Prior to the internet hookup, the only way to connect spontaneously with other horny people was through calling local phone connections. You know, the ad you see in your local entertainment rag with a rippling hot stud running his own fingers through his hair that offers free postings for people who want to connect within the city. It was such an ad that inspired me, Jonny, or Ashley, as I prefer, to post an ad and take a call from a man named Trevor. Trevor responded to my ad that said, almost verbatim, and in a lame girl voice, "Hey Y'all, this is Ashley, I am 5ft 7inches tall, blonde hair, blue eyes, 146 pounds, smooth, in shape, trim, and I love dressing up as a girl and pleasing men. My body is smooth, I am passable, and I am the best fuck you'll ever have. If any of y'all out there are interested, just leave me a message and I'll get back to you." Having submitted the message that morning I went to get some essentials from the drugstore. I purchase all my makeup, pantyhose, etc. from the neighborhood pharmacy. They all smile when I walk in. Women are always sweet to me, and most guys are, too. I've determined that the ones that aren't as sweet to me are the ones that really want to fuck me. I think women are nice because they see what great lengths I go to trying to emulate them. I have a real sweet girl at the makeup counter who would act as my consultant on purchases. The first time I came in I probably looked like a circus clown. She periodically over time taught me how to use more subtlety and to actually look prettier. The first instinct of a man trying to make the transformation to woman is the tendency to put on too much makeup. Julia, the clerk, taught me how to do my eyes, and how to put on foundation and blush that didn't make my cheeks look like swollen red balloons.
After my visit with Julia I went home with my purchases to take a bath. I filled the tub and while waiting decided to check to see if anyone had left me any messages from earlier. I had 3 messages! Upon listening I found out that two of those were the same man jerking off into the phone and screaming, “Take that, bitch, oh yeah! fuck yeah!”, and one from Trevor. His message was nice and simple.
“Hi, my name is Trevor, and I just wanted to say hello, and I hope you’re having a good day. I love sissy boys, and I would like to meet you to find out if indeed you’ll be the best fuck I’ve ever had. I’m 6feet tall, 190 pounds, black hair, and green eyes, and I have a 7 inch cock that is almost as wide as it is long. I have plenty of places we can meet, so call me as soon as you can.
Hmm, I thought, intriguing. I went on with my bath and imagined what might transpire with Trevor.
Sidebar- At the risk of being redundant, if you’ve read any of my other stories, then you know that I think that a man who really gets off on dressing up like a girl and getting fucked like a girl probably has more sexual energy than anyone else on the planet. In other words, no matter how many times I or anyone else makes me cum I am ready for more almost immediately. It is an insatiable appetite for feeling numb in my libido from pleasure and pain that cause me to go to great lengths to keep myself sexually satisfied. I like the feeling of things inside my body. I like to feel like my body has been violated, but in a good way. This is a long drawn out way of telling you, dear reader, that I jerked off in the bath imagining what Trevor may have been like!
I called Trevor after putting my hair up in a towel to dry. I was blessed with hair. Long, natural blonde hair that flows about midway down my back. It’s gorgeous, but a bitch to dry and make pretty. Guys, never give your girlfriend, wife, or tranny a hard time about their hair. They aren’t bullshitting when they take a long time getting it ready. While my hair was up I thought I’d paint my toenails and lob a call to Trevor to see just what this message was about. While painting I dialed, and he answered on the first ring.
“Hello,” said Trevor in a chipper tone. He sounded sweet!
“Hi, this is Ashley, I was returning your call from a message you left in my mailbox, how are you, sweetie?” I asked.
“Fine, thanks,” said Trevor, “and how are you, my lady?”
“I’m fine, thanks,” I said, trying to sound hot. I have a pretty lame girl’s voice, but it worked enough to get the illusion across. “So what’s this I hear about you having several places for us to meet?” I said.
“Well, sweetie, I am a real estate agent. I have homes that I show all over town that I have keys to. I know which ones are occupied, and obviously which ones are not. Some are furnished, some are not,” he said. “What part of town do you live in, sweetie?”
I told him I lived on the west side, and after asking to be more specific, I told him I live on Central Blvd.
“I happen to have 760 Central on my list of homes,” said Trevor. Correct me if I’m wrong, sweetie, but aren’t you in the market for a 4-bedroom two-story house?”
“I sure am,” I said, “and I’d like to see it today.”
“That’ll be no problem, ma’am,” said Trevor, “However I’m going to have to insist that we first meet over a glass of wine at Bruchelle’s. Do you know where that is, sweetie?”
