Picked up by a Man

I nervously sipped my first beer in the Gladstone Hotel Tavern in Toronto. I was visiting relatives with my parents and needed to get away on my own for a while. I was very nervous because the legal drinking age in Canada at the time was twenty-one years old and I had barely just turned eighteen, which was the legal age in my State of New York. Also, at that time in Canada, Taverns had a 'Men Only' side and a 'Couples' side. You could only enter the couple's side if you were accompanied by a female. I, of course, being alone, sat on the Men Only side. After a few draughts and no one asking for proof of age, I started to relax and took in my surroundings.

After speaking back and forth to the guy at the next table, he asked if he could join me. He said that his name was Rick and I told him that I was Jim, from New York and was just visiting relatives in Canada. Rick was a very good-looking guy and I found him very easy to talk to. The place was crowded and noisy, so we had to lean close to each other to be heard. I could really smell his manly cologne as he spoke to me with his lips lightly touching my ear. His jean-covered thigh also accidentally kept rubbing against mine. Strangely, my eighteen-year-old cock started to get hard!

I had hardly any real sexual experience with girls let alone guys, so it never occurred to me that Rick was trying to pick me up. After all, this was a Tavern in a fairly rough part of town and Rick looked like he could handle himself. My misguided impressions at that time were that gay guys all had to be effeminate. I can't deny that being this close to Rick was turning me on though.

We traded off buying rounds when Rick suggested that we go to his place, which he said was near here, and we wouldn't have to pay for the beer as he had lots in the fridge at home.

As we drove a couple of blocks, Rick told me that his roommate Don was a bit of a sissy but was harmless. I started to get suspicious that maybe they were both gay. Strangely, instead of turning me off, this thought made me horny and hope that I was about to be seduced by men.

I loved to look at naked pictures of women, but I admit to having had a few jerkoff sessions where I fantasized about sucking a man's cock, especially while dressed in panties. Of course, I never thought that it would actually happen but now my heart raced as I thought that I just might have my first gay sex with two men.

I was an eighteen-year-old, slim, five-foot-seven young man with a six-inch uncut, slim, smooth cock that seemed to be perpetually hard. I'd always thought that my ass looked very girly and in fact, playing with my beautiful ass was always a part of my frequent jerkoff sessions. If I had any sisters, I knew that I'd be wearing their panties and bras when I jacked off. There was no online shopping in those days to be able to buy lingerie anonymously.

As I entered Rick's spacious apartment, he introduced me to Don, his very effeminate acting roommate. While Rick was muscular and over six feet tall, Don was slim and slightly taller than me, wearing corduroy men's pants and a man's shirt. Although I was slightly disappointed that Don wasn't dressed girly as I was hoping, I still felt my cock twitch as I watched his cute ass swish over to the fridge to get us beer.

"So, are you guys gay?" I asked, emboldened by the amount of beer that I had consumed.

"Yes, we are, but we're not currently lovers. We're sometimes roommates with benefits, and often even share men that we pick up." Don chuckled, with a slight lisp.

"How about you Jim, I saw you looking at Don's ass as he got us our beer, and I detected a cute little tent in your pants?" Rick said with a smirk, as my face turned beet red at the thought that other men had noticed that I got a hardon while looking at another man's ass.

I decided to hell with it and told them that I think that I'm straight but the thought of having sex with them is turning me on so much. I asked Don if he ever dressed girly and that I thought his long legs would look so sexy in nylon stockings and his pert ass was made for panties

"Of course I dress, darling, would you like to get dressed up with me? I sense a submissive side to you and your face is very cute and pretty rather than handsome. Oh, honey, we could be such sexy-looking sluts together!" Don lisped.

"That's why I picked Jim up, Don. He was so fucking cute and his ass in those tight corduroy pants looked as great as yours. You should have seen him trying to hide his hardon while I breathed into his ear and purposely rubbed my thigh against his. I'll bet I could have pulled my cock out in that crowded Tavern, put it against Jim's face, and he would have blown me in front of everyone." Rick laughed, as my face burned red with embarrassment again.

