tagGay MaleSissy for Older Men Ch. 01

Sissy for Older Men Ch. 01


These experiences I'm writing about, are made from my former relations with older men ( being only with older men until now:) , only names and places are not the real ones.


I should start with the beginning into the world of older gay men, which was 10 years ago, when I was 19 years old. Until then, I've been only curious and had only fantasies about being with an older man, since I was a teenage boy. I remember seeing in the shelf of a newspaper store a gay magazine and I was so excited thinking about that, passed several times around the store, but realizing that it would be impossible to buy it, as I was too ashamed to ask for it.

So mainly, until the first time, my experiences were reduced to online sex chat with older gay men , without webcam as I didn't have one at the time, I had a small camera I use to transfer pictures in the PC. I learned then what older man wanted from younger men, I heard the most perverse requests from older men all over the world...One of them, a 60 year old bald man, was always asking me for pictures of my open ass, and then showed me on webcam as he coated them with his sperm. Problem was I didn't find anyone close to my home , or safe enough to try also a real meeting. For me it was flattering that older men found me very attractive, as they use to try all kind of tricks from money to paying plane tickets to visit them..I'm a 1,80m dark haired with athletic body as I practiced all kind of sports from basketball to swimming, and also I'm naturally hairless, at 29 now I still have very little hair on my body..this was very arousing for an older man as I observed...

To get to the main story , first time had unexpectedly happened during a short trip with my parents at the seaside. Here we have exit at the Black Sea, the beaches are very nice during the summer..And not only the beaches as I soon found out...

I was in my first year of university , but my parents said we should all go to a resort at the seaside, as they got some free tickets to a hotel, from the company they used to work with. I had my separate room anyway so I said ''What the hell...I'll hit the beaches and in the evening I'll go to local bars and for sure I can meet with some school friends''. So here I was happy in my room, watching the sea from the window, and changing rapidly from my clothes to the swimsuit, and then directly out of the room towards the elevator . Reaching the elevator, I noticed a bulky old man, sitting on the sofa in front of the elevator. He was around 60 years old, bald with traces of grey hair on the side of his head, big glasses, and showing a pretty large bear belly under his half open shirt. I took a quick look , my mind was at the beach, not on anything else and DING! the elevator arrived. I felt the older gent coming rapidly from behind me, so when I entered we were both in the doorway. He turned to me and pushed his belly on mine , and mumbled :

- Hey boy, watch it, I'm older than you!

- Sorry, sir I squeezed some excuses and let him first in the elevator.

- Young men this days, you're too in a hurry! , he said and gave me a bad look.

I said nothing , in that moment I just wanted to get out as quick as possible, thinking what grumpy old man I met. I felt his staring eyes on me, so when the door opened I just popped out. PFUUUUUU...at last , the beach, so I totally forgot about him, just went and got a sun chair for myself and flopped into the sea.

When I returned, I froze as the grumpy old man was sitting in the chair next to me..

- Hey again he said, sorry for the attitude back there, I hope you're not mad. My name it's George, and he offered me his hand, and a big smile.

- No problem I said , shaking it and looked to him. I'm Robert.

- So, in vacation with your friends I assume..huh , said George

- Actually with my parents, I said and thought for the moment ''I hope he won't start to tell me stories from the past as all older person do ''

- Yeaaah...vacations in the family, he said, I remembered when I use to come also in the 60's.

''Damn!'' I thought'' I was soooo right, here we go with the stories''

-But I wouldn't want to bother you with this, he said, and he leaned in the chair, opening wide his legs , revealing his hairy belly with strings of curly gray hair that was pushing from under his shorts like tentacles..

Me I started to oil myself with tan oil, sitting on the chair, and did this for a few minutes. When I turned towards him , I saw him staring strangely at me, and when realizing that I've seen him quickly turning his head. My heart started to beat rapidly, what if this is really happening, and he's interested in me, what if..and for the moment I was just gazing at him thinking of this.

- What?! I have something on myself? he said

- Nnn..noo no, I said, I was just facing away from the sun! stupid things to say as the sun was in my face now...