Bruchelle’s was an Italian restaurant about 12 blocks from my house.
“I sure do, sweetie,” I replied.
“You said you were passable, right Ashley?” said Trevor.
“Of course I am, sweetie,” I said, trying to chuckle like a little slut girl.
“Well, look real nice and meet me at Bruchelle’s in an hour,” he said, “does that sound ok?”
I hadn’t even begun to do my hair, so I asked if he could give me an hour and a half, to which he agreed. So I began to get ready. It takes a girl about an hour to get ready and that is rushing her. It takes me a little longer, because I have to conceal my cock and that is rushing me. I like the ritual of dressing up anyway. Before I had the nerve to act on impulses for getting fucked, all I had was dressing up. I’d I like my freshly shaved legs to completely dry and cool off from a hot bath, so they feel good when I slide on pantyhose. I always start with panties, and I always wear satin panties. I have an apparatus that is essentially a piece of velvet felt tied to a g-string that I run between my legs and through my crotch, tied in back around my ass. It tucks everything in front between my legs and leaves a smooth patch where my dick is usually protruding. I slid on my panties, got a matching pink satin bra (I love Victoria’s Secret mail order!) and slid on my pantyhose. These pantyhose were nude colored and were perfect when you like to show leg or wear a short dress. I had a cute sundress I bought in Miami when I was visiting a girlfriend of mine that I chose to wear. A sundress is not the best thing to wear with a regular bra, as your straps hang out of the shoulders, and the actual top of the bra is exposed on the sides of your frame, but when you are in it for the thrill like me, there is nothing in the world you like more than to have your bra showing! (I know I’m such a detail queen. Don’t you love it??!!) I sat down at my makeup table and applied my face. Elvis played on my little bedside radio. I like listening to Elvis. He makes me so horny. If I do have female hormones anywhere in my body, and I know I do from the pills I’ve taken, Elvis makes them go crazy. Needless to say, I listen to Elvis a lot! His voice makes the middle of my crotch tingle. There’s a compilation of songs that I listen to when I’m dolling up, consisting of tunes including, but not limited to, “Devil in Disguise,” “His Latest Flame” and “Teddy Bear.” The last step in my preparation, and certainly the most learned mannerism I have conquered was heels. I slipped on my red heels and slinked out of the house to Bruchelle’s.
I actually arrived before Trevor so I got a booth in the corner and ordered a chardonnay. About 5 minutes elapsed before he arrived. He was a nice looking man, well kept, with a suit on. Men in suits drive me crazy. He arrived and let himself in the booth, giving me a kiss on the cheek as he sat down.
“You look nice,” I said, “very nice.
He smiled and gave the compliment back, saying, “You, my dear, are better looking than you led on.”
We sat in silence, smiling at one another and sipping white wine before he piped in,
“Now Ashley, the house on Central is absolutely gorgeous. You won’t believe the master bedroom. It has a king size bed in it that backs up to a Jacuzzi tub and a generous walk in closet. It is the signature room of the house. It is absolutely beautiful. When we finish our wine I’m going to ask that you let me get a head start over there, ok?” He was rubbing his foot up and down my leg in the booth as we gazed at each other. That drives me fucking crazy. I wish all people, men and women, could feel the pleasure of someone vying for your sexual favors in a public setting. To have a man slip his shoe off and run his toes up and down my smooth legs in pantyhose had me foaming at the mouth. I kept spreading my legs wide as he would get to the top of my thigh, but he couldn’t get any further without his knee banging the underside of the table, to which he did a couple of times. He smoked cigarettes. He lit up and asked me if I wanted one. I didn’t smoke, but went ahead and got one from him hoping it would relax me. He finished his smoke and pecked me again on the cheek, saying he was off to tidy the house before I arrived. I ordered another chardonnay and fixed my lipstick, went to the ladies room and proceeded to get back in my car to go to the house. Cue Elvis Presley!