This was moving way too fast! I looked over at Rick, sitting in his oversized leather chair. He had his pants down to his knees and his large cock was tenting his pink panties. Wait, what? Manly looking tough guy Rick was in panties! That made up my mind right then and there to just go with what feels good and to hell with labels. I was going to try to fulfill all my fantasies!

I quickly stripped off my clothes and minced over to Rick with my hard cock sticking out in front and sat on his lap. The exquisite feel of his panties on my bare ass had my hard six-inch cock dripping precum. "Does this answer your question, sweetie? I'd love to dress up girly with you, honey," I said to Don, using a sissy voice. I wrapped my arms around Rick's neck and for the first time kissed a man. Rick kissed me back, inserting his tongue into my mouth as his now bare cock pressed against my ass and his hand grasped mine and placed it on his hard cock.

I felt a wetness on my cock as Don, who was now also naked, knelt and engulfed my rock-hard cock in his mouth, deep throating my smooth cock all the way to my cum filled balls while reaching up and pinching my erect little nipples.

I couldn't believe that I was actually naked, sitting in a naked man's lap with his hard cock in my hand, kissing and moaning with his tongue in my mouth while ANOTHER naked man had my hard cock in his mouth. This was just so erotic and at the same time forbidden and unacceptable in the world that I grew up in. I felt like such a sissy slut, but was loving it all and wanting much more!

I was afraid that if I had cum, the guilt would take over before I got to try out all the things that seemed so exciting when I was super horny but fizzle out once I cum. I thought that I may never get this chance again so I was going for it all and I hadn't even had one of these delicious-looking cocks in my mouth yet.

I reluctantly ended the kiss and slid off Rick's lap wanting to get a close-up look at these gorgeous men's beautiful cocks. Wow, I can't believe that I actually thought of men as gorgeous and their cocks as beautiful, but I felt so feminine, horny, and submissive at that point. I felt as if my whole life revolved around these men's cocks, balls, asses, nipples, and mouths. I needed to see their cocks and balls up close. I'd never really ever seen another man's cock at this point in my life. Mainstream skin magazines in those days only had pictures of naked women. This was even before Playgirl magazine came out, which was supposed to be a skin magazine for women but was mostly bought by gay and curious men.

I knelt as Rick and Don stood in front of me with their hard cocks pointing straight at my hungry mouth. Don's uncut cock, strangely enough, looked exactly like mine, around six inches, smooth and slim. I had always wished that I could suck my own sexy cock when I jerked off so it was going to be such a treat to pleasure a cock that looks exactly like mine.

Next, I turned my gaze to Rick's cut eight-inch cock. Whereas Don and my cocks' were a fair length and slim, Rick's cock was thick and manly, almost angry looking with thick veins. I couldn't wait to get these beauties in my mouth and maybe up my cute, smooth ass.

As much as I loved looking at and examining these men's cocks closely, it was now time that I tasted cock for the first time. I took both cocks in my hands and put the heads together, lapping the delicious precum off their cockheads. The taste of the two cocks, wet with sweet, salty precum caused me to instantly become a cock crazed slut. I stuck my face under their balls, smelling, licking, and sucking every inch of musky flesh that my lips and tongue could reach.

I had been taking turns sucking both cocks as far into my mouth as I could while playing with each man's ass with my hands. Loving the feel of these men's asses, I couldn't resist scooting around behind them and licking the manly ass of Rick and then the smooth girly ass of Don. I licked and kissed both men's asses and ran my tongue up and down their cracks, pausing to stick my tongue into their holes.

I had to get back to their cocks and sweet-tasting precum. As I again took turns sucking their cocks and playing with their balls, they began kissing and feeling each other up. With my mouth filled with cock, I could hear them calling me a Cock sucking, asslicking, faggot for men, which turned me on even more, if that was possible.

