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First time with guy in over 10 years

Junior42

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May 15, 2011
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Just a short but true story from tonight. I am 33 years old, have not been with a guy in well over 10 years. I did a lot of sucking off two of my friends in high school and a short time after, but never did too much more then kissing and blowjobs. Unfortunately one friend moved away and the other passed away. Due to not being out and being in a line of work where I dont want to come out, I have done nothing since then. Until tonight.

So, a few days ago I posted on craigslist an ad saying that I was basically looking to service someone 18-25 (younger so we would not know each other) with a bj and looking for nothing in return. Got all kinds of replies from people much older, a few people claiming to be straight but I wasnt good looking enough to suck there dick (lol) Oh well. Im a lil on the heavy side I know, but a BJ is just that. Anyway, got to chatting with this kid about 30 minutes away who was 18 years old with a girlfriend who said that he has gotten head a few times from her but that she can not deep throat, and he wants to see if it is better from a guy. I was thinking perfect. So we literally send 30 emails back and forth on a time to meet and then at the end it all fell apart due to my work schedule. I asked if we could reschedule for the next night and he informed me he spends 2 nights with his gf, then one back at his place and repeats that over and over so our days would not work for a bit.

I felt frustrated, and downloaded grindr to my phone. I had never looked at the Ap before and could not believe that even in the northeast how many people there were close by. Kind of played around on it, talked to some people, kinda creeped out a bit, but then I got a message from a guy Ill call Ricky. 22 years old, 6 foot 1, cute face pic in his profile and immediately sent a dick pic.

Convo was as follows

Ricky-Hey (photo then followed)
Me-Hey there, nice man
Ricky-Want it?
Me-Yeah, would not mind giving that a good sucking.
Ricky-Im free now and can host but need to work later.
Me-I need to work too, maybe another time.
Ricky-I have tomorrow off
Me-Same here

Convo was much longer, but thats the point. I also admitted to him that I had not had any contact with guys in a long time, that I was overweight but just looking for him to come in, give head and then leave. He said he was fine with that.

The next day I chatted him up again. I asked what he was up to, and he said he was hanging out with some friends. I figured that was a nice way of saying so leave me along, but a few seconds later he responded with "but i drove here alone" I figured that was my window, and told him well if you want to stop by for head on the way home you can. After seeing how late I would be up and me telling him that I wanted nothing in return, just come in strip down, get off and go he said "Nice dude, Ill definitely stop by"

About an hour later he messaged me saying he was on his way and it was odd and funny as the ap showed him getting closer and closer until the headlights of his car was pulling into my driveway. I greeted him at the door all nervous having never done anything with a stranger before, just friends. I invited him to just sit back on the couch, placed a pillow down on my wood floors for comfort and got in front of him. He took off his shorts revealing no boxers and kicked them away.

It was like riding a bike, I just jumped right on to his soft cock, putting it in my mouth and started working it. He started unbuttoning his shirt button by button and threw that to the side. I saw that as permission for my hands to start wandering to his back, under his ass, and playing with his nipples. His cock was getting harder by the second to the point it was stretching my mouth pretty good. I just kept going slow, and then a bit faster while rubbing his stomach.

I went down and took one of his nuts in my mouth, and then the other. he draped his legs over my shoulders. After a bit of this, I went back for his cock. I started going all the way down to the base and he was moaning with pleasure. Hearing him moan made it hotter for me. I sucked just the head a bit and then dove down full length again, he squirmed and was clear he was ready to blow. I took his cock from my mouth and jerked him as he shot ropes of cum on his cock, down my couch and on to the floor. As soon as he was done shooting I dove back down on his cock taking some of the cum down my throat and making him shiver in pleasure. He asked me to stop saying that it was too sensitive. As he was putting his shirt back on I just lightly jacked his cock and then released. He put on the rest of his clothes, said thanks, and took off.

I forgot how much fun it was playing with friends when I was younger. I messaged him after he left saying he was free to stop here anytime, and I hope he takes me up on that offer. I just need a friend or two to play around with. I messaged the 18 year old telling him I practised deep throating tonight just for him. Hopefully he will be up in the next week or so. It was an experience tonight that lasted about 10-15 minutes, but it was a blast.
 
happy to hear that you had fun. It's been 20 years for me. The last guy was a college roommate.
 
I was nervous. Im hoping he will message me sometime soon asking to come back so I dont need to go to him and ask him to come back :-)
 
Junior42,

If you do meet up with the 18 year old, please give us a full report! :D

Thanks
 
Thanks, will do. I got a message from him today wanting to meet today or Sunday before I work, but I asked him to pick a day I dont work so we are working that out still. Hope to have an update sometime soon.
 
Yesterday I was hanging out at the house around 5 in the afternoon and I get a message from "Ricky" asking if I was available. I said I had the day off, when was he thinking, and I got the response ASAP. Apparently he enjoyed our first meeting :-) I told him to give me 20 minutes and stop over.

He pulled up into the yard, came inside and went right to the same spot on the couch I asked him to sit in the first time. He had on loose fitting basketball shorts that just slid right off to the ground with no boxers underneath and another button up shirt. He sat back and I dropped down between his legs and put his soft cock into my mouth. Within seconds it began coming to life as I worked my way up and down in a slow rhythm. He took his shirt off and was playing with his nipples as I played with his nuts while I sucked his cock. He would put one leg over my shoulder for a bit then take it down and then do the other, giving me more access to his balls and cock. I tried going slower because he did not last too long the first time but he started using his hands to guide my head indicating he wanted me to go faster again. After a few more minutes he whimpered that he was going to cum. Remembering the mess he made on my couch the last time I decided I was not letting that happen this time and instead of taking his dick out and jerking him off I increased suction and did not let up. Before he could react he was shooting his load down my throat. I did not miss out on a drop as I gulped it down and then let his cock fall from my mouth. He looked spent as he began buttoning his shirt back up to leave. As he left I messaged him "see you tomorrow"? He did not respond but time will tell.

The 18 year old I had been emailing, I did a little facebook searching and found pictures with him and his gf. He is a tall kid, red hair, athletic body. He said he will be up Wednesday night around 10. After seeing his pictures, I sure hope so.
 
There has been a welcome increase in the number of these "true life" posts lately. They are a lot of fun to read, especially when they are as well-written as this one. Thanks for sharing this!!!!
 
There has been a welcome increase in the number of these "true life" posts lately. They are a lot of fun to read, especially when they are as well-written as this one. Thanks for sharing this!!!!
I couldn't agree more. True life experiences are much hotter to me than fiction, and these are very well written, indeed!
 
Thanks guys, appreciate that. Also, the 18 year old mentioned did show up and it another story I have written on here entitled 18 years olds not so perfect first time. However, 2nd time was pretty great. Its all in that story and all true.
 
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