As I rode back I was wondering why he wanted to meet me in public first. I can only assume that if I hadn’t passed his inspection at the restaurant then he was probably planning on making a speedy getaway. I pulled in to see his Cadillac parked in the circle drive, and he was in the window of the master bedroom. He knocked on it as I got out of my car and walked up to the house. He motioned that the door was open so I let myself in. I walked upstairs to the master bedroom and he greeted me, wrapping his arms around me and kissing me deeply. I kicked one leg up in the air as he wrapped his arms around my tight little frame and squeezed the breath out of me. I rubbed his cock through his pants and felt it immediately respond to my touch. We made out for a few minutes as his hands started to wander below my dress, hiking up my little skirt and rubbing my ass cheeks. I love for a man to have both hands implanted on each of my ass cheeks, squeezing and prying at them, gently slapping them. I began to breathe heavy as he was a pro at making out. He was running his hands all over my body and I to his body as well, though my central focus was his cock. With one hand he pushed the top of my head down to his crotch area, and I promptly unzipped his pants to pull out his cock. He had amassed such a hard on that I had a hard time getting it to go through the fly hole of his boxers. He wasn’t kidding when he said his dick was wide. It was obnoxiously stubby, and it wasn’t all that short, it just seemed like it because of its width. I love kneeling down to a man’s crotch and sucking his dick at that level. It is an unbelievable feeling to be able to shoot your eyes up at a guy while on your knees sucking his cock and see that he is in such pleasure that has been derived from your mouth and tongue. It is empowering to me. Some might think it is the ultimate in no self respect. I think it is the opposite. I have this man’s cock in my mouth, he is writhing in ecstasy over a sensation I am giving him. It makes me hot. My cock hardly ever gets hard. In fact, when I am most turned on, my cock is essentially nonexistent. It is so secondary to my back pussy that it often takes time off when I’m with a guy. I don’t blame it. For my purposes, it is useless. He gripped my head, twirling a handful of my hair up into a ball in his hand while he guided my face down on his cock. It began to almost make my jaws hurt his dick was so wide, but after a while I got used to it. I could feel his shaft on both sides of my teeth. I had to open extra wide to be sensitive to his cock, as this is important in getting the maximum amount of hard cock for your pussy. One false move with your teeth and the guy can lose it completely. He kept telling me how beautiful I was, and I kept cooing and slurping at his dick, looking up at him with my best seductive eyes while I sucked his manhood. I closed my eyes and that’s when I felt a tight pull on the back of my head. He had a handful of my hair wrapped around his fist. My hair that I’d spent so much time making pretty for him. He began to forcefully push my head down on his cock, forcing me to go as deep as I could, rubbing my lips and nose up into his pubes. He moaned and grunted, rolling his eyes back in his head as he simultaneously rammed my head into his crotch, and saying stuff like, “Suck that fucking cock, you little whore,” or “Take it all, you bitch suck that head. Don’t you want my cum, bitch?” I did want his cum, but I was enjoying being romanced instead of just being a fuck and suck toy. I felt myself fighting for air, as he had harnessed my face with his dick and was riding my lips like a bucking bronco. His inordinate thrusts disabled my ability to get a good rhythm going, and I was also battling the fight for oxygen as he was keeping my mouth full with his dick as he forced my lips down to his balls. I resisted the gag reflex, and the more I pulled my head away from his dick, the more he forced it on me. Your mouth, like your ass, reaches a point where it gives in, and everything that once seemed too large becomes just right, or in some cases, too small. I got used to his offbeat rhythm and began to conform to it, licking and swirling my tongue around his cock. I felt his hand relax a little on my hair and I thought I had him beat. I began to lap really hard at his cock, taking the full piece over and over again fully into my mouth. His hand almost released completely so I got a little sweeter with my mouth, and resumed what I normally do, which is lick and kiss the shaft from all different angles, letting my long flowing hair graze his balls and legs. His pants were around his ankles at this point. I took his cock with one hand, and began gazing up at him again, giving him eyes that told him that I was ready for his load whenever he was. It was at about this time that his hand gripped my mane again, yanking my head back off his dick as hard as he could. He wrapped the hair around his fist and pulled me to the ground, slapping my ass and asserting his body onto mine as he whispered,
“I’ve got to show this house in 45 minutes, and in that time I’ve got to fuck your ass, do you understand?”
I really wasn’t enjoying this like I’d hoped, and was beginning to feel a little threatened. He gripped my hair even tighter and repeated, “Do you understand?” to which all I could do was nod. He then pulled me up off my knees by my hair. My legs were relaxed from being on my knees so I had a hard time catching my balance, and an even harder time wearing my heels. I fell over and he didn’t miss a beat, pulling me by my hair across the floor to the bed. He literally pulled me up by my hair onto the bed, then began caressing my legs with his free hand, keeping one completely entangled in my locks. He forced my face down into the bed. He ran his face down to my ass and bit my right cheek as hard as he could, to which I let out a scream. It actually felt good, though, once the initial sting wore off. Remind anyone of anything?!
