u/meatpie420

Me and my girlfriend have been together for about three years. We've talked about cuckolding and I think the biggest problems are that 1.) She's scared that she'll hurt my feelings for real. She's mentioned it multiple times. 2.) She feels like she isn't enough. I don't know if this is a common situation for others, but at one point I maybe talked about it a little too much. Later she talked to me and told me that she feels like she isn't enough as herself. 3). She feels like our sex is so good as it is that cuckolding maybe wouldn't be as authentic for her. 4.) Shes afraid that if we actually do it, that it's the only thing I want to do after that. All the advice is appreciated!

Hey everyone. As you see in the caption, this is the story about me fulfilling my fantasy as a sissy, after years of thinking and fantasizing about it. This happened about six years ago and for some reason I wanna speak about it in a very detailed way so that's why I'm here. (English isn't my first language so don't mind possible grammar errors etc.)

One night I'm sitting at home at my PC, single ass hell and fantasizing about a lot of things. I've been thinking about men especially the last few days and I feel like I finally need to do something about it. So the first thing I do is make another tinder account. Anonymoysly of course because I'm scared about people I know finding out and hoping I find someone before I get banned. Well that's what happens. I start to talk to a very sweet and handsome gay man. We build trust pretty quickly and I find the courage to reveal my identity to him. We schedule a meet up and I'm excited as hell. I've never done this before and never been as nervous about a date as I am know. The plan is that he picks me up from my place and we go to his apartment and drink some wine to calm nerves and see how it goes.

He texts me "come down I'm at the driveway". My heartbeat is through the roof and I'm the most nervous I've ever been. I'm thinking about bailing out but he's already here and I really wanna do this. I wanna lose my "gay"virginity. I go downstairs to his car and get in. We greet each other and start small talk. Its not the most smooth but we are getting there. I ask him if he remembered the wine and he says yes. I'm relieved because I can't do this completely sober. We get to his apartment and open a bottle. We talk for a long time and I start to feel more relaxed and comfortable. The wine is pretty much done so we better get at it. He starts touching my thigh and kisses my neck gently. He rubs and pinches my small nipple (I actually have really small nipples) and it feels so nice and relaxing. He tells me he has some fishnets and heels if I wanna try them. I'm like fuck yeah I wanna feel as girly as possible. He leads me to a drawer and leaves me to change while he goes back to the living room. I change and I immediately feel the horniest I've been in a long time. My cock is rock hard as I walk back to him. He looks at me from head to toes. My upper body has no cover and I'm very naked. I'm only wearing the fishnets and heels. He asks me to spin around and tells me how sexy I look. Compliments my ass and compliments my stomach. I tell him I wanna suck his dick and get on my knees in front of him. He takes his dick out and still pretty soft. I grab it feels nice in my hand. I stroke it a little bit thinking damn I'm really touching another man's dick and I'm loving it. I put it in my mouth for the first and the taste is pretty much exactly like I imagined, meaning it doesn't taste like anything pretty much. It starts to get harder and harder and I'm loving it. I also lick his balls and when he gets really hard I tell him it looks big and feels big in my mouth. I know he loved that haha. I tell him wanna feel it in my ass so I go to his bed and get on all fours. I tell him I think I need to get warmed up and he says of course. He spits on his fingers a little bit and rubs my hole gently and it feels so nice. He asks if I'd like him to lick my ass and I actually say "please do that". He puts his tung on my hole and it feels so wet. I absolutely love it and my cock is already dripping precum. I tell him how good it feels and he keeps doing it for a good minute. I tell him to start gently putting his dick inside me and he does as requested. Then the tip goes in and it hurts. I'm like holy fuck stop right there and don't move. The pain is almost all over so I tell him to keep gently pushing it further and he does. I'm thinking like "damn my ass is really getting stretched by another man no one can ever know". He goes all the way down for the first time and I love how it feels and I tell him that. He also tells me that ass is really tight and it looks so sexy with his dick in it. I thank him for his nice words and tell him to start fucking me gently. It feels so amazing and I've not felt this sexy in a long time. I feel the most confident in years. He keeps fucking me and I start moaning. I tell him to slap me properly and he does. I start to feel more confident every second so I wanna take over the situation. I get off the doggy and sit on the edge off the bed take his dick in my mouth again. His cock is so wet from all the spit and lube (and my juices) and I'm loving every second its in my mouth. I tell him I wanna ride him next so he gets on his back and I hope on his dick like a good sissy I am. I like seeing his face when I ride him because I can see the enjoyment. I switch to reverse cowgirl with my legs under his legs and I realize that riding in that position is easier so I start to go really hard. I ride him like there's no tomorrow and he's grabbing my hips and slapping my ass and we are both really enjoying ourselves and I'm super sweaty at this point and it makes me feel even more sexier. He tells me the wine might make it so that it's really hard for him to come. I honestly tell him I don't mind at all because I'm actually enjoying myself and I'm enjoying his cock and his body and he laughs it off. Then he takes a bathroom break and in the meantime I take a few pictures of myself cause I look sexy and I look like ive been fucked lol. He comes back and the next position is him sitting on the edge of the bed and me riding him again. First I ride him face to face and my cum dripping cock is rubbing against him and he clearly likes it. But I also feel like I'm actually about cum just from rubbing against him and I don't wanna do that cause I'm scared about post nut clarity lol so I ride him with my back turned. My cocks bouncing up and down and my thighes are getting really tired so i have to get off. Then he fuckes me on my back with my legs on his shoulders and his dick goes way deeper than before and I'm like holy shit this is heaven. Thats when I kissed him even tho I promised myself to not kiss men because It didn't feel right but in that moment I really wanted to do that. Then I hang my head from the edge of the bed and tell him to fuck my mouth 👄. He obliges and does it properly. He like actually fucks it and my face is covered in spit and I can only take short breaths but I love it. I feel super slutty and super confident 🩷. Finally comes my favorite. (Btw I'm still wearing the heels and the fishnets). He fucks me prone bone. I'm just laying on my stomach and we are so close to each other. He wraps his hands under my arms and very aggressively kisses and licks and sucks my neck, and of course at the same time fucks the shit out of me till he cums. I'm pretty sure I called him daddy during that asked him to fill me and he did. He makes sure the sperm goes deep lol. All the way down. Then he pulls out and I'm like hey I wanna lick it clean and I do. His cum tasted nice and while cleaning his cock I thank for the experience. Best two hours ever. Then I get dressed, hop on the bus and go home 🏠. I jerk myself off when I get home and I'm glad I didn't do it at his place because the post nut clarity really hit me different that day. But that's my experience 🤭

Thank you for reading 🩷 (I have pictures)