u/john_chimpo420

Back in my early 20s I used to look at alot of gay porn of all kinds and when I had my first friend who was also curious. He liked femboys and twinks. Well I always wanted to mess around with him so the only times we actually hooked up I was dressed as a femboy. Well I wanted way more dick than my buddy was giving me lol. So I got on Grindr after taking some pics of myself dressed up. First few times I was so nervous about someone knowing it was me because i wasn’t out nor did I act few outside of when I was dressed up for sex. Well one night I found a 38 year old man who was married and he was looking for smooth bttm. I messaged him saying I could host and I was going to be outside on my parents back deck. It was pretty big and they were both in bed. I got a pillow from the house and put it on one of the benches so i could get on my knees and be bent over. I had on a black skirt with pink and black thigh highs and a pink hoodie no underwear shaved from bellybutton down to my knees smooth as could be. I had my hood up with a cute mask 😷 on my some eye makeup on. As he pulled in the driveway I walked out so he could see me and I bent over and showed him my butt . He got out the car very quickly. He followed me to the deck i got up on my knees poking my ass out. I had lube next to me. He dropped his pants and he started running his cock up and down the crack of my ass. His head felt so big I was so excited because his pics looked great nice body and pretty big cock. He picked up the lube then used his finger to rub all over my hole before lubing himself up. Soon as he started to push in me I pushed my ass back on him taking him as deep as I could. He started off slow and deep strokes. Letting me feel all of him. He kept saying he was going to fill me up and said I felt so tight. I was so into it I just moaned and said fuck me. I knew he was getting close because he started to speed up his big balls slapping against my smooth soft ones. He squeezed my ass tight with both hands and pushed in me deep i could feel his cock pumping in me. After he left I went to my room and jerked off with his cum still in me . After that first night with a random hookup started about a 4 year femboy hookup stage for me. I had so many outfits and sexy outfits was so much fun and was always fun becoming someone different for awhile.

Just got pounded out and breed by a man I meet on Grindr. Been horny all day then stuck here at work all night. So I got on Grindr and there was a guy mid 30s like 1000 feet from me. Turns out he was at the gym right by my work. We got to talking and he was fine asf 6foot 190 trimmed beard and hairy chest. Then he sent a dick pic and omg beautiful cock was about 6.5 inches kinda thick with nice big balls. I sent some of mine one with a toy in me and made a joke saying wish it was you. He said he was there alone and he wanted to fuck me in the showers. I asked if he was for real because I could take my lunch break and come see him . He said yes get down here so I leave work pull in the gyms parking lot and walk up to the door and he’s there and lets me in . He says showers are back this way let’s go. Soon as we get back there he pulls out his cock and said suck it . I knew I didn’t have any lube so I made sure to suck him real sloppy before long he said if you want fucked better bend over. I stand up and pull my pants down and arch my butt out and feel him rubbing his spit all over my hole and then pushed his cock in me. It kinda hurt at first with no lube but he spit on it again and he really pounded my ass hard none stop when he came in me was so much that soon as he pulled out you could hear it dripping on the floor. I pulled up my pants as he got naked to take his shower. When I was pulling out there was a truck pulling in lol. 😂 idk why but kinda been hot to get busted

Been real horny lately I’ve been hooking up with some new guys. I’ve been hosting pump and dumps lately. I’ll get all dressed up and then get on the edge of the bed waiting for the guy to show up and fuck me. Last time I thought he was going to never cum. He fucked my ass hard asf for like 20 minutes before cumming in me. Idk what it is but I just love getting my ass pounded then filled up. Anyone else like a good pump and dump? And who else loves feeling cum drip from them

