a big surprise. And now here we are. After two years she is telling me my cock is too small and I cum too fast?! I can't believe her. I can't believe how she is playing the victim, crying and telling me to "talk about it". After humiliating me like that? No way. February 19 3:43 PM It's been two weeks and she still hasn't apologized to me. All she does is making cruel remarks about how I never help with anything. Whatever. My dad never had to do the dishes or clean the house for my mom. Why would I do it for her? It's literally her job not mine. Mine is to provide financially. And I know, she makes more than I do but that's only until my hentai artist career takes off. I even got a commission last month and once I get more popular I'll be filthy rich. February 24 10:13 PM I'm done with her. Actually writing this from a café. Today I went out to buy new headphones and when I returned home she was waiting for me in the living room with some wannabe fuck boy sitting next to her. She's never had friends over before but whatever. Then she dropped the bomb. It's her lover. What the fuck?! I am her lover, not this gym rat. When I told them this the guy started acting all tough. But Clarissa was still playing the victim, trying to look sad. Telling me how selfish I was and that she needed the comfort. The bitch. She even told me I could stay because she likes me still but this guy, Josh or whatever, will be her lover from now on because I can't satisfy her and refuse to even try. This asshole even laughed when she said this. Fuck them both. Like I was gonna talk to her after humiliating me like this. I left and will not be going back. March 4 7:59 PM I had to move back, temporarily. I know, I know. But I had nowhere else to go. I tried to ask friends but apparently I don't have any close ones. I only had money to rent a motel room for eight nights. Also I was unsuccessful in hooking up with girls. Just like before Clarissa. But since I wasn't a virgin anymore I thought it was gonna be easier. But nope. All those mean bitches were calling me fat or short or ugly. There was only one that was gonna let me fuck her but when she saw my cock she laughed and told me to leave. So now I'm back with these two living in the guest room but not for too long. March 6 1:02 AM Today something weird happened. Clarissa told me I could watch Josh and her having sex and I can even jerk off if I wanted. She told me she felt guilty about cheating on me. At first I thought it was the most fucked up idea I've ever heard but I haven't gotten any action in more than a month now. I figured it would be more humiliating to her new boy toy to have her ex still linger around anyways. So I eventually agreed. I sat in a chair naked as they fucked on the bed. They didn't even look at me once. But Clarissa was acting like she never did before. With me she always looked bored but with him she was in ecstasy. She was moaning and screaming his name. I'm not proud of this but I came three times during the whole thing. I watched them do 69, him pounding her from behind and her bouncing up and down on his rather large cock. I was jealous for a moment but then I realized she must still like me if she invited me back so he's the loser after all. March 6 7:35 PM Clarissa gave me an ultimatum today. I don't get it, yesterday she was all nice but now she is against me again. She said I could stay only if I helped with the chores. This isn't fair, I'm not a fucking maid. But she also said that I will still be allowed to watch them have sex if I wanted to because apparently I was "really enjoying myself" last night. I was furious but after calling a few people I had to realize again that I had nowhere else to go. Whatever, this is temporary. I'll wash the dishes a few times and I'll be out of here as soon as possible. And I can still watch them fuck in the meantime. I have to admit I kinda like it since I still couldn't get any girl to sleep with me so without this my sex life would be pretty boring. March 20 2:58 PM I'm getting pretty desperate. No new commissions for my art. No Tinder matches. All I can do now is sit around, do some basic chores, and jerk off all day until it's time for Josh to bang my girl. Then I'll go into the bedroom, watch them and cum like two or three times. Not the absolute worst but I could really use some money and some real sex. March 29 11:54 PM Today Clarissa and Josh confronted me. I really don't like it when they put me on the spot like that. They sat me down and told me that they were getting tired of me not doing my chores properly. That I spend all my time masturbating in my room. How I was only allowed back if I help them out. And how I should be doing all the chores since I'm the one without an actual job. And then they suggested the most outrageous thing I've ever heard. Clarissa showed me this small plastic thingy with a ring and a tube. She told me it was a chastity cage. And they will only let me stay if I put it on. Apparently it will prevent me from jerking off because me cock wouldn't get hard in it. I was so humiliated and so angry. I just stormed off. Took some of my stuff and went for a walk. I tried to call people again but no one was willing to let me stay with them. Not even my parents. They told me I was too old to live at home and that I should get my shit together. So I reluctantly went back home and agreed to do that thing. Clarissa told me to strip naked. Josh was laughing the whole time, making comments about my fat body and small dick. I got hard instantly which made him humiliate me even further. Clarissa meanwhile was silent, waiting with that thing in her hand. After trying to put it on unsuccessfully she gave me a tissue and told me to jerk off into it because I must be soft for it to work. It was so embarrassing. But again, I had no choice. I jerked off and came in under a minute. She then put on that device. She pulled my nuts through the plastic ring and then put my cock in the tube and locked it. Then told me that from now on I'll do all the chores and if I do a good job