- C'mon Robert , why don't we take a beer , it's kind of hot , don't you think? I'm buying the first, as I was bad earlier, he laughed

- Ok, I said, and just followed him like a little puppy , thinking ''This is not happening!!'' I struggled with the flow of blood that rushed in my cock, so I won't embarrass myself.

And so we've chatted for a couple of hours about fishing, weather, school...He told me he was a retired music teacher, and the doctor advised him to come to the seaside for his back problems(a lie as I saw later on), and that he could use some company to play chess ..I was getting kind of bored, and also thinking maybe I should be careful as this man for sure it's not gay, I had misinterpreted in the beginning, he's just in need of chatting.

- So , I see the sun it's rising and burning , maybe we should go, he said.

- Yeah, I yawned it's too hot, and stretched myself...showing my muscles over the table.

- Good I see you do some sports, very good for health Robert, he laughed and started to get up from the chair. What do you say about a small chess game in my room? he said rapidly

- A..Aaaah...Mmmm ok, I said starting again to feel high.

We have entered the hotel, and I wanted to go to my room to change. Then he said with a authoritarian tone :

- You can do that later, the game it's more important, I don't have all day!

- Ok, I said swallowing my words, and entered his room.

The room was a little mess, towels everywhere, and clothes around the bed...the door closed with a loud CLANK! and he said

- Ok, now! You can sit on the bed, I'll get the chess game in a minute.

I was kind of dizzy from the beer , so I turned to him wanting to say that it's too messy, and found myself face to face with him, his belly almost touching mine, and his eyes were just wide open under those thick glasses..in the seconds that followed he grabbed my thighs and pulled me towards him, breathing heavily, and with a moan pressed his lips on my mouth. My first instinct was to get away, but he held me good :

- Stop...Robert..where do you want to go my dear!?..Mmmmm...you're sooo nice...I knew from the first moment you like me..and he started to lick my neck..

- N..nooo...stop I said! I'm not....but in the same time I felt my cock just getting rock hard, and a wave of heat invaded me..

- Ohhhh..yes you are! Yes you are...you're made for this he mumbled , and groaned, and in the same time ,just licking my face and leaving long slimy traces of spit on my face..He was shaking like almost a heart attack hit him , and I was like drugged just like a puppet in his hands.

He stopped suddenly his licking, and pushed me on the bed :

-Take your shorts off! he shouted, and in the same time struggled to release his cock from his shorts. I remember now after all those years, that image , this older man in blue shorts, shaking from excitement, and then, getting out not a monster as everyone would imagine in a fantasy, but a normal sized cock 6' at most, but thick as a large salami. It was fully erect, red to purple from the excitement, with one large vein going from the base to the head. I'm 7 and a half inches myself, so bigger, but his thickness surpassed twice mine.

I followed his orders and release my shorts, he just jumped on me, crushing me with his belly and rubbing his cock on my cock, and on my thighs.

-So nice , so nice you are! You're mine to have now, he almost cried.

I was a little scared by his reactions, it seems I was really a treat for him, cause he was over excited. He then, moved up, and before I realized his cock and hairy balls were just rubbing my face, he held his overinflated cock head , pressing my lips, his hairy sweaty ass on my chest and almost squealed :

-Open up, stupid! and pressed even harder, so I opened and just got my mouth stretched from the meaty organ. Almost a third of his average 6' was this thick mushroom head, feeling musky , and salty in my mouth. I started to lick it so I could breathe, but he pushed it in , moving it more inside...I choked, and started to cough..He just moved on his back, and without a word just pushed me from the back of the neck, towards his cock.

-C'mon, pretty boy! Be good with me, take it! And he just rolled his eyes , when I got the purple head in my mouth again. A large moan , just exited his mouth..as I tried to do as I saw in the porn movies, licking the head of the cock, with my tongue just following the crown, the taking it back in my mouth , soaking it with saliva...That was really exciting for me, and I felt that my cock is going to explode, I reached for it, and he saw this so he said:

- Stop, now jerk off in front of me , please!

So I got up and started to jerk my cock looking at him, trying to put a whore-face I saw in the movies, but I think it was just a funny face as he said :

- You like it .aaah? now turn around and bend over, show me your pussy-whole!

