First Penetration

[bamrule]

Hello all, I am interested in your first time experiences.

Share your stories of first time cock entered your ass, what did it feel like, the exact moment of the first penetration?

I remember my first time, she helped me prepare with some toys, then, she put her cock on my hole and started pushing slowly, when the head got in I knew it I was addicted for life, she was all the way in, and when she started pounding me... oh god...

[Cereal Escapist]

My first time was neither good nor bad. I was a college student and decided to spend the $ on an escort to live out all of my fantasies so I was definitely too anxious and preoccupied with the $ iI was shelling out and making sure I hit every note to actually enjoy it.

We did it without preparation and very little lube. It didn't hurt as she was about 6" and somewhat thin so I just relaxed and took it in, but all I can remember is me rushing through the motions. Obviously, future endeavors, after I got over my issue of paying for it and also realized that I'm supposed to be enjoying it, not rushing it, were far more enjoyable.

[IluvemHung]

I remember my first. And it was actually a black GG that was posting as a Transgender woman. And top of that she was jacked and muscular lol! And she had this thick strap on toy. I was all nervous and new and shy. And she started out with a rub down that was pretty awesome and she was fingering me pretty deep. But the thing with strap ons and dildos are they are very dense and solid unlike a real penis that bends and compresses at least a little. She started to insert the strap on and thrusted forward and I was screaming! That shit hurted and I was done! She was like, "Come on quit being a pussy and let me fuck you. You know you want it." I was sure at that time that taking it in the ass was not for me! But the trick is practice, some whiskey and a girl that is patient and not monstrous in size and it can definitely feel good. What I know now is with Tgirls that sometimes if the length doesnt get you then there are Tgirls out there with girth that might be too much or vice versa.

[Highlander1963]

My first time was about 10 years or so ago in Edinburgh with a couple. She was a GG who was a don and the TV was also very Dom. They took their time, bound and gagged me with a sort of rubber ball on it. The GG lay back and I had to go doggy with my mouth and the ball thing pushing and licking as best I could at her pussy. She held me head gently whilst the TV lubed me and very slowly and gently moved inside me. My experience now is that TV was very good as had a very big cock but it didn’t hurt at all it was done so smoothly. Then fucked me slowly and then quicker for at least 20 minutes, my arse was quivering but with the GG stroking me hair and pushing her pussy against me it felt amazing. The TV then withdrew, took off the condom and the gag from my mouth and came in my mouth.
They then rolled me into my stomach, tied my hands and feet together and wanked me off, a mega cum. I have been addicted ever since. Have to say though, there are many lesser endowed TS and TV than my first who really hurt even after all those years , so it just goes to show that the first time isn’t always the sorest, it’s who is doing the penetration that makes the entry easy or otherwise.

[Highlander1963]

Just remembered, the TV was called Laura, was a flat up near the Usher Hall and is probably more like 12-13 years ago. Back in the days of the ads being in the old Sunday and Daily Sport!! Not sure where they went, but certainly that first penetration convinced me that was what I had been missing in my sex life up till then. Thank you Laura.

[must93]

My first was with a Latin TS that was 9 inches and very aggressive. She was very hard knowing it was my first time being a bottom. She took me doggie and took her a little while to get all in me. It did hurt but after a while WOW. I knew I was hooked after that. She used me for about two hours in different positions. Was great.

[gaysian71]

I was 21 my first time. I wanted to get with a trans girl sooner, but they all said I was too young. Even when I finally got my first girl, she asked to see my ID to be sure I was over 18.

I met her at a club in the city called Divas. That was a club I discovered when I was 17 and couldn't wait to get in. So I finally got in after I turned 21. I forget her name, but I'll never forget the feeling of being penetrated. I told her I was a virgin, so she went kind of slow. She undressed me and told me to get on my knees. Then she pulled out her cock from her panties. I'm pretty sure the moment she pulled her cock out I got hard. She was big, but not super big. Probably around 7". I took the head of her cock in my mouth and immediately knew I loved it. I got her good and hard. Then she told me to get on the bed doggy position. Then she lubef me up and gently pushed her hard cock a couple inches in me. I told her it hurt and she told me to relax and enjoy it. I did relax, but it still hurt for a few minutes. But after a few minutes it started to feel good. Really good. She had me moaning like a whore. Eventually she moved me on my back and continued missionary position. By that time I was rock hard. She reached down to grab my cock and it didn't take but a few strokes for me to fun. But damn, I was so turned on. After that I was done. All in all it was probably 20 minutes. 15 minutes of sucking and stroking her cock and maybe 5 minutes of her fucking me. But after that night I couldn't get trans girls out of my mind for months. It was incredible.

[IluvemHung]

They key is douching well, enama like where your bowels are flushed and lube up. Or use a insertable relaxant. Other wise that, "I have to take a shit feeling," will be overwheming. Relax. And for some reason smaller cocks can hurt more than bigger cocks, I think it depends on how hard or rigid the girl's erection is. IDK.