This Reader has his first Gay experience with a younger guy…

When I was 30, I had my first gay experience with a young man who just turned 18 meet him at a party in the neighborhood where all the females had already left. I was talking to the slim, tall young man with black hair and blue eyes and just a little peach fuzz on his upper lip, and I asked him if he wanted to walk to my house and chill out, so we did after talking awhile and smoking a couple of joints I lay down on the bed to watch TV, and he lay down beside me it was cool so I covered up and he did too. I was almost asleep when he said, “Why don’t you suck my dick?”

I said, “Fuck you, man,” thinking that he was joking.

However, he said, “No, really lifted the covers, and I saw his half-hard dick. It was way bigger than mine, and he wasn’t fully hard.

I said, “Damn, your dick is huge. How big is it?”

He grinned and said, “Eight and a half inches!”

I had always been attracted to young guys, but nobody knew it. Therefore, I said, “Are you serious?”\

“Yeah, get down there and suck it!”

My tiny little dick was rock hard, but I didn’t dare pull it out. I was too ashamed of my 4-inch dick. I told him I would try, but I never sucked dick before I put it in my mouth. I loved the taste and started sucking what I could fit in my mouth and jacking him off in my mouth. He said, “Don’t jack it—just use my mouth.”

I got a little more than halfway down he put his hands on my head and started pushing my head down soon he was hitting my throat. I was gagging, he started fucking my throat I just held my mouth open and tried to relax my throat. After a few minutes of pounding my throat, he told me to suck his balls and took his hands off my head. I caught my breath for a second and for some reason his feet catch my eye. I’ve always had a little foot fetish but never actually acted on it.

He had the sexiest feet I ever saw on a man. I slid down the bed, and as he was asking me what I was doing, I grabbed a foot and started sucking his big toe. I peeked up and saw him smiling. He knew I was his bitch now. I sucked all of his sweaty toes and then kissed back up to his big balls, licking them and sucking one in my mouth. He spread his legs wider then lifted them. He told me to lick his asshole. I licked from his big balls to his asshole spreading his cheeks. I slipped my tongue deep inside of his asshole, and I loved the manly taste. I had eaten women’s ass plenty of times, but he was much better even enjoyed the smell. I could tell he hadn’t had a shower since morning. It didn’t smell like poop. It had a smell that made me lick deep as I could. He was jacking his big cock.

Then he grabbed my hair, pulling me up. He said, suck it. I started sucking, and he shoved my face down. I felt him tense up, then a big string of hot cum hit my throat, gagging me. He still face-fucked me and filled my mouth. I heard him say, swallow it all, and I did every last drop, even licking up a big drop that dripped out my mouth. Looking at his eyes, I saw him smiling at me.

I lay down beside him, and after catching my breath, I started to undo my jeans, but he said, wait, let me do it. Grabbing my hand, he undid my jeans pulled down my pants and underwear. I saw him almost burst out laughing when he saw my tiny little dick. I was so embarrassed this teen boy was more than twice as long and thick as I am!

He started sucking it, telling me very sternly not to nut in his mouth. I knew he was the boss, so I said yes, sir. He only sucked a couple of minutes before telling me that I was too hairy and I would have to jack off. I did while he watched with a big grin on his face when I shot my little load.

Then after he rested, he said, “I wanna fuck your ass.”

I said, “OK, but I’ve never been fucked before.”

“Bend over; your ass is mine.”

So, of course, I did after getting him some Vaseline first. He stuck his huge teen dick in my punk-ass deep, grabbing my love handles firmly. It felt like his dick was tearing me apart. He fucked my ass hard, as I almost got sick from the pain. The more I moaned in pain, the harder he fucked my ass. My throat and asshole were sore for days, but it was the best pain ever.

While this reader reveals his secret life…

You probably know a guy like me, macho, intimidating, a bit scary sometimes. I may live across the street from you, but here’s the thing behind the closed blinds on the bright sunny day I’m normally dressed in my finest bra and panty set riding a suction-mounted dildo while watching Shemale porn! Yup, 100% sissy behind my manly act. I have a three-inch cock hard when I can get it up, which is rare these days. Unless something is in my ass and a mighty 1.2 inches long when limp, which is most of the time? So, where did it begin? The cross-dressing came first. I spent most of my teens trying to work out how to get hold of panties to wear instead of getting into girls’ panties. At 23, I was still a virgin, and sure I had enough interest from women; I just wasn’t that interested in having sex with them.
I’d gotten good at purchasing women’s clothing for myself under the pretense of buying for my girlfriend. No one, it would seem, suspected a good-looking macho guy like me would be a cross-dresser, let alone a Sissy. Back in those days, I used to ride motorcycles a lot, and one of my favorite pastimes was getting all dressed up, putting my leathers over the top, and going for a ride. One cold, wet evening, I was feeling excessively horny, and a five-minute fumble in a pair of panties wasn’t going to be enough. Tonight I was going to take the plunge and indulge in what I really needed, namely a cock attached to a girl with a heavy dose of humiliation.

I knew of Shemale escorts a few miles away, close enough to get to but hopefully not close enough to be seen. I got my girly stuff on under my leathers, made a tense and nervous phone call to her, and arranged to meet. Her house was large and completely detached from neighboring properties, so much so I rode past it a few times, as I couldn’t believe it was the right address. Finally, I parked discretely around the corner, walked to the front door, and pressed the bell!

