First Gay Encounter

I would like to tell you a true story of my first gay encounter, I have been using dildos for the past 30 years and I often fantasised about having a real penis in my ass.
I have done many kinky things with my girlfriend, dildos in the ass, Strap on's and twice we had a threesome with bi women. We once had a threeway with a pre op tranny which was good but I couldn't get her hard.

As time went by our sexual encounters dropped off which I'm not happy with because I'm horny as all fuck, I've got to cum every day so I needed some action. My girl friend went on holiday to japan for two weeks and I thought fuck it I'm going to look in the local paper for a tranny with a working cock, Well I found a cross dresser with a 9 inch cock.

I booked the hotel room and he turned up about 10.30pm, He went into the bathroom when he arrived and got dressed in suspenders and stockings, The first thing he did was come out with this fucking huge cock and told me to start sucking, So I did, My first cock suck I was very nervous but after 5 minutes I started to deep throat his cock, I mean deep throat balls and all.

I sucked his cock in all positions, 69,on a chair,on the kitchen bench, he was laying on the bed and I was cock sucking like I was a man dying of thirst and trying to swallow all his pre cum. Which I did, but I think I went a bit over board, He started to moan and the moans got louder until he shot his cum into my mouth and that's when I thought fuck we haven't had anal. Fuck it, I got carried away, The next thing I did was to make him pay for his early ejaculation, I made him suck my cock forcing him to take the massive amounts of pre cum, I heard him gagging when I was on the vinegar stroke, and then I exploded with a bucket load of cum, he nearly choked on that load, That will teach him to cum to early.

This brings me to my next encounter with the same guy, This time was the same thing, Girlfriend was away and I had to play, I went to his place paid the $200 for his services, and we started, me giving oral sex him putting his tongue in my ass, Then he got out a dildo and fucked me with it for about 10 mins, That was good and now it was anal penetration time. He puts on the condom, Puts the lube on his penis and I assume the doggy position and I could feel the head of the penis trying to enter my tight ass, But he went soft, I coughed to make my ass hole expand but it was all in vane.

I thought fuck this, im paying $200 a visit, He should be paying me. That's when I asked him are you horny in the morning like really early, Yes he said, So I was back there with my $200 at 4am. I walked through the door and there he was, Big 9 inch erection, Yes I've hit the jackpot so I get completely naked and start sucking his massive cock, I deep throated the whole 9 inches and some, This is when he started inserting his tongue into my very clean shaven tight ass, he fucking loved it, pushing his tongue deeper and deeper into my hole.

Well after 30 mins of that it was time to don the condom on his sword, lube was applied, I assumed the doggy position, the head went in, That was all good then he started to insert more of his weapon and that's when it started to hurt,i said fuck it hurts and he stopped, Then I said fuck me harder don't stop.

I was lost in the moment and it was the horniest thing I have ever done, I was yelling at him to fuck me good and saying things like ''dam horse cock'' which he had but I think the tightness of my ass made him climax quicker, He started to pump faster and faster, I wrapped my feet around his hamstrings to pull him closer, The thrusting got even faster and I was cuming through my ass, Holy fuck what a sensation.

After 10 mins of fast pounding my ass he started the vinegar stroke and blew his load in the condom, I told him to blow over my face but never mind it was all good but I really needed to be fucked longer.