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My 1st pleasurable gay anal sex experience

[image]If you don’t like reading about gay sex. Please move along. In this erotic story everyone was an adult and it was very consensual.
When I was 20 I started experimenting with my gay sexual experiences.
I had a much older friend with benefits. He was 45 and he loved playing with my body.
I would go to his apartment every Tuesday after work.
There was a particular Tuesday that made me learn how much of a sub or bottom I liked to be.
I rang his bell to get into the hallway to get to his apartment. As always he knew I was coming by. He buzzed me in he would leave his door cracked open so I could walk right in.
I walked in and he was sitting in his recliner with just a bathrobe on. He had a porn tape on with women getting anal sex. Which was my favorite.
I walked over sat down on his couch and we started talking . Then after he thought we talked enough. He would come over and sit next to me. He would have me lay down face up across his lap. Then he would start undressing me. Before I knew it I was completely naked and he would be playing with my body.
I loved being naked while he had his robe on . I felt so vulnerable and I loved the feeling of being his object of desire.
Once my cock would get hard. Which wouldn’t take long. He would start blowing me. I was watching the porn with different women getting fucked and I was getting extremely horny.
He stopped sucking my cock and led me to the floor in front of the TV.
He put some pillows down and had me lay face down on the floor watching the porn .
I was always interested in receiving anal but I was afraid of the pain.
Well, he had me face down and I was watching the porn wishing I was the woman getting fucked.
He started rubbing my back and I was getting relaxed as I was getting more excited. . He started rubbing down my back and started massaging my 20 year old ass. I loved it and moaned out loud. He would spread my checks apart to expose my little tight hole.
As soon as I was exposed I felt his tongue lick me. I loved having my ass licked. It sent jolts of electricity through my entire body.
I’m still watching the porn getting more and more excited.
All of a sudden I hear him pop open a tube of lube and then feel him spread it on my opening. It was cold and felt so good.
I found myself lifting my ass up in the air and then I could feel his finger start to penetrate me.
He was a big man , 6’4 with big hands. His finger felt a little rough but I was so horny. I let him finger me. He slid his finger in and I felt it go all the way in. Still was a little uncomfortable but I liked it too.
At this time I’m on my knees and he’s adding more lube and finger fucking my ass. Once I got used to 1 finger he added another.
I’m on my knees and watching woman getting fucked in the ass on all fours and I’m pretending I’m her.
I'm getting fucked harder and harder by two fingers then he reaches under and starts stroking my cock. OMG, I was in heaven.
He withdrew his finger and I could feel him squirt some more lube inside my wide open ass.
Now I feel his smooth cock head pressed in my opening. It felt so much nicer than his fingers. His cock was so smooth. He grabbed my hips and pulled me back onto his cock.
It took a few thrusts but he was all the way inside me. I could feel his cock rubbing my prostate. It was like I was having an orgasm with every pump without actually cumming.
I was the woman on TV getting fucked and I loved it.
I found myself pushing back against him and I was loving it. I was pushing back so hard and moaning while he was fucking me.
He let go of my hips and reached around to my hard cock. It felt so good getting a reach around as I was pushing back and letting him fuck me hard.
I was getting close to cumming butt I didn’t want to. I loved the feeling of getting fucked too much.
I told him to let go of my cock, grab my hips and fuck me hard.
OMG, his big hands on my hips and just pile driving my ass. I was moaning like the whore on TV.
I told him to grab my cock when he was going to cum.
All of a sudden he grabbed my cock and kept fucking me. I could feel him grow even harder then I could feel him shooting his load deep inside me. He would always shoot a big load butt this time it was in my virgin ass.
Something must of triggered me because now I was cumming while he was still fucking me.
Once I came I could feel his cock flop out of my ass. I could feel his load inside my ass and I loved it.
I got up and got dressed butt my whole body was still shaking. To this day 35 years later it is still probably my most powerful orgasm I’ve ever had.
I remember walking to my car and driving home and even walking into my house still shaking from my orgasm and excitement.
Topher1972 · 51-55, M
Nice! I haven’t had the real thing yet, just dildos but I know what you mean by a powerful orgasm.
Cantsayno · 56-60, M
@Topher1972 it’s incredible, leaves your whole body shaking
Topher1972 · 51-55, M
@Cantsayno I so look forward to to the day. Just have to meet the right guy. I’m picky of course and always safe
Cantsayno · 56-60, M
@Topher1972 me too. I’d love to find a FWB. To just have sex with.
Gillian30 · 61-69
I need to try this sometime 🤔
Snuffy1957 · 61-69, M
@Gillian30 @Cantsayno
Yesssssss 😋
Gillian30 · 61-69
@Cantsayno Sounding better and better . . .😜
Snuffy1957 · 61-69, M
@Gillian30
More than one is sooo much better😋
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samanthaX · 41-45, T
@Orpheus I love chatting naughty with you honey ❤️❤️❤️❤️❤️
samanthaX · 41-45, T
I have begun to dress as a woman whenever I have to wear clothes. I feel so good dressed femme and it feels so natural to me. I'm finding my desire for sexual intercourse has increased tremendously and I have made it known that I am sexually available to all my male friends ❤️❤️❤️❤️
Cantsayno · 56-60, M
@samanthaX I wish you all oils dress me as a sissy girl so we can go and have some fun !!!