- It's more like a man whole no? I asked just bending over , revealing my hairless ass.

-Oh my God! What a superb pussy you have boy! he groaned.

I turned towards him again , as I felt I will cum, my face was all red...he quicly moved from the bed, seeing I'm close and took my cock in his hand, moment in which I just felt that the heavens are erupting, as in large volley spurts I cummed all over his belly and chest.

-Mmmmmm..excelent! You're a nice boy! You held this in you for a lot of time...I was almost fainting from the orgasm, but he quickly started to spread all the sperm on his body on my body ,and shivering dragged me to the bed.

- Come back and suck me again! he shouted

I returned in the bed and took his manhood in my mouth again, this time, licking it in long in-out moves:

-Ohh , yeah, ohhh yeah , he was grunting, you've done this before, you're so good at this!

I lifted my head and said : - Actually this is my first time...!

He just stopped moaning and lifted his head :- REALLY! I don't believe this!

-Really , believe me, I said. The scene was somehow comic, he just sitting on his back, me holding his cock in my hand and just looking at each other..

Then he said one thing that was the opposite of what I was expecting ( I was expecting some comfort words):

- I'm warning you doll face then, I haven't drained my balls in 3 weeks, have you tasted sperm before?

- No, I said, feeling his organ getting even more thick.

- Then it's bad...but you must learn, he laughed. Go on, I'm almost there!

So I restarted my blowjob, this time faster, in my mind thinking I'll feel when he will be close and get away. I wanted to taste the cock, but sperm I wasn't ready for it..

He started to moan and grunt more loudly, and he suddenly with a loud pop! removed his cock from my mouth leaving a long saliva string linked to it, and got on his feet holding his cock:

-Damn it! I want to hold it as much as possible, you make me cum too fast! he said holding his thick knob, that was abnormally red-purple...like the blood was getting close to burst out.

- Then you don't want to finish now? I said looking up to him...It's good cause I'm not really sure that I'd like to eat sp...

-Aaaaa...shut up, boy! he interrupted me , and just got closer to my face with his dick , grabbing me by the top of the head and trying to get his cock in my mouth. I opened submissively, and he started to move his cock in and out..What happened in the next seconds was hilarious and tragic in the same time , I just heard something like a squealing grunt, almost like a cry, and felt that the organ just compacted. He unleashed his seed so powerful that for an inexperienced man like me, the result was that the first spurt gone out my nose, as I was sucking in that moment, then immediately the next just filled my mouth , I tried to retry, but received a third glob of yellow thick sperm right on my forehead ,and going upwards in my hair from the force. The fourth one hit one mf my eyes closing it shut, and then the next three ones coated my cheeks and nose with sperm.

I was paralyzed , just stood there with sperm flowing from my nose and hair, down my chin hanging like ropes , one eye shut and feeling the strong taste in my mouth too. He just breathed heavily and I saw his knees shivering, he collapsed near me on the bed, and laughing.

I took a glimpse of myself on the mirror near the bed, and almost laughed myself. I was caught in a web --like sperm mask, with all this yellow spunk , smelling of old sperm, after boiling in the balls of this old man for 3 weeks.

-Wow, boy! This was fantastic, BRAVO! You really took the whole load!

-Please help me with a towel , I said, feeling after one on the bed.

-No, not yet, he took my hand, let me watch you for a moment..Perfect, I haven't cum this much since I don't remember when..

-Ok, but please, it stings!, I said as the cum started to dry off...He guided me to the bathroom saying, well it's good your parents don't have the room close to me. They wouldn't like seeing you getting out of here, after the sounds I did, and he laughed loudly.

I cleaned myself , up, and then just spent the next hour or so , discussing about gay sex. He told me he always liked the male ass and mouth, that he started as taking also lessons from an older person, and then since his 40's concentrated on fucking only younger men.


Of course the next discussions were about anal sex, but this in the next chapter, if you dear readers think I should go on with writing the rest .

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by Anonymous07/07/17

Older men

Since my teens I have always liked older men ( and women, but not as much )
My mum and I lived in a quiet suburb of Manchester and being a single parent she had to work ( she was a secretary in an Engineeringmore...

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