Around 24 I kinda was in my ho faze. I’d hooked up with several guys by this time. I’m normally a masculine guy but in the bedroom I’m a little femboy slut lol. I kept everything smooth that wasn’t covered by my thigh highs and I started to wear a makeup not a lot just enough to look cute. So on this day I had the house to myself because my roommate was at a football game and was going to be out real late. So I got on Grindr and was looking for something new after my Fwb got a little weird. I was only on for like 20 minutes when this 43 year old daddy messaged me. He was a bit taller than I am and had a little belly but not real big and and a hairy chest. We shared some pics and he liked the ones of me in my skirt and stockings and he sent me one of him after he jerked off cock still hard and cum all over his stomach. He was big about 7in. I told him I was free if he wanted to come over. He said he could come by after his wife took the kids to practice. Idk why but when I found out he was married it turned me on even more. I went and got all ready for him got dressed and put a little makeup on. He showed up around 430 soon as he came in I took his hand and we walked to my room he pulled me in close to him and was squeezing my ass tight and kissed me, I started to undo his pants and pull out his cock he was already pretty hard so I dropped down and started to suck on his balls as I jerked him off then started to suck on his cock. He stopped me and said let’s get on the bed he laid down and I started back sucking him as he played with my ass. He had one hand on back of my head and other fingering my hole. He said he wanted me to make him cum so he could fuck me longer. I started sucking him so sloppy while I took turns slobbering all over his cock then his balls. After a few minutes he held my head down and began fucking my face I could tell he was about to cum and boy did he filled my mouth up i managed to swallow every bite of his load. Once i stopped sucking him he came over to me and started to suck on me before turning me over and eating my ass was my first time having my ass ate and I loved it. After he ate me out real good and sucked on me I was so close to cuming. He said roll on your side and he got behind me and I could feel his hard cock rubbing up and down my ass crack before he pushed inside me. He was holding me tight against his body and I could feel his hairy chest on my back. Once he grabbed my leg and spread it by holding it in the air he started to fuck me hard I was moaning so much but what sent me over the edge was him talking dirty in my ear he was so close I could hear him breathing and feel his breath on my neck and ear and when he said he was going to breed me like a bitch. I was pushing my ass so hard against him then I felt something I’ve never felt before it felt like I was about to piss everywhere I didn’t want him to stop fucking me so I just let it go and it wasn’t pee I started to cum and it was the most amazing experience I’ve ever had never have I came that much before my whole body just went numb like I just went limp in his arms I said fuck me daddy and he started to choke me and pound my ass hard asf then he started to go real slow but deep as he could till he pushed in with all his weight and came in me I could feel rope after rope of his cum shooting in me. He pulled out and smacked my ass and called me a good boy i couldn’t move lol he said he had to go and just got dressed and let himself out. Sadly he blocked me on Grindr . Ive ran into him at Kroger and he was with his family. I really wanted him to fuck me again real bad lol

After me and friend stopped messing around I ended up getting a dildo and would put on my thigh highs and thong maybe a crop top and just fuck myself as I looked at porn. Well this only helped so much I knew what the real thing felt like and wanted it again. I’ve heard of Grindr but was always too nervous to get on. I was 23 at the time and had lost alot of weight so I was pretty thin. I was going to have the house to myself for the weekend. So found a really short skirt at lions den and new matching thigh high socks and thong. Soon as I got home I shaved everything that the socks didn’t cover my bush my ass some of my legs smooth as could be. I put on my little shirt and new undies with the skirt and took some pictures. I finally decided to download Grindr made my profile and said smooth bttm looking. Didn’t take long before I had several dudes messaging me. But this one guy stood out from the rest he was mid 30s and had a nice body and a big cock about 7 1/2 inches and thick. He was little over 6 foot, I’m only 5’6. I told him I was looking for someone to come over and fuck me but treat me like a slut. I made sure to get myself all clean before I told him to come over. Took about an hour before he showed up. I was so nervous I was all dressed up for him soon as he got there we were in the kitchen I said fallow me he grabbed me and pulled me to him had his hands up my skirt squeezing on my ass before kissing me I had never kissed a man before but I just melted in his arms he was so much bigger and stronger than me. He said I was going to calling him daddy later. I said I hope so and just smiled at him then we went to my brothers old room had just a queen bed in it. I got on the bed while he got undressed I couldn’t take my eyes off him big hairy chest nice tatted arms then he dropped his boxers nice hairy bwc just hard as can be. He got in bed and told me to suck it. I wasted no time and took him in my mouth as I was sucking him he had my ass up by him and was playing with my hole. I was gagging all over his cock trying to take all of him. He had the nicest balls big balls that just screamed out to be sucked on. After awhile of sucking on his nuts and cock he said he wanted in me. I asked him how and he said he wanted me to ride it but I had never road a cock before but I wanted to so bad so I grabbed the lube and lubed us both up before I got on top of him I could feel his head of his cock pushing into me then felt like he was so deep in me by the time he was fully in me. I was moving my hips and could feel him moving inside me before he grabbed my ass and started to fuck me moving in and out of me so fast I just laid on his chest as he fucked me. After a few minutes he rolled me off him and said get that ass in the air of course I listened to him. Before he put it in me he was slapping my ass with his hard dick. When he put it in I let out a little moan and he said you like that cock don’t you. Something came over me and I said yes daddy and that made him start to pound my ass he fucked me hard asf before pushing in me deep as he could and came in me. I just laid there twitching he smacked my ass and said look at you said I’m a real sissy now. I never hooked up with him again sadly left me gapped and leaking cum