CDPixie · 46-50, T
Omg. That was lovely. I love being cummed in.
Cantsayno · 56-60, M
@CDPixie I love your stories too !!!!
doodatt · 61-69, M
Thank you for sharing that experience. I’m hot and horny now.
Cantsayno · 56-60, M
@doodatt you’re welcome. Glad I could help !!!! 😂
doodatt · 61-69, M
@Cantsayno l wish you could
Cantsayno · 56-60, M
@doodatt Cum get me !!!!
Jacko1971 · 51-55, M
I wouldn't want to have unprotected anal sex with a man I didn't know very well but I would be curious to experience the throbbing of a big dick as it pulsates and shoots it's load deep inside me. That must be quite a sensation.
Jacko1971 · 51-55, M
@Snuffy1957 never say never
Cantsayno · 56-60, M
@Jacko1971 cum take a lick 👅
Jacko1971 · 51-55, M
@Cantsayno Next time I'm passing that way I'll be sure to stop by.
VisionQuest · 51-55, M
Being a bottom is am amazing experience! ❤️
SissySecrets · 41-45, T
An older man too. So sexy.
Ozdharma · 61-69, M
A fantastic experience for you so satisfying
Cantsayno · 56-60, M
@Ozdharma I’m so horny right now. I need someone to fuck me !!!!
Ozdharma · 61-69, M
@Cantsayno I would be happy to 😃
Cantsayno · 56-60, M
@Ozdharma cum and get me !!!!
Snuffy1957 · 61-69, M
I still love this story and it still makes my cock hard as a rock😋
Cantsayno · 56-60, M
@Snuffy1957 well, I know where that hard cock can go !!!! 😘😜
plasticpants02 · 61-69, M
@Snuffy1957 me too
PTCdresser57 · 61-69, M
What a wonderful experience
Cantsayno · 56-60, M
@PTCdresser57 It gave me the most powerful orgasm. I wish I had a male fuck friend now !!!!
PTCdresser57 · 61-69, M
Dont we all wish we had one Cantsayno
Cantsayno · 56-60, M
@PTCdresser57 I do. Times like this when I'm super horny. I wish we could have a Similar Worlds convention and get crazy !!!
Snuffy1957 · 61-69, M
That's HOT and gave Me a hardon😋
Cantsayno · 56-60, M
@Snuffy1957Well, I know where that hard on can go !!!!!
Snuffy1957 · 61-69, M
@Cantsayno
Well I can't say no to that 😋
plasticpants02 · 61-69, M
Well now that got me very horny, great story
That sounds awesome maybe one day I will do that
oldercanuck1 · 70-79, M
Very close to the same as my first time ,,, love it ,,
melbeacher · 56-60, M
Cantsayno · 56-60, M
@melbeacher Thank you. I wish I could relive those moments and do more.
oldercanuck1 · 70-79, M
it is so true the way it happens ,,,
Randie · 61-69, T
turbineman40 · 80-89, M
Amazing story
Gillian30 · 61-69
Wow Amazing 😯
Dacrowman · 70-79, M
AWESOME story 👍
Snuffy1957 · 61-69, M
This story still gives me such a hard-on 😋
Snuffy1957 · 61-69, M
@Cantsayno
Of course but your mouth is first... and last of course😋
Cantsayno · 56-60, M
@Snuffy1957 Promise ?????
Snuffy1957 · 61-69, M
@Cantsayno
Oh yeah😋
novaguy2u · 70-79, M
It sounds exciting and stimulating, so different to my first time.
Cantsayno · 56-60, M
@novaguy2u so it was t the first time. It was my first pleasurable time.
rango · 46-50, M
Cantsayno · 56-60, M
@rango thank you
rango · 46-50, M
Dacrowman · 70-79, M
Fabulous memory 😜
3Dogmatic · 46-50, M
Dacrowman · 70-79, M
At my local zoo they threw 2 penguins into the lion enclosure
But luckily they could unwrap them lolo
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turbineman40 · 80-89, M
@samanthaX I wonder if the reports your Mistress gets back from the parties you attend and provide all the sexual favors has something to do with it. Or more likely it's your desire to want to be done by two men at the same time and not Mistress's idea?
Topher1972 · 51-55, M
@samanthaX That is a big fantasy of mine
Cantsayno · 56-60, M
@samanthaX I would love that too
samanthaX · 41-45, T
You have a beautiful cock xxx samantha xxx
Cantsayno · 56-60, M
@samanthaX Thank you
samanthaX · 41-45, T
I have had it good but not as good as that ❤️❤️❤️
samanthaX · 41-45, T
Wow amazing xxx
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Cantsayno · 56-60, M
@samanthaX Not sure if I would want it permanently. But I would love to find out what a female orgasm feels like. I'll bet it's so intense. I would be such a whore !!!!
samanthaX · 41-45, T
@Cantsayno the more I have anal sex the more I crave it sir, I'm addicted xxxxx
Cantsayno · 56-60, M
@samanthaX I get it. When I had my suction cup dildo. I would ride it and cum. Although my ass was sore I was so turned on I wanted and did it again right after another

 
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