“Shut the fuck up, Ashley,” he said, “shut the fuck up or you won’t get fucked like you deserve, you stupid bitch.”
I was scrambling to get away. Every girl, or every guy that dresses up like a girl has this fear of resentment. I usually keep my defense mechanisms up before I let my fears subside and become the girl I always wished I was. You always fear that someone will lure you to bed then beat the shit out of you because you are trying to be who you want to be. I had to tell Trevor this before it got to that. He had my hair completely twisted in a knot in his hand and was holding my face down into the mattress.
“Sweetie,” I mumbled, but he just pushed down harder and kind of chuckled. I tried again, “Trevor, please!” I said, to which he replied, “Shut your mouth, you hot little cunt. I know your type. I know how much you love getting pushed around, trampled upon, and grudge fucked. I’m going to give you everything you want right now, like it or not!” He said, pulling his shirt off with his free hand while he kept me captive on the bed. He began to rip at my dress, which was halfway off of my body from the vicious manner in which he flung me on the bed. As he reached at my chest, and grabbed the strap of my bra to yank it off of me, I felt a second wind, one that sensed everything might be okay if I just went with the flow. As my bra popped off my body I felt the strap slap my skin and it stung. It felt like someone hitting me with a ruler. It kind of turned me on. I began to call his bluff.
“Oh yeah, baby, get me good, you big fucking hunk,” I said. It kind of slowed him down,
“You like that, you little cunt?” He said, and I realized that I kind of did.
“I like that, baby, now let’s see if you can back it up. How hard can you fuck me, you fucking stud,” I said, voice muffling through the sheets as my face was still buried in the bed.
He pulled my face up close to his and whispered to me, “No one can know we were here, you understand?” he said. “We can’t leave a trace of anything to let anyone know that I fucked your pussy on this bed, or I’ll lose this listing, and this house means a lot to me, got it bitch?” He began caressing where my twat should have been with his other hand, rubbing the satin crotch and slapping it like I had no cock at all. I had it hidden pretty well, but it is still very sensitive. He thought he was turning me on by the kind of moans I was making, but I was in sheer pain. His misinterpretation led to even more violent slaps, and I all I could see from what little view I was afforded from having my face slammed into the bed was his unwrapped cock making it’s way towards my back pussy. As scared and as excited as I was, I didn’t like the look of an unprotected cock going towards my hole I was so proud of, and I tried to tell him.
“Please,” I said, panting and moaning, “please don’t fuck me without a rubber, Trevor.”
I was proud of the fact that no one, not even my virgin fuck had been in me unprotected. I had played hard, but felt confident in my cleanliness as I’d always used rubbers. He wrenched his hand down harder on my hair and put his mouth in my ear and whispered at an accelerated and primal tone,
“You don’t have a goddamn thing to worry about, you fucking hole. I have too much on the line to risk my life over some skank fuck like you.” He wrapped the hair even harder around his hand.
“Now, tell me honestly, are you clean? I am clean you bitch, are you clean?”
At that moment the pain from head being pulled so tight by my hair began to settle in, and I felt a calming come over me. That pain felt good all of the sudden. It had reached a threshold that made it not only painless, but somewhat comfortable, as the heightened sensitivity had been numbed on my head. That same numbing was occurring on my crotch, as Trevor had steadily been slapping and caressing between my legs with his other hand, slapping his cock up against the tight satin crotch. I was beginning to settle in. I thought for a moment, as this man had me entangled in his arms on this bed, threatening to fuck my hole with his bare cock, and I knew I was clean.
“I’m clean,” I said, “Fuck me, you fucking hunk,” and closed my eyes and held my breath. With that Trevor pulled my panties off of me, then ripped my crotch tucking g-string from in between my legs and proceeded to line up behind me, spoon style. He kept a grip on my hair, and now, different from before, I actually wanted him to pull it harder. He began spitting in his hand and rubbing it in my ass. I felt like my ass would hardly need lubrication, as I’d worked up a bit of sweat trying to resist his advances. He kept spitting in his hand and rubbing it my ass. As soon as I would think he had lost a bit of his edge, he would remind with a coarse slap to my ass, one that would make me yelp into the mattress unheard. His primal whisper resumed,
“You’re going to need a lot of lube for that tight pussy, Ashley” he panted. How sweet, he said my name!
His lips bit into my neck and I winced as he lunged his cock into my hole. He was right. The enormous width of his cock was finding it difficult to wedge into my tight little pussy. I tried to free an arm to help spread my cheeks to get it in me but he forced me back down. He spat again and rubbed it directly on his cock, then forced it into me. I was overwhelmed with pain and pleasure simultaneously, and tried to settle in for what was sure to be a bumpy ride.
