crossdressers

#2: Another Story



I met him at a drag queen bar called Tranz. Mind you, this was not a bar I would normally have frequented, but I had just gone through a very nasty divorce from my wife of 13 years Melissa, partly becase she discovered my attraction to drag queens, crossdressers, transsexuals, whatever you wish to call them and, believe me, she used that against me in the divorce. To add insult to injury, she informed all of our friends and even family members of my attraction and I lost a number of my friends and became estranged from a number of my family members as a result. So I figured I may as well indulge my fantasy since my “secret” was out.



And that was what led me to Tranz.



He told me his name was Tommy but that he also went by his other name of Tamara when he dressed up. This night he was wearing a black mesh shirt and a pair of black leather pants that were pulled down enough to expose his bright pink g-string. There were purple streaks in his jet-black hair and his was skin was pale white and he was rail-thin. There was ruby-red lipstick painted thick around his lips and dark blue mascara painted just as thick around his eyes and was also wearing blush. He didn’t come right out and tell me, but I guessed his age either in his late-teens or early-twenties.



And he was just about the sexiest thing I ever laid eyes on!



After buying him a drink at the bar and engaging in the usual chit chat for a moment or so, Tommy just came right out and asked me if I wanted to go back to his place. After being stunned into silence for a brief moment, I caught myself and managed to stutter out, “S-sure. We can do that . . . if you want.”



Tommy nodded as he slurped down the rest of his drink and then asked as he started walking past me, “Good, let’s go.”



I finished my own drink, laid down some money on the bar and followed him out. As I stood behind him, he asked without looking back at me, “You got a car or do we need to catch a cab?”



Again, I sputtered, “I . . brought my own car.”



He nodded again and held his hand out in front of him, “After you.”



I nodded as I stepped past him and he followed. We got in my car and he gave me directions to his place, which turned out to be a tiny two-room apartment, including the smallest bathroom I’d ever seen in someone’s place. There was a dirty mattress on the floor and that was about it. There wasn’t even a TV in the room. I figured Tommy didn’t spend much time in his place or there would’ve been more stuff. Of course, how much stuff he had in his apartment wasn’t my main concern at this point.



Tommy strutted his petite little ass over to his mattress and, after throwing his purse on the floor next to it, plopped down. I stood where I was finding myself unable to move. Tommy must’ve sensed my apprehension because he gave me this come-hither stare and patted the empty spot on the mattress next to him and said, “Come over here. Sit down. I won’t bite.” A sneer escaped the corner of his mouth as he added, “Not unless you want me to.”



I gave him a nervous grin and slowly sat down next to him. I wasn’t sure what to do at this point, seeing as how this was my first time with a drag queen and all, so I just started rambling on about, well, nothing. Tommy just sat there for a moment listening to me rambling on before he seductively placed his hand on my shoulder and cooed, “Relax.”



I shook my head in embarrassment and said, “I’m sorry. This is just . . . my first time.”



“Yes,” he said, grinning, “I know.”



I was about to ask him how he knew, but I figured it was obvious as hell. I did, however, ask why he picked me to go home with him in the bar. Before he answered, he reached into his purse and fired up the first of many cigarettes and, after exhaling a smoke-filled breath, told me in a very blunt manner, “Because I like fucking older men.”



I gave another nervous grin and sputtered, “Oh . . . okay.”



Before I was even aware of what was going on, Tommy grabbed my hand and placed it right square on his crotch which already had a noticeable bulge. After rubbing on his expanding crotch for I don’t know how long, Tommy unzipped his pants and pulled down his pants but not his flimsy hot pink thong that was stretching beyond its compacity. My mouth started salivating at the glorious sight of his growing erection that kept stretching his thong. He pulled his thong down and his cock popped out in plain view. Surrounded by a thick lush patch of jet-black pubic hair, his dick must have been a good eight or nine inches long. It was thin and veiny with a large flushed purple head that kind of matched the purple streaks in his hair. His balls were big and full and hung down as low as a man’s twice his age.



And it was the most beautiful thing I’d ever laid eyes on!



“You wanna make good use of this, don’t you?” Tommy cooed again.



I did. I didn’t have to say a response as I lowered my head and grabbed his cock at its base. I opened my lips wide and took at least half the length of him inside my mouth. I gently closed my mouth around his cock and started bobbing my head up and down on his erect penis, being careful not to scrape my teeth on the sensitive veiny skin of his luscious cock. I briefly took my mouth off his prick and licked on his jet-black pubes and pulled on them a little with my teeth. I took him back into my mouth and resumed sucking him off. This was my very first time tasting another man like this, and, I must say, it tasted great!



Tommy started slowly thrusting himself deeper into my mouth, causing the bulbous head to tap against the back of my throat. I thought this would make me gag, but, to my surprise, it didn’t. In fact, it was a rather pleasant senation even when he began thrusting faster. But, before he could come, he abruptly took himself out of my mouth and quickly reached for the zipper of my trousers. He took out my own erect cock and started to stroke it. My cock, admittedly, wasn’t as long as Tommy’s, but it was thicker and my balls hung down about as low. He wasted no time sticking it his mouth and started sucking on it gingerly. Now I could count on one hand on maybe two or three fingers how many blowjobs my prudish wife gave to me during our 13 years of rotten marriage. But here was this kid sucking my dick like there was no tomorrow!