I momentarily took their cocks out of my mouth to beg them to please give me their delicious cum! I knew that they were both close to coming so I removed the cocks from my mouth and rested just the heads on my tongue. At the same time, I stuck two fingers up both their asses which caused their cocks to explode delicious, thick, creamy man cum into my mouth.

Delicious, creamy cum was flooding my mouth. Even though I swallowed as fast as I could, I thought that I was going to drown because their cocks just kept shooting. I just loved sucking cock and swallowing cum and knew that regardless of what the future held for me, I'd always be a secret sissy cocksucker. I would, at the very least, have to have an occasional cock or cocks to suck in order to get my fix of creamy man spunk.

As I suckled their cocks and licked their balls to get every last drop of cum, Don struck a sissy pose with one hand on his hip and the other palm down and stated, "Darling, you are going to be such a great sissy cocksucker. What you lack in technique, you more than makeup in enthusiasm. I've been gay and having sex with men for most of my life and you rank right up there with the best, and it's only your first time."

Rick came over to me, put his arm around me, and kissed me. His tongue searched my mouth for any leftover traces of cum, while his hand played with my still hard and unfulfilled cock. I asked Rick to not make me cum as I haven't finished doing everything that I wanted to do while I had that sexual high that comes from being so horny and uninhibited.

"All right then," said Rick, "I'm going to have a piss and take a shower."

"Oh, please baby, can I hold and aim your cock while you piss. I've always wondered what that would be like to have a big heavy cock like yours in my hand when I'm pissing." I pleaded.

Rick took me by the hand as if I was a little girl and led me to the bathroom. He stepped up to the toilet and I got behind him, reached around him, and grasped his thick, veiny eight-inch cock. As he started pissing, I moved his heavy cock around the toilet with one hand and used my other cupped hand to place into his stream. Once I had enough piss in my cupped hand, I brought my hand to my mouth and for another first, slurped and licked another man's piss off my hand. It was warm and salty and turned me on because it seemed such a taboo act for one man to do to another man.

My hard cock, meanwhile, had been rubbing against Rick's manly ass and found itself nudging his asshole. This caused Rick's cock to harden again in my hand and the piss stopped flowing. I moved around to his side and dropped to my knees and took his piss dripping cock into my mouth and licked and sucked any remaining piss from his beautiful hard cock.

"Jim, you have to be the biggest natural cumslut I've had in a long time," said Rick, as I continued to suck his cock and play with his balls and ass.

I took Rick's cock out of my mouth and said, "Thanks darling, I just can't get enough. I feel like I could go outside and sit on the curb and suck every man's cock that walks by. Oh yummy, what a delicious thought! By the way, where did Don go?"

"Don is in his room getting himself all dolled up for you, sweetie. By the way, when he's dressed, he refers to himself as Dawn. I know, it sounds exactly the same but that's how he wants people to think of him while he's dressed." said Rick with a chuckle. "When he's finished, he'll make you over as well."

"Oh goody, I can't wait to get into panties and other girly clothes, but I'm afraid that as soon as I pull on my panties, my cock will spurt and I'll want to go back to being straight," I pouted, batting my eyelashes like a sissy.

"Sweetie, anyone who takes to men as fast as you have, sucking their cocks, licking their asses, and drinking their piss while speaking like a sissy, shouldn't really have to worry too much about losing his lust for men." laughed Rick.

I also laughed; it did seem ridiculous that after the homo acts that I'd performed on these men that I would be so ashamed that I would all of a sudden quit wanting cock anymore. I knew now that even if I went back to relationships with women, I'd still need yummy cock in my life.

"You're right baby, let's get in the shower and you can put your delicious cock up my sissy ass and fuck the cum right out of me. Please, call me Dani while I'm being a sissy slut", I giggled, as I struck a sissy pose and fluttered my eyelashes again.