A bloody big dog started barking, and I nearly ran for the hills. After some shouting from behind the door, it opened to reveal a tall, slim but slightly muscular lady, blonde hair, very long legs probably around 40yrs old, not beautiful but sexy if that makes sense. She beckoned me in and ushered me into the front room of the house, which, judging by the mirrors and double bed, was her working room. She was quite conservatively dressed, knee-length skirt and blouse, she asked me what I’d like, and the words croaked out, “I wanna be your bitch.”

A slight smile was the reply before she ordered me to strip.

Now, this was the bit I was looking forward to. I stripped off my jacket and top while she was getting something from the draw and when she turned around, I dropped my leather trousers! Her eyes widened in surprise as I presented my black hold-ups, tiny black satin shorts with matching spaghetti top with pink bra straps exposed.

“Well…” she managed to spit out after a moment, “What have we here?”

“A sissy bitch, miss,” I croaked.

She walked toward me and kissed me on the lips, then sat on the bed, ordered me to my knees, and instructed me to kiss her feet. I willfully lapped away until she instructed me to start working my way up her legs. I got to her knees, and she stood and told me to unzip her skirt and pull it down. As I did, I came face to face with her panty-covered crotch. Her panties were white satin with a significant bulge. “Kiss my panties,” she ordered.

I kissed and licked the silky material until the bulge had doubled in size. My own little cock was still safely tucked away, wasn’t even hard but was leaking precum heavily into my panties.

“Take my dick out,” she ordered. I pulled the panties to one side to reveal a big shaven cock. “Now suck!”

First time in my life, I had contact with a cock that was not mine, and it was in my mouth. I’d had no idea what I was doing, so I sort of sucked it like candy, licking best I could. She obviously got bored quickly as she ordered me onto the bed and handcuffed me to the bed frame. “Now, what’s in here?” she giggled as she unbuttoned my shorts and slid them down my legs.

My black lacy Panties were now on display, and there wasn’t the slightest bulge! She put her hand inside the leg hole and felt about, a wry smile spread across her face.

“What’s this little thing?” She giggled as she pulled my little limp, slimy cock out. “No wonder you don’t know what to do with a real one. You’ve never had one.” She laughed. She started wanking me until I was semi-hard. She looked me square in the eye and simply said, “Little bitch….”

That was it for me! I shot my load all over myself, covering myself in my own cum. She smiled and simply dipped he finger in my cum and rubbed it across my face. My humiliation was complete, I went back a few times, but that’s another story.

Another Reader is cuckolded in prison…

This is a true story about how I became a cuckold husband. My wife and I are both in our early 50’s, and she has a hot sexy body that I found out I love to watch her getting fucked by our neighbor. She has been fucking him for a while when we started talking about having a threesome. Well, it wasn’t long before he or I would be texting and trying to get her fucked or watch. All this went on for a few years, and then I got in trouble with the law. So two and a half years was all I had to do, and I made parole. When I got home, Renee and I had a lot of fucking to catch up on. So I asked her how many times did Lou try to fuck her?

She said how he was a perfect gentleman, and I knew right then he fucked her. She said she had called him up one night, and he invited her up to get high. She already knew if he got her at his house late at night, then that pussy was fucked. She had worn something thin and white, her favorite sundress, without anything under it, and when she said how she would love to watch her jack off if he needed some relief because of his girlfriend leaving him a couple of days ago.

She said he stood and let his shorts fall to the floor, and his cock looked huge. It is huge, and when I first watched him fuck her, I thought, damn, she got lucky with that big cock. I have a tiny cock, and she has told me repeatedly how he filled her up and when I got out of prison, I had forgotten just how much he does stretch her out, but that’s another story. Anyway, she said when he had all of his thick shaved cock out, she hardly even noticed.

I knew then he fucked the hell out of her. She knows that she has no reason to tell me anything other than the truth, and this was no different. I listened, and finally, I ask did she remember that I have watched the way she gets when we go to a party with him? I tell her that I want to hear all about how he tore her pussy up. She finally does, and she said he made her his little cock whore for the rest of my stay, and he used her holes as he wanted to. I said, well, I love sloppy seconds, and she was already texting him, telling him how she is craving his thick cock.

Yet this reader is exposed at the public pool…

I’m a gold member. One time when I was 18, a female friend of mine invited me over to hang out at her pool. The only other people there were two other girls she is friends with. I jumped from the diving board, and my swim trunks fell off. I was humiliated. The girls grabbed my trunks and told me if I wanted them back, I had to come out of the pool and get them without covering. My face turned bright red as I climbed out of the pool, my tiny erection sticking straight out for the pretty girls to see.

Naturally, all the girls started giggling like crazy. They were lying about giving me my trunks back and tossed them over the fence where I couldn’t get them. Since the water wasn’t cold, I couldn’t use shrinkage as an excuse. I was just frozen there, unmoving as these hot girls were laughing at my teeny-weeny.

The girl who invited me held her forefinger and thumb not very far apart and said, “It’s so small! What would you even do with that tiny little thing!”

The other girls joined in making comments and holding their forefinger and thumb not very far apart. One girl called me ‘pinky dick,’ which gave them the idea to compare my dick to their pinky fingers. Obviously, my dick was no match. They all took selfies with my dick, holding peace signs and winking while holding my dick in their other hand.

I still see her sometimes, and they’ve told lots of other girls about my size, so I’ll hear girls giggle whenever I go over to her house, and someone else is there.