r/gayconfessions • u/Sea-Purchase-3196 • 2d ago
Sugar Daddy Had a Sugar Daddy for a few months NSFW
I’m currently 28 and a bi bottom but this happened a few years ago when I was 25. At this point I was only out to a few people, my roommate being one of them as he was gay and a couple of his friends who had become mine as well. At this point our lease coming to the end and unfortunately my roommate had got a new job and was moving in LA quite suddenly. Since He was leaning we weren’t going to renew as I wanted my own place, I was making enough to afford one but options were very limited at the time so I was likely going to have to settle for whatever is available.
During this search I had started talking with a sexy older daddy type. He was in his late 50s handsome clean cut very well dressed and appeared quite rich. He was 6’2 very fit and lean muscular with dirty blonde hair and clean shaved. He told me he splits time between LA and NYC as he moving for work to LA in a few months. We made plans to meet with he got back to NYC and the day finally arrived and I went to meet him at a fancy cocktail bar. I wasn’t really out at this point so honestly going on a “date“ with a man was mot something I was super comfortable with but he was hot and I really wanted to hook up.
I arrive and find him a table kind of tucked away in a private corner. He stood up and gave me a hug, he squeezed me tight and smelt amazing. As nervous as I was he was so charming and seductive that any nervous went out the window. Talked about work life, goals and eventually have a couple drinks moved more sexual and love life. I told him I was bi only out to a few people but becoming more comfortable with it, how I mostly had sex with me and also told him about my living situation. He was single, never married gay most of his life, had a few long term relationships but they weren’t for him. In the most seductive voice he told me he needed “a sexy younger man to have when I want my needs met… and they are often” At that point I think I let out a whimper and goosebumps ran up my body. We finished our drinks and he suggested we go back to his place.
Luckily he lived right around the corner in a beautiful brownstone building Right on the first floor. The apartment was a huge 2 bedroom with a big livingroom and even a dinning room. He told me he bought it years ago and planned to keep it even when he went to LA as he would be back in NYC often. It wasn’t long during the tour before he came up behind me pulled me into him and whispered in my ear to “strip for daddy”. I followed his order as he he groped my body saying how sexy I was before pulling me into him and making out with me with such power and passion. I was melting in his arms as he started to undress revealing his amazing body which I started to caress. Finally He dropped his pants and out feel his beautiful thick 7.5 in cock (he had it listed on his profile) and I immediately went to town sucking him right there in the kitchen. He was calling me such an eager slut, show daddy how much I love his cock.
we eventually moved to the couch and he sat down stroking his cock with lube and he told me to ride his daddy cock. I straddled him and squatted down onto his cock and before I knew it i was driving up and down him riding him like a bronco. The way his cock curved and the angle I moved to his cock was slamming right into my prostate. He gripped my hips guiding me up and down telling me how sexy I looked taking daddy’s cock, I think he could sense it and told me to cum for daddy. The way he spoke was so seductive and the way his cock was fucking me I exploded all over him, he kept guiding me up and down as my orgasm kept going almost tearing up at this point and he started to grunt as my hole clenched around his cock and told me he was going to breed me. I barely got out the words “breed me daddy!” And he did just that, his cock shooting his load into me as he roared, the grunts he made as he came were so hot but also it was like his whole body was feeling it, he was convulsing shaking as he cock throbbed inside me. Making a man react like this was so hot I almost came again lol. Finally he came down pulled me in for a kiss told me how good I did and as we were nose to nose said “i think you need to clean up the mess son”.
I smirked as I got up down his cock started but liking my cum from his chest and abs and eventually moved down to his cock, sucking off all the cum still on it and what left as I came off his cock even getting it off his balls. He was loving it, saying how good of a slut I was and how he was going to have to keep me around. I told him I’d love that daddy and we made out more, he got up made us a couple cocktails and we sat there naked on the couch chatting more. At some point I didn’t even realize I started to stroke his cock again and before I knew it he hand me bent over the couch fucking me hard and with such power until he bred me again. As I did before but this time without being prompted I dropped to my knees and sucked hsi cock clean. He smirked and said I was such a properly trained slut.
We exchanged numbers and I went home, definitely walking funny but couldn’t stop thinking about him, maybe because I felt his seed still leaking out of me. A day later he said I should come over that night and he had a “proposition for me”. I had no idea what he was going to say but was excited. I arrived at his place he handed me a cocktail as he was already naked and told me he was a bit of a nudist and I dropped my clothes. We sat on the same couch he fucked and bred me twice and he went on to say how he prefers to have consistent sexual partners, not necessarily to date but when he’s in town a sexy son who can take care of his needs and knows how to properly. He added “I was also thinking about your living situation and thought of a possible solution“ I really had no idea what he was going to say next but was truly shocked. He said since he’s only here every other weekend, I could stay full time at his place until I find the right place for myself instead of having to settle. I said that’d be amazing daddy thank you. He stopped me and said if I did I’d have to be make sure I was taking care of his “needs” when he wants a blowjob or to fuck me I did it. I laughed and grabbed his cock and said I’d me more than happy to help and started to suck his cock. We fucked again that night two more times before he sent me home full of his seed. He also told me he would be out of town for the next month and that he had a storage unit I could keep my things in while I stayed with him.
My roommate had already moved to LA when he was back in town and he even arranged to have movers take care of my things. When I finally got to his place I immediately stripped and within seconds was on my knees sucking his cock. After another round of fucking we had dinner and drinks and as we were he slid me a credit card telling me he likes to take care of his sons and to use it as I pleased. I said that wasnt necessary this is more than enough and he told me no, save your money, I have more than enough and like to spoil my son.
Over the next two months I was completely living at his place and any days he was in town I he was fucking and using me like a ragdoll and I loved every second of it. He encouraged me to update my wardrobe, he sent me to a custom suit place he used. This man was spending thousands of dollars on me, my food, my bar tabs my clothes. Part of me felt kind of like a whore but also I knew he actually enjoyed it and I was more than happy to give him my holes. Even after he moved fully to LA I stayed at his place for a couple months until I eventually found a spot that was perfect. During that time he’d make trips back to the city and I was always there to be his slutty eager son.
We keep in contact til this day and still see each other when he’s in town.