Rick turned on the water and handed me a small bottle and told me to rub it all over my body to remove all the hair, although I hardly had any anyway. While I tingled with the hair remover, Rick and I made out like teenagers, and I couldn't wait to have his big cock up my ass. His wet hairy chest and pink nipples looked so inviting that I bent down and started licking and sucking his nipples. Sucking a man's nipples felt so submissive and exciting. When we were washed and rinsed, I couldn't resist falling to my knees and again taking Rick's cock in my mouth and sucking it. I also couldn't resist turning him around and worshipping his squeaky-clean ass. I was such a fucking cockslut!

After Rick pried my face out of his manly ass, he stood me up and bent me over with my hands against the shower wall, like I was on an episode of Cops. He slathered lube on my hungry asshole, and I assumed his big cock also. I felt the big cock rubbing over my cheeks and cleft, searching for my hole. When he had it lined up with my asshole he started to gently push it in. Although Rick was very gentle it hurt like hell!

"Please Rick, take it out, it's too big!" I screamed.

"It'll soon feel good sweety, all the pain will disappear, and you'll wonder how you could have ever cum without a cock in your ass," said Rick as he gently eased more cock up my ass.

Just as Rick said, the pain had soon eased, and I started to feel pleasure as his big cock started a rhythm of in and out movements into my ass. Oh my God, getting fucked in the ass felt so good! Rick leaned on my back and nuzzled my neck and ears with his tongue and lips calling me his sweet little girly boi. When I heard him say that, I exploded my cum all over the wall of the shower. Each cumshot caused my ass to spasm, milking Rick's cock with my ass, causing him to shoot shot after shot of sperm up my sissy ass.

As I was catching my breath from the most amazing orgasm of my young life, I heard the sound of someone clapping. I glanced out of the shower, with the water still cascading over us, and saw a beautiful woman watching us and clapping. My God, it was Don, or rather Dawn! She had watched as another man fucked my ass. She had heard all my girly moaning and pleading to be fucked harder.

"Congratulations honey, you are now a full-fledged cock slut. You've had a man's cock up your ass and had him fuck you until he spurted up your ass. You've been bred by a man and forevermore will remember what it was like to get ass fucked!" exclaimed Dawn. He, oops, I mean she, looked beautiful and so sexy completely made up and dressed.

"Oh darling, you look so glamourous!" I exclaimed in my new sissy voice, "my sissy name is Dani by the way. You're so right Dawn honey, I feel like such a sissy. I don't want to look like or be a woman, I want to be a sissy for men and other sissies. I want to dress and wear makeup so that men will know that I'm a sissy who will instantly drop to my knees and suck their cocks or bend over and give them my ass. Speaking of which, I just came and there's no guilt, only a yearning for more cock," I said, as Rick and I dried each other off.

"My God Dani, quit playing with Rick's cock." Dawn chuckled. "We have to get you gurlied up so you can see your full sissy self. Also, you had better phone your parents and tell them that you'll be staying with friends for a few days. We're going to get you all the juicy cock that you can handle dear." Dawn said as she moved over and kissed me with her ruby red lips.

As we broke away from the kiss, I looked Dawn over from head to toe. She was wearing a platinum blond wig with shoulder-length hair. Her eyes were made up with blue mascara and thick lashes and her full lips were coated with shiny, ruby red lipstick. Dawn noticed that I was taking stock of her and started posing. She had on a red lacey satin bra accompanied by matching red lacey satin panties. There was a cute bulge in the panties that made me want to drop to my knees and lick her cock through the pretty panties. Sheer, red nylon thigh-high stockings, held up by a black lacey garter belt, completed her outfit. In her hand, she carried black stiletto pumps.

"Dani, sweetie, wait until you see what I have laid out for you to wear tonight. The other gurls will be so jealous." Dawn said, grabbing me by my hard cock and leading me to her bedroom to start my cross-dressed sissy life.

The other gurls? What fucking other gurls? I thought.