Keeping his hand wrapped tightly around my shaft, he sucked my balls in his eager mouth and scraped them with his teeth. I threw back my head and moaned in both pleasure and a little pain as he both sucked and bit into my tender scrotum. He plopped my dick back into his mouth and began sucking on it again until I was on the verge of coming. I guess he sensed how close I was to orgasm as he abruptly took his mouth away from my throbbing aching cock and quickly pulled his leather pants and thong all the way off.



Without him saying a word or telling me what to do, I grabbed his legs behind his knees and pulled his legs back all the way up to his head and stuck my tongue as far as I could into his tight asshole. I licked around his bittersweet anus and then ran my tongue up the space between his asshole and his balls and sucked his ballsack into my mouth like he did with mine. I pulled on his nuts and ran my tongue around each of them as they were in my mouth. I licked my tongue back down the space below his nutsack and back down to his puckered asshole. I placed both my hands on his skinny ass and pushed my tongue back into his ass as deep as it would go. I darted my tongue in and out of his asshole as if it was my cock. After tongue-fucking him for what seemed like the longest time, Tommy abruptly grabbed my thinning hair and yanked my head up. He kissed me with surprising passion on my tainted lips before pulling his face away and telling me in a seductive half-whisper, “Now I want you to fuck me with that big cock of yours!”



Again, without me having to say a word to him, he grabbed my shoulders and pushed me down on the mattress. He positioned his ass above my cock which he grabbed and aimed it at his waiting asshole. He began to slowly insert my dick into his rectum and pushed himself down inch-by-inch until his ass was touching my waist. He leaned forward and put his hands on the mattress on either side of me and started to furiously fuck himself on my cock. I swear, I thought I was going to tear him in half he was so thin!



Keep in mind I hadn’t had sex in the longest time even long before my divorce, so it didn’t take no time for the pressure to build up in my aching balls and shoot the biggest load into Tommy’s tight asshole. He kept pumping himself on my cock even as I was groaning and coming inside of him. He clenched his sphincter tighter around my cock like he was trying to coax more come out of my testicles if that was even possible!



I guess he realized I was finally spent as he slowly got off me and laid down next to me. Before I even knew it, he reached down and took my messy cock back in his mouth and licked and sucked the come and the taint off my subsiding erection. And, much to my surprise, he grabbed my jaw and forced it open and spit the gunk into my mouth. This time I felt like I was about to gag, but I held it in and even swallowed all of what Tommy had spit into my mouth. Tommy apparently had a sadistic streak in him as he just closed my mouth shut as he let out a rather sinister-sounding laugh. Before I even had a chance to respond, Tommy tapped me on the shoulder and said almost like a warning, “Now it’s my turn.” He tapped me on the shoulder again and ordered me, “Get on your stomach, bitch!”



Without hesitating, I did as he commanded and laid down on my stomach in anticipation of whatever it was he had planned for me, although I had a pretty damn good idea! Without wasting any time, Tommy spread my ass cheeks apart and stuck his mouth and tongue into my asshole like i did with his. He both licked and tongue-fucked my asshole like he had done this many times before, of which I had absolutely no doubt that he had. My anus soon became lubed up with his saliva. He then climbed on top of me and mounted me as he shoved his cock deep inside of me until I felt his balls touching my ass. He placed his hands on the mattress on either side of me again and fucked my ass as hard and as fast as he could. He was so forceful with me he practically raped my asshole, though I certainly didn’t mind!



I guess with him being younger than me he had more stamina than me as he was able to hold out longer than I did as he fucked my ass faster and faster, the sound of his balls slapping over and over again against my ass. With my face buried in his dingy pillow, I felt his hot breath striking against the side of my face as he leaned his face close to my ear and whispered, “I’m gonna come in your ass. Are you ready for it?”



“Yeah,” I gave out a muffled groan, “I’m ready!”



“Okay, bitch,” he groaned, “here it comes!”



With that, he practically screamed in my ear as I felt his hot come filling my ass and spilling out over my ass and down the inside of my thighs. He pumped and pumped his cock in and out of me some more until I guess he coaxed the last drop of come out of his drooping balls. He finally climbed down off of me and licked his own come and taint from off of my backside and, when he was done, he grabbed my face again and forced my mouth back open and spit his shit back into my mouth. Again, I thought I was going to throw up, but I managed to keep it all in and swallow it all down. Tommy patted me on the back like I was some kind of dog and said in an almost mocking tone, “Good bitch!”



He laid down beside me on the dirty mattress after fishing out another cigarette from his purse and, after lighting it up, asked me with surprising tenderness, “You wanna spend the night?”



I did, and i did. I kept seeing Tommy after that first intense night with him. Not wanting to see him live in that condition any longer, I invited him to come live with me, which he eagerly accepted. He got a job as a griller at a local fast food restaurant, and he became my live-in lover. I’m not sure what the future holds for me and Tommy, but I will say I wouldn’t change a damn thing.



