Ever tried to cross to the other side?

[badtube]

Long story short:
I asked Yoshi to dress like a woman and fuck me. He said he preferred to be bottom, but agreed to top me, since it was my first time.
He suggested that I should straddle him, so I could control the penetration better that way in case it hurt. I thought that made sense and we went to the bedroom and got naked.
I asked him if I could kiss and taste his cock, since i never had done that before as well. He said he would like that very much. I did first kiss it and than tasted it with my tongue, eventually taking the whole thing into my mouth and just frenchkissing it as i did his tongue before. His groan let me know that he enjoyed it. After a little while of that he told me to stop if I didn't want me to come yet.
He put on a condom and we used a bottle of shower gel for lubricant
I placed my knees on either side of him took a hold of his beautyful cock and guided him into me.
It felt so good, it hurt some, but in a good way.
Just when he was all the way into me there was an "accident" .
He slipped out and it felt so wrong.
Shit, I felt nauseous and thought I had to go to the toilet.
I quickly excused myself and ran to the toilet. Sat on the bowl but nothing would come.
After a short while he came to the door and told me that this was not unusual for the first time, and that he felt sorry.
I assured him it was not his fault, but i was still feeling sick and totally de-sexed.
After a while I was certain that i din't need a bowel movement and got up. Yoshi handed me a bath robe. I asked for another drink, since the alcohol had stopped working on me.
He handed me a beer and a shot of scotch, which I downed very quickly. We went out on the balcony of his flat and enjoyed the view of the city lights and the snakes of cars worming their way through it's belly.
I did feel much better after a few minutes and asked him to go back to bed.
This time I told him I just wanted to be on my back and he should fuck me in missionary position. Another condom and lots more of shower gel. He was very gentle when he pushed into me. Damn I got so hard, harder than ever before, or so it felt.
I loved when he pushed into me, felt loss when he pulled back, grabbing his ass to pull him further into me, frantically kissing each other. He became more urgent with thrust after thrust, feeling his hot breath on my face was driving me crazy.
After a while however I started to hurt more and more, until it became uncomfortable. I asked him if he could come soon, but he said we should maybe just finish off using our hands.
He pulled out of me very gently, but it still felt terrible when he did that, and we just got each other off with our hands while kissing.
He asked me how it was for me.
I told him it was the best sex I had ever had, and that was no lie.

Unfortunately Yoshi was just gay, He admitted that he had fun dressing up as a woman to seduce me, but had no interest in being a girl full time.
He has since moved back to the states and met a new partner he wants to marry.

[mabedzaqueen]

Originally Posted by badtube

I told him it was the best sex I had ever had, and that was no lie.

I enjoyed reading through this, badtube... A nice contrast when compared to other "first time stories" that may seem somewhat fairy-taleish... I believe all horny guys who think their first time will be a piece of cake or that "it's gonna work out like in the videos" should read your story!!

As for me, well i did cross to the other side 9 years ago (at the not-so-tender age of 46) and haven't really felt like coming back...
That said, whenever an unknown woman returns a smile (2 or 3 times a year) i tell myself ?maybe i shouldn't keep my door closed to them after all?

[badtube]

Thanks for the comment Mabedzaqueen,
sorry to hear your experience wasnt as good as mine.
I think we should just keep an open mind.

[siennagrace69]

I've been attracted to both sides nearly all my life, I just don't see the issue---Tgirl or man ?? I'm looking for the cock to satisfy my mouth and my ass !

[gretchen]

I am new here so please bear with me until I get more comfortable.

I love and respect Ladyboys , Transgenders pre-op. Crossdressers but not men. I do so love sucking cock and feeling the warm cum in my mouth. I love to be fucked with anysize cock as long as it's from one of the above beautiful people.

Love
Gretchen