she'll help me get some relief. I was grinning like crazy. It looks like she still wants a piece of me after all. March 30 1:10 PM What the fuck? Now they are walking around naked all the time?! I woke up this morning and when I went to pee I came across Clarissa. She was butt naked. She smiled at me and said good morning. The she just cupped my balls and gave them a playful stroke like it was nothing. What the fucking fuck is going on? March 30 9:40 PM And now they are fucking like wild rabbits. In the living room, in the kitchen, in the pool, everywhere. I tried not to play along their little mind games but after a while I just couldn't help but watch. My cock was twitching like when you are wearing tight jeans and it tries to get hard but can't. I hope it won't get any worse but I really don't want to clean the house. April 8 9:12 PM It's getting worse. I can't take it anymore. I see Clarissa naked all the time, I see them fuck and she is teasing me on purpose by flicking my caged cock or pinching my nipples randomly. I decided to talk to her yesterday. Telling her that I don't want to play anymore, just let me out and I'll leave. But she convinced me to just give this a try. Just do my chores and she'll relieve me of all my frustrations. So I started doing everything they told me and in two days I was done. I cleaned everything, did the dishes, did laundry, everything. Clarissa was really happy and told me I'll get my reward tomorrow. April 9 11:20 PM I had my first milking today. I was hoping she'd let me out and fuck me but no. I had to get on all fours on my bed first. She then started smearing lube into my asshole. I started protesting but she just told me to try it once and that I really should get milked regularly. I then told her to just let me out. If she doesn't want to fuck me then fine, I'll just jerk off. But she told me I've already masturbated enough for a lifetime and it's not like I've seriously proven anything yet. Helping out once is not enough. She explained that she will drain my prostate so that it won't be full of my cum and that it is for health reasons rather than pleasure but I will also feel a lot better afterwards. What the fuck did she mean by all of this? But whatever, I figured it can't be that bad, I'll play along until I can figure out a way out of this. So after lubing me up she pushing her finger inside. She was probing for a while then seemingly found something. She started massaging a specific spot and suddenly I started dripping my cum on the bed. It didn't feel like an orgasm. It wasn't satisfying or anything. But she was right, I felt some relief when she was done. June 12 10:34 AM It's been two months. I'm getting better at my chores and Clarissa regularly milks my prostate. I miss jerking off a lot and sometimes I try to bring it up but they always tell me that they can't trust me with my own cock. That I will just play with it constantly again if given the chance. I always go silent because it's not like they are wrong. But all of this is still humiliating. I try not to be around them too much but whenever I am they are teasing me. Clarissa touches me, Josh mocks me, all the same shit. And my tiny cock just wants to get hard, but it can't. Even with the regular milkings I'm getting more and more frustrated. July 8 3:48 AM Clarissa told me today that she is tired of having to constantly milk me and that she wants to put an end to it tomorrow. I have no idea what she meant but she sounded so serious she really creeped me out. I can't even sleep. What does she want to do to me? November 24 8:10 PM I started writing this diary years ago to chronicle my then soon-to-be sex life and now this is my final entry. I just re-read the last one and there is a good reason for the long hiatus. My life completely changed the day after writing my last entry in July. At the time my ex-girlfriend Clarissa was keeping me in a chastity cage and would milk my prostate once or twice a month but at one point she told me she didn't want to do it anymore. The next day they put something in my drink at dinner because I fell asleep at the table and woke up tied to my bed and to my surprise my chastity cage was gone. I was scared and angry so I called out to Clarissa and Josh so they came in and she had this weird tool with her. She explained to me that she will crush my nuts with it so that I won't have to be milked anymore. I thought she was joking at first. I asked to be let go but she told me they needed me to do the chores for them as they were busy with work and their love life and were planning to start a family. She sat down next to me and I saw in her eyes that she was serious. I started begging but she just ignored me. She took my balls in her hand and told me how much easier my life would be without them. I won't have to wear the chastity cage anymore since I won't even get hard. I will never want sex ever again. Moreover, my small penis will shrink and will probably retreat back into my body. I was crying, telling her that I didn't want any of this and that I still wanted to cum or maybe even have sex if I get lucky. But she just smiled and told me it'll be quick and I won't miss them once they are gone. She was right about both of these things. She crushed my balls one after the other in about two minutes and that was it. My life is different now. I got a few weak erections in the weeks after she took my balls but couldn't really jerk off due to the pain and discomfort. By the time I healed my erections disappeared completely. In the following months my cock did indeed shrink and is now a tiny button rather than a penis. I can't have orgasms, not that I really want to. Clarissa and Josh are nice to me now, I still live with them, not that I have any other options. Where else could a eunuch go? I do everything now around the house, I'm kind of like a live-in maid. But it's not like I'm bored or anything. And once the baby arrives I'll even have new responsibilities. Now at least my life amounts to something unlike when I was a jobless loser with a tiny cock.