Old trannie gets a boys virginity

Oh dear I’ve been a bad, bad old trannie. I let a teenage boy seduce me.

I normally only go with guys over 30 at least. But this teenager contacted me on a dating site. I gave him the normal “Thanks but I’m in my 40’s you’re a bit on the young side for me” reply. However he kept contacting me on the site. He was very curious and quite sweet. I chatted with him online and he said that he would really love to meet me.

I told him if he wanted to meet me that he could find me at my local sex club. He said he couldn’t go there. After a deep thought I said it would be O.K to come round on the weekend but not to expect anything. Right on time on Saturday night he turned up. I had dressed rather conservatively that night not wanting to give him too many ideas. I opened the door and here was a very young man who must have only just turned 18.

Welcoming in I told him to sit down on the couch and got him a cup of coffee. Sitting down next to him with my legs tucked under me and my skirt covering my legs I had a close look at him. Only about 5.7” tall and very skinny. Short brown hair and clean shaven (probably only needed to shave once a week if he was lucky).

We chatted about this and that and soon got started talking about sex. I asked him honestly if he was a virgin and that it’s O.K if he was. He said “I’m still a virgin both ways” and I thought I would clarify it a bit. “Never fucked or been fucked?” he said “No”. “ How about oral sex?” He said he hadn’t done that either. Damn here was a real virgin. “Have you ever even kissed someone?” he said a couple of girls but it “didn’t seem right”. “So you like tgirls then ?” He replied that “for some reason I don’t’ really get turned on by men but something about trannies gets me going. He moved a bit closer to me and put his hand on my leg. He looked at me and asked “Is it all right if I kiss you?” After a little hesitation I told him O.K. He leaned over and gave me a somewhat awkward kiss. I told him to calm down a bit and told him to open his mouth slightly and not to rush things. I then gave him a nice long passionate kiss with just a hint of tongue. I felt his hand move along my thigh and k pushed it back a bit. He took my and moved it towards the front of his pants for me to rub his cock threw them. As I was rubbing the he unzipped and put his cock into my hand. We continued kissing while I started to give him a hand job. He pulled back from kissing and asked “Can you please suck me?”

By this time it was a case of “oh what the hell”. I got him to lie back on the couch and pulled his pants around his ankles and got my first good look of his cock. He may have been only a small guy but not his cock! A nice cut 8” absolutely rock hard. I got off the couch and got on my knees next to him and started my work licking and kissing the head of his cock. I put my lips fully around the head and rolled my tongue all around it. Then bam! He blew!Damn he had only lasted about 1 minute! I wasn’t expecting it that fast and the cum mostly flew down the back of my throat. I looked up in total surprise and he apologized for blowing so fast. I told him “That’s O.K sweetie it happens”. Then he said something really surprising. “Can we keep going?” I had forgotten how much energy teens have. Oh well I went back to working on his cock and it didn’t’ take long for him to get hard again. This time I squeezed the base of his cock putting pressure on so he wouldn’t come so fast. “You like this?” I asked looking up at him. He’s eyes where closed and I could see him biting his lip. He got himself a bit more composed and said “I love it thank you”. I continued to suck and lick up and down when he reached down and pulled up my head. “Can I fuck you?” he asked. Thinking about for a second or two I decided “well I’ve gone this far wit h him” I told him that we should go into the bedroom. I actually had to try and not laugh as I took his hand and he shuffled into the bedroom behind me with his pants still around his ankle.

Standing by the bed I took his shirt off. Oh he was so thin with a totally hairless chest. I would have to be careful I didn’t kill him ( I can get very energetic) I went and got the condoms and lube out of the draws next to the bed and put the condom on him and gently massaged the lube on it. I told him “O.K sweetie now you need to very gentle doing this at first” I then got on the bed and presented myself to him doggie style with my skirt over my waist. He got behind me and I could feel the head of cock against my ass. He kept trying to push inside me but couldn’t quite get the aim right. I reached round behind me and took hold of his cock. “Just stay still for a second sweetie I’ll help” and guided his cock onto my hole and pushed back on to it while telling him “that’s it just push forward a little” He finally got inside me and I took firm hold with my ass and to push myself back and forth on to his cock.. He put his hands around my waist and started to get the rhythm. It didn’t take long for him to get more excited and push harder and faster. “Come on baby fuck me” I told him for encouragement. “You sure you’re a virgin?” I could hear him breathing heavily. It really only took 4 minutes or so before he yelled “I cumming” and with one last thrust I heard him groan and shudder as he blew his load while still inside me.

I disengaged myself from him and sat on the side of the bed. Gave him a kiss and told him that he had very well for a first timer. I could see he was a bit embarrassed and he quickly got dressed and said “I have to go” and got out as quick as he could.

He gave me a “Thank you” message on the dating site but I never heard from him again. Well if nothing else at least I gave him a memory that will last (or haunt) him forever.

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Posted by toniparr
3 years ago    Views: 4,455
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DavidinWi...
retired
1 year ago
What a sizzlingly sexy account!!! What a lucky boy he was!
scooby999
retired
2 years ago
I do hope he grows up to be a tranny lover,so good to see youngsters enjoying tranny sex..
2 years ago
MMMMM i WISH i HAD YOU TO POP MY CHERRY
Beverlysm...
retired
2 years ago
wow have to change my panties
Bev erly
xo
Nove254
retired
3 years ago
sexy story i liked it alot
3 years ago
hot story.
Mike-cuck
retired
3 years ago
Very hot story. That poor boy will be hooked on trannies for the rest of his life now
Matt188
retired
3 years ago
Where were trannies like this when i was a 18?
3 years ago
"Old"? In your 40's? Now I feel old
3 years ago
I am so hard right now! Thanks!
3 years ago
I wouldn't mind an introductino to trannys like this!
quin058
retired
3 years ago
That was one lucky kid thanks