Except, of course, for my nasty divorce!

My new partner is not really a girl’s idea of a “ladies man.” Nevertheless I have known Joe for a long time and when he asked me out I jumped at the chance. I had no illusions about Joe but one asset he does have is a decent bank account! His parents had died and left him with a nice house. He does have a regular job but I also knew that he was comfortably off with an inheritance. Joe is just 28 and I am 33. As far as I know Joe had never had a regular girlfriend. He was far too shy and reserved.



My former husband was a womaniser with equipment to match and he was forever seducing a female. Any female, young or old, it didn’t matter to him. I finally told him what I thought of him and he kicked me out.



Call me cynical but don’t get me wrong. I quite like Joe. He is attentive and kind and I am kind to him in return.



All I want from Joe is security and I am quite sure that Joe can’t believe his luck to have an attractive live-in partner.



The first time he asked me to his house and made a pass at me I played it cool and pushed him gently away. Joe immediately apologised and blushed.



I told him not to be silly and I really liked him. “You may kiss me if you like,” I told him condescendingly.



Poor Joe. He just didn’t understand women. Perhaps I was his first “conquest!”



Did I actually have to seduce the poor boy?



Finally he plucked up courage and his hands began to explore my body. First he touched my breasts and then his hand fell to my thigh and began to slide under my dress. Excitedly his hand was beyond my stocking tops.



“Oh, please don’t Joe. I know I won’t be able to resist you if you don’t take your hand away!”



Joe quickly snatched his hand from under my skirt and blushed bright red and apologised again.



It was time to take the initiative. I held his face in my hands and kissed him full on the lips. “Darling, when I say please don’t, it doesn’t always mean just that!” With that I stood up and lifted my dress before brazenly pressing his face between my legs and allowing my dress to fall over his head.



At last Joe got the message. I allowed him to fumble behind me with the zip of my dress and he gasped as it fell to the floor. He was alone with this sexy woman in her underwear!



I undid his belt and pulled his trousers and pants down. His tiny dick was throbbing with excitement.



“Oh Joe, you are sooo big. Please be gentle with me!”



Fortunately I am a good actress and he was convinced he was the world’s greatest lover. In reality a few excited thrusts and poor Joe collapsed on top of me.



I moved in with my shy boyfriend and inevitably I was boss. He is such a wimp and after all I am older than him. I am patient with him and we get on quite well together. Our sex life continues to be a disaster, although I make sure that Joe proudly believes he is OK in that department.



Playfully I began to adopt the role of the dominant mistress. I could see that this excited him and one day, when we had a slight disagreement I boldly told him that he was acting like a naughty schoolgirl and I should smack his bottom!.



I wondered how Joe would react to that remark. After all wasn’t he supposed to be the man about the house? But Joe was keen to enter into the little charade. We both laughed as we jumped on to the bed and I pinned his arms above his head and warned him what happened to naughty schoolgirls. “They get their knickers pulled down and their bottoms smacked!”



Joe was up for it. “But I haven’t got any knickers on Miss!”



We both giggled as I produced a matching slip and panties set.



“Oh no,” said Joe, “Oh no.”



But I was having none of it. “You must learn to obey your mistress,” and with that I proceeded to strip him. After pleading with me to stop Joe soon stopped struggling and allowed his tormenter to dress him in a sexy slip and matching knickers.



I noticed that he was no longer laughing. Neither was he protesting and it dawned on me that he was actually thrilled with the idea of being girly.



I slid my hand underneath those satin silk undies and began to masturbate his tiny dick. Soon I made him cum in his knickers.



I kissed him. “Did you like that Josephine darling?” I said.



Joe blushed scarlet with embarrassment. “Oh what I have I let you do to me?” he said. “And please don’t call me Josephine!”



“It was only a bit of fun Joe darling. Admit it. You secretly liked being a girl and you certainly excited me.”



Joe looked at me. If I had made his lovely new girlfriend excited perhaps it was OK. After all he had to admit to himself that he found being a girl just so wonderful.



Our sex games continued and always in much the same way. Joe would protest as I found a reason to scold him and told him what a naughty girl he was. Then we struggled but it was always just a token struggle and somehow Joe found himself once more wearing my sexy undies. I could see that once he was in girly underwear for him the game was over and he was totally turned on and eager and ready for me to satisfy him.



He is completely under my control and I can see that he adores the feeling of total submission. We often sit on the bed or the settee and I put a motherly arm around him and my other hand will expertly bring him to his excited climax. For the first few times after he had cum in his knickers he would be embarrassed.



“Darling you are blushing like the little schoolgirl you are,” I told him. Then we laughed together and Joe believes that it is just as exciting for me.



I never feel sorry for Joe and his femininity and I actively encourage him. We never ever have straight sex now but I am sure much prefers me to satisfy him in the expert way I do. Joe has found his true role. To be sexually dominated by his adorable partner. “You can call me Josephine when we go to bed if you like,” he told me.



As for me, I have my lovely vibrator. Better than any man!

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