Jump to content

First time bottoming


Recommended Posts

(edited)

Tell me about your first time taking cock in the ass. 

 

Mine was by a hung latino trans woman. She had this huge uncut 8 and half inch monster. She was beautiful and very passable. I sucked her dick for a good bit until she laid me down on my stomach. She rimmed me at first. Worked a finger in then lubed it up and got 3 in. Then she slowly stuck her giant head into my ass. Real slow and gentle. And very slowly worked it back and fourth. I remember it hurt but also felt amazing at the same time. She took it slow until I was opened up. She gave me poppers so I was rather relaxed. But before I knew it she was straight pounding my asshole and I was asking for her to do it harder. Her cock pounded the inside of my asshole and with each thrust it felt better and better. Then all of the sudden without even touching my cock I blew the most intense orgasm of my life. It shook my whole body. She kept going butt fucking me until she blew her load. It was amazing and Im so glad I did it. I loved being her bitch.

Edited by Deleted Member
We prefer to use the term trans woman, as opposed to shemale :)
  • 1 month later...
  • 6 years later...
That is something I want to try big fantasy of mine for my first time a trans woman
  • 1 month later...
I was all prepared, I'd been using toys for years prior. Steven slid right in. I sissygasmed in like 30 seconds.
  • 1 year later...

Mine was so erotic I met a guy on Craigslist and I got there and I was nervous and we got to his room and my cock was so hard and we started touching each other and then he kissed me and I ripped off his clothes and we made out and then I put his nice dick in my mouth and I loved sucking his cock! Then I wanted him to fuck me so I got on top and slowly got him inside me and I instantly knew I loved riding dick he came in me quick and I loved it and then I began to spasm and moan so loud I was in heaven! I shook and then cum was everywhere and I licked it off and kissed him so passionately

Thursday at 05:37 AM, makeyoucumz3 said:

Mine was so erotic I met a guy on Craigslist and I got there and I was nervous and we got to his room and my cock was so hard and we started touching each other and then he kissed me and I ripped off his clothes and we made out and then I put his nice dick in my mouth and I loved sucking his cock! Then I wanted him to fuck me so I got on top and slowly got him inside me and I instantly knew I loved riding dick he came in me quick and I loved it and then I began to spasm and moan so loud I was in heaven! I shook and then cum was everywhere and I licked it off and kissed him so passionately

wow that is so hot, cant wait to put my dick in a tight hole for the first time

  • 2 weeks later...

The first time I bottomed and got fucked in the butt I came so fast from it XD

  • 2 months later...

Fuck this is hot! I want to be with a passable trans woman

  • 2 weeks later...

I had a sissygasm the first time and cried after it was so intense and overwhelming

  • 4 months later...

My first time bottoming I let a black dude with a 9 or 10 inch cock fuck me. I was super nervous at first but after I had his cock in my mouth the shy factor was gone lol. I ended up riding his dick and he went hard for like 30 minutes in my ass and after I felt that cum explode and fill me even more, I ended up staying the rest of the weekend at his house and he had me wear lingerie and that was the experience that led me to be the submissive slut for bbc that I am

  • 3 weeks later...
April 28, TATTEDnHANDSOME said:

Fuck this is hot! I want to be with a passable trans woman

Do I qualify? 🤪

  • 4 weeks later...

I was 16 and walking by myself at night and a tall beautiful slim woman started following me walking fast and caught up with me.. she asked me did I want my dick sucked n it shocked me and I was a little scared so I told her yes but I was nervous. So she took my hand n led me behind a old empty garage with tall bushes that had enough space for us to be between. It was my first time getting my dick sucked but she just pulled my pants down to my knees and just put my dick in her mouth without using her hand. N she was swallowing my whole dick and I have a big thick dick. But she was holding gripping my ass cheeks at the same time like her mouth was fuckin my dick and when I started nutting my whole body shook because I was standing up while she was swatting down sucking my dick but something hit my ankle and bottom leg hard and I felt wet stuff dropped on my legs and shoe. She was so excited that she was humming and said a couple of times how fat my dick was. N all of the sudden she just sprung me around n I fell on the ground tripping because my pants were only pulled down to my knees. She was very strong and I couldn't do anything but try to put my hands under myself so I could push her off me and all she did was spread my cheeks apart and started putting her tongue in and out my bootyhole n I have a hairy bootyhole and all of a sudden I felt the biggest thing trying to go in my bootyhole like it was the size of a tree! I couldn't see because it was dark plus I was on my stomach! N then she laid on top of my back and put her arm around my neck putting her hand over my mouth and that's when I realized that her hand covered my whole nose and mouth some big hands. N then it went in my ass and I was a virgin. It hurted so much feeling like my asshole was being stretched open by a tree trunk. She was going so deep and going crazy in me until she nutted and it felt like a gallon of milk was going in me. N when she put her face so I could see her eyes she was so beautiful with big juicy lips and long girly eye lashes n I still thought that she was a woman. When she nutted I was looking at her eyes from the corner of my eyes and she closed her eyes and biting her lips until she stopped nutting. When she got up and her dick came out it made my bootyhole make a wet farting noise. I couldn't get up because my pants had my trapped at the bottom of my knees. She pulled me up and that's when I saw her dick. It was hanging down uncumcuzide looking like a long thicker than my ankle with white stuff and a little of my brown boo-boo on the head of HIS dick. N his dick was jumping n bouncing a little bit by itself. I couldn't believe how big it was and that she was a man. She was super beautiful.. but my bootyhole was throbbing and I could feel that it was stretched open hurting and I started to cry a little bit. She got on her knees and told me that she was sorry but she couldn't help herself because I was a very handsome young ***ager boy. N she asked me did I wanted to follow her home so she could clean me up and I did.. she just told me to sit on her chair with arms on both sides and she put my legs on each arm and gave me some baby oil so I could jack off n she started licking my bootyhole putting her tongue in and out my hole slowly and then hard back and forth until I nutted dropping nut on her head and face while she kept on going eating my ass until I stopped nutting. When I left her place and continue walking where I was headed my asshole kept farting and linking her nut! I never saw her again and I didn't get fucked by a beautiful woman/guy again. But I have thru the years gotten pegged by one of my kids mom and a few of my ex's girlfriends. That was the only time I got my asshole fucked and nutted in by a dick n a very big big dick when I was 16

×
×
  • Create New...