He pushed it in and out in short jab like manners until he had successfully intruded his full piece. It was beginning to feel good.
He had my hair still in his grip and began pulling it with each thrust he was making into my body. I finally was able to lift my leg up a little bit, giving that extra ¼ inch in my back pussy that helps a lot when being fucked so hard. He began furiously stabbing my ass, and I felt helpless. He was pounding hard. It was sending ripples through my body. He pumped and pumped, whispering insane little quips into my ear like, “Fuck that hole ‘til it swells,” and, “take all that fucking meat, you bitch!” That unwrapped cock felt so good, so natural, it was the best feeling cock that had ever been in me. It was driving my pussy crazy. I told him I was about to cum, as his cock was nailing my prostate and it was at its peak.
“What did I tell you, bitch! No evidence!” He yelled.
With that he let go of my hair and ordered me to put on my panties. I scrambled for them on the floor, falling over on the ground from losing my equilibrium that had been damaged by his hair pulling and thick cock fucking. I scurried on the floor to get them and no sooner than they were in my hands he grabbed my hair again and forced me down.
“Put them on, bitch,” he said, “put them on now.” I hurriedly put them on as best I could and he let go of my hair again and threw me on my back. He pulled the panties to where he could reach my ass but my cock was tightly covered. He flung my legs on his shoulders and applied a pressure so that I was helplessly trapped, as my shoulder blades were in line with my head and stuck his dick directly back in me. He was right on my prostate. About 20 good strokes and I was there again, squirming and wrapping my cheeks on his cock, looking at him like a scared animal that had been pinned in the wild by its predator. I began to cum, and my panties had my cock wrapped tight, soaking up as much as they could, and I was cumming in heated spurts. He noticed my orgasm and began pumping furiously, grunting and sniffing, like a goddamn animal. My ass was completely numb with pleasure, and I was in a state of erotic bliss. He told me he was about to cum, and leaned right into my face, saying, “When I cum, you better be ready to catch it with your panties, bitch. One drip and you’re fucked.”
To which I replied, panting, barely able to breathe, “But I’m fucked already, baby”
He pushed down on me with all his might and began to fill my hole. I had never felt this before. Gushes of warm, squishy fluid formed a sort of mucous bonding to my ass and his cock. He kept ramming it harder, forcing all the fluid as deep into my body as it could get. I began to cum more. He had exhausted all his energy yet still remained tightly on top of me, his cock fully inserted in my body. When he finally began to pull out he took my hand and put it between my legs on my panties. His cock came out and he kept it atop my asshole while I put my panties in place. He then put his cock on the outside of the panties, wiping off whatever cum was left on him into my underwear.
“Keep your legs up in the air,” he said, pulled my pantyhose up from my ankles. He slid them down my legs that I had kept up in the air as he told me and put them snugly around my waist.
“Now, get up” he said, to which I did. I could barely walk. I was still shivering from being fucked and cumming as hard as I did. I turned to him and he smiled and winked, then said, “Now get the fuck out of here.” I looked for my purse and an earring that had fallen out somewhere in the room. He ran up behind me, slapped my ass as hard as he could and told me to get out. I began walking towards the door, confused and sloshing what seemed to be a gallon of cum in my panties. As I walked I felt cum seeping out of the crotch and down my legs, running down my pantyhose. It had cooled off some now, and was thicker than when it was first shot. It was cooling off my inner thighs as I got my breath and exited the house. My body and clothes were a wreck. It had been a miserable yet incredible experience all at once. He truly fucked me like a piece of meat. Screw that girly shit, I was a piece of meat. Upon leaving I looked back up to the window and there he was, smiling, looking as innocent as when I arrived, waving rather harmlessly down to me, like I was a pretty girl again. I made a confused wave back to him and got in my car, fixing my makeup, not knowing whether to cry or laugh. The cum was oozing out all over my car seat, as the panties and hose weren’t enough to hold it. I looked up to the other end of the circle drive as a car was pulling in. I began to back up as they looked at me, but I just acted like I was lost and turning around. Out walked Trevor, completely cleaned up and looking as dapper as when I met him in the restaurant.
“You must be the Simmons!” He said, walking out and shaking their hands. “Let me tell you about this house. It has a wonderful master bedroom, with a....etc”
I pulled out, went home, and after careful deliberation, called Trevor’s office to book an appointment to see more houses. The End