So this is about my first experience. I am sharing this but I am really not a good storyteller, please be kind. A little backstory I am hetro and never been attracted to men. But I have played with my ass since my teens in the 80’s, random stuff like the plunger, etc. no knowledge of what I was doing right or not. Always in secret from girlfriends and ex-wife.
For work, I was sent to Arkansas was supposed to be there for 2 days, fly in work, verify day 2 and fly out that night. But part didn’t arrive they were lost in shipping. So I was forced to stay for a week waiting on parts. Bored checking back into the main office and emails. There was a popular bar with ladies in skimpy outfits across from the hotel. So I was spending every night there drinking. Knowing full well nothing will happen with these girls they are there to flirt and earn tips. After the 5th day of waiting for parts and going to this remote office to pretend to work other than a few emails. I am truly bored and sexually frustrated from seeing the beautiful women every night in short skirts and revealing tops. Not to mention my liver is taking a beat this week as I can sleep so I am drinking 8 + Guinness beers every night.
So its Friday night and I have few already, bored surfing on phone. I think well I can go to the hotel and masturbate again. Maybe I’ll play with my ass. There drug store down the road, I can get some lube but to use as a dildo? Then the random thought how about I go on craigslist and search the casual section. I have done this before but never try to actually reach out. So in the W4M section after a few hours and a few more beers. I am fed up with the fake accounts. Being a bit tipsy like why not let’s look at M4M. So per my regular habit, I am sitting at the actual bar so I have to be discreet with people walking around and etc. Due to the pics that are posted. I getting aroused by the pics of men’s hard cocks. So I close the phone app and close my tab at the bar. Head back to the hotel, where I open my laptop and go back to the M4M section. I decided to post my own, stating in short not experienced directly and looking to have someone F me in my hotel. A good 30 minutes go by with no response so feeling a little defeated but eventually, I do get a response. We chat over email for a little while, he agrees to get condoms and lube and meet at my hotel room. At this point, I have only a pic of him and I am very nervous.
So I decided that since late at night and no one should knock on my hotel door. I get naked and when he knocks that is how I will answer the door. He arrives and is taken back a little that have answered my door this way. Invited him in and little chit chat. Begin by kissing, which truthfully I had even thought about all this. I guess I had in my head he come in, do me and leave. Start stroking each other, I am so nervous I can’t even get hard. So I asked if he will do me doggy style. We are the bed, I get on my knees, he lubes me up and slides on a condom.
Note his cock is not very big 5 inches or so and very slim. Much small then toys I play with.
But he slides his hard cock in my eagerly awaiting hole. That moment of penetration was great, the warmth of his cock and his head penetrating me.
We go this for a few minutes before he asks that I get on top. I oblige and ride him to completion.
We talk for a bit afterward before I craving a cigarette. We get dressed and head downstairs. Say our goodbyes.
Not a very exciting story but please keep in mind at this time I am 40 years old and never been with a man, never really even fantasized about it. Nowadays I occasionally get on squirt or grindr. I haven’t had any other experience but I do look, chat and daydream. I really just need to get up the nerve and go for it again. Find someone with a nice thick one. Doesn’t have to be long but definitely thick.
This story was originally published here
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