Ok I was 20 and Patrick was 19. We were very close and he would come and stay the night a lot. I had been curious about doing things with guys for a while but kept it a secret. Patrick was very good with computers and I had a nice laptop at the time that I would look up porn on. So one day we was in my room I was on the Xbox Patrick was on my computer. I looked over and he was looking at my cookies on the computer and found the porn I was looking at. On the screen i could see a guy getting head from a man he just said need to learn how to delete my history. I was freaking out so bad but he didn’t say anything negative or make a big deal about it. So fast forward to night time we were both downstairs in the living room. I was trying to get him to come play some video games but he kept saying he was going to pass out. I made a joke about if he passed out I was going to put my dick on him. He laughed and said I better not. I said find out if you pass out. He then said ya ya I could say put it in my hand and you would wimp out . I couldn’t believe what I was hearing I was getting so hard. I said ya right then he just held his hand out and said see. I said leave it there and I would, he put his hand back out and I stood up and pulled my cock out and put it in his hand. He just started to jerk it real slow as I stood there. Then I sat down beside him and could see he was hard too. I said I wanted to see his. He pulled out his dick and was hard asf . We both took turns rubbing on each other before I finally got the nerve to just say it . I told him I would love to suck him if he wanted. I said come to the back room if you want me to suck it. He jumped up so fast. He sat down on the love seat and pulled his cock out. I got on my knees infront of him and started to suck him. I was in shock because I’d thought about this moment for a while now and finally had a dick in my mouth. He said he was going to cum. I wasn’t about to stop this was my first time and I wanted to feel it all his cock swelled up and then he flooded my mouth with cum to this day one of the biggest nuts I’ve ever had in me. I couldn’t swallow it all and let it leak down my face as I kept sucking him. He said wow 🤯 that was intense. That’s what started it all and I sucked him every time he would come over after like the 4th time he finally gave me head to. Best summer of my life I think I sucked his cock 20 times or more before we went any further.

This story happened when I was 22 and my friend was 21 we’re just going to call him Patrick. Me and him were friends for a while and he would come over after work and stay the night a lot. He was the first person I did anything “gay” with. Was the first dude I got and gave head to but that story is for another time lol. So by the time this night happend we’ve been messing around a little. I had hinted at wanting him to put it in me but he was way too nervous. Patrick was about 6 foot 200 pounds and had a nice 6 inch thick cock. We made plans to go bowling together. I noticed he liked looking up femboys and twinks so I got a pair of baby blue and white thigh high socks and a cute thong. I shaved my bush and ass and my legs down to where the socks came to. I had this on under my clothes. While we were bowling I was making comments about if he won he could do whatever he said he wanted to cum in my mouth I said why not my ass. He froze lol but I noticed he was trying to win. I bent over infront of him and he seen my thong he asked and I said I’ll show you later. So once we got done bowling he drove us to this pull off that’s by my parents house. We was going to smoke before going home. He asked if he could see me in my thong and said he dared me to get out of the car and take off my pants so I said he had to get out to and I would suck him off. He said I thought I got to fuck you. I was so excited I had a small thing of lube in the car just in case we needed it and I’m glad I did. So I get out and pull down my pants I heard him get out and I was bent over the hood swaying my ass around. He was rubbing on it and said how smooth I was. I turned around and pulled his shorts down and he was rock hard I sucked on him for like a minute or so and he said if you want me to fuck you better stop that. Told him lubes on front seat and I bent over and pulled my thong to side waiting on him. He came back and he put lube all over his cock then some on my hole before he started to push in. I had to hold his cock and push back on him till he was inside me. He fucked me slow at first then he started to speed up. Didn’t last long before i felt his cock swell up then warm cum shooting in me as his cock throbbed in me. He was breathing so hard and had his hands on my hips and holding my thong strap in his hands. He stoped and slowly pulled out my legs were shaking bad funny part was soon as we got in the car I hadn’t even got my pants on as we were pulling out another car was coming down there lol . He said well if they were like 5 min earlier they got a show. He never said he liked my outfit but whenever we snapped each other and it got to sexy snaps he’s always ask to see me in it and the other time we hooked up I was in it. But that night was amazing he slept in my bed with me and he gave me head and fingered me when we got to my house. Of course I stayed dressed up for him