1st time u bottomed

[AlohaShannon]

The first time I bottomed...I remember it well!

I met a transwoman online maybe 10-11 years ago. I went to her place purely for a hook-up. When she opened her door I was surprised by how thin she was...not sickly thin, just naturally very petite. She was moderately passable but certainly cute. We made out on her couch a little before heading to the bedroom. I was so incredibly nervous I had a hard time "rising" to the occasion myself. She on the other hand, had no problem at all. My jaw hit the floor when I pulled off her clothes and an enormous cock leapt out at me from behind her cotton panties. I was flabbergasted at the thought of the first dick to ever go in my ass being a whopping 9 inches with a CRAZY curve to the left. Despite my growing fear, I was mesmerized by what she was packing...I mean seriously, it was so beautiful!!! Not only was her cock incredibly gorgeous, but she was very capable with it as well. After blowing her to completion once, I decided it was time to pop my cherry.

She laid on her back and I straddled her. On my first attempt to put her inside me, I was forced to stop IMMEDIATELY as the pain was excruciating. She soon realized that she was going to have to take this into her own expert hands and she laid me down. She patiently lubed me up from the inside, slowly using one finger, then two. When I said I was ready, she lifted my legs and ever so slowly slid her massive cock into my ass. I can remember every single moment....my back arched, my mouth opened, and I let out a quiet groan as I felt dick inside me for the very first time. Though I felt quite a bit of pressure, it was truly the most amazing thing I had ever felt sexually up to that point in my life. It felt as if every pleasure center of my body had finally been awakened. I jerked myself while she continued to slowly fuck me until I came with such force I think I lost my vision for a few seconds.

So, the first time I bottomed was heavenly...even with a huge dick with which I was forced to contend. Although I must say, I had the overwhelming urge to shit the entire time and am grateful for even the limited use of toys I had up to that point.

Since then, 3/4 of the guys I've slept with have had huge cocks (like 8 inches + and girthy). To be quite honest, the ones that feel the best are the average sized ones...especially if they have an upward curve.

Sorry for getting too detailed, I really like writing about sexy sex!

[LJay]

For the newcomer it would seem that this may be more a matter of girth than length. The anal sphincter is essentially a round muscle and that is what is being stretched first.

[Insertnamehere]

The first time I bottomed...I remember it well!

I met a transwoman online maybe 10-11 years ago. I went to her place purely for a hook-up. When she opened her door I was surprised by how thin she was...not sickly thin, just naturally very petite. She was moderately passable but certainly cute. We made out on her couch a little before heading to the bedroom. I was so incredibly nervous I had a hard time "rising" to the occasion myself. She on the other hand, had no problem at all. My jaw hit the floor when I pulled off her clothes and an enormous cock leapt out at me from behind her cotton panties. I was flabbergasted at the thought of the first dick to ever go in my ass being a whopping 9 inches with a CRAZY curve to the left. Despite my growing fear, I was mesmerized by what she was packing...I mean seriously, it was so beautiful!!! Not only was her cock incredibly gorgeous, but she was very capable with it as well. After blowing her to completion once, I decided it was time to pop my cherry.

She laid on her back and I straddled her. On my first attempt to put her inside me, I was forced to stop IMMEDIATELY as the pain was excruciating. She soon realized that she was going to have to take this into her own expert hands and she laid me down. She patiently lubed me up from the inside, slowly using one finger, then two. When I said I was ready, she lifted my legs and ever so slowly slid her massive cock into my ass. I can remember every single moment....my back arched, my mouth opened, and I let out a quiet groan as I felt dick inside me for the very first time. Though I felt quite a bit of pressure, it was truly the most amazing thing I had ever felt sexually up to that point in my life. It felt as if every pleasure center of my body had finally been awakened. I jerked myself while she continued to slowly fuck me until I came with such force I think I lost my vision for a few seconds.

So, the first time I bottomed was heavenly...even with a huge dick with which I was forced to contend. Although I must say, I had the overwhelming urge to shit the entire time and am grateful for even the limited use of toys I had up to that point.

Since then, 3/4 of the guys I've slept with have had huge cocks (like 8 inches + and girthy). To be quite honest, the ones that feel the best are the average sized ones...especially if they have an upward curve.

Sorry for getting too detailed, I really like writing about sexy sex!

You should consider writing erotic novels man. That was hot the way you describe your experience!

[AlfredM]

I can always expect a saucy hot story from you [MENTION=20680]AlohaShannon[/MENTION] . Damnnn!

[AlohaShannon]

You should consider writing erotic novels man. That was hot the way you describe your experience!

Thanks! Unfortunately, I don't think I have the patience to write an actual novel. I would just want to get right to the sex parts and bypass any plot building.

[AlohaShannon]

I can always expect a saucy hot story from you [MENTION=20680]AlohaShannon[/MENTION] . Damnnn!

Haha, thanks Alfred! And I'm keeping the things I write as tame as possible...imagine if I wrote everything that I REALLY wanted to share!!!

[Insertnamehere]

Thanks! Unfortunately, I don't think I have the patience to write an actual novel. I would just want to get right to the sex parts and bypass any plot building.

Scripts for porn, then! Duh!

[AlohaShannon]

Scripts for porn, then! Duh!

Haha! Maybe I'll just write a sexual conquest memoir with ALL the explicit details, kind of like Tucker Max (I think that is his name) and Chelsea Handler.

[ballparkdogg]

On the football team in high school, another teammate and I started playing around with each other. Since my mom was never home, we spent hours and weekends sucking each other. He started eating my ass which lead to me bottoming. Then he spent every free moment topping me.

[Joerogers225]

On the football team in high school, another teammate and I started playing around with each other.  Since my mom was never home, we spent hours and weekends sucking each other.  He started eating my ass which lead to me bottoming.  Then he spent every free moment topping me.

Thats really hott!! I started to mess around with boys probably when i was around 9 or 10 I started, all my same age. We would kiss and suck a lot but it never turmed into anything else. I have always topped in my adult years and am looking to transition into bottoming! Any tips fellas?