I'm always weary of chat room hookups. For one, I don't "chat" much, and two, I'm still rather closeted when it comes to my fascination with women's clothing and playing the woman's role in sex. I don't share that often. I try to mask it as best I can, but the urges are tremendous at times. I go to chat probably twice a year. So when I do, I try to make it count.
I found myself surfing one night back in December. It was cold out, not much to do, so I figured I would give into my urges to dress up in girls clothes and talk on the internet. It's always a rush to "shop" your fem booty around to local guys looking to get laid. It's also so pleasant to shave your legs and underarms in the winter, slip into hose and panties and a bra, doll your face up, and sit around chatting with would-be suitors. I'm relegated to gay sites, and I wish there was a network strong enough to support tranny chatters and hookups exclusively, but I don't know of one. (If you do, please let me know!) A lot of gay guys however are turned off by girly boys, so surfing is a little more scarce. The waves can be lame. Sometimes I don't reveal that I'm into being treated like a girl until later in the conversation, so that maybe I can seduce them with my typing charm before they get turned off by a boy in panties and make-up.
I looked tirelessly through the guys, one by one. I ignore advances from guys that are really into themselves, because they waste time. I look for guys who like to impress whomever they are talking to. You know, guys who act like they are interested in you, and most importantly, are interested in digging around in your back side. When you like to be the girl, you enjoy pursuit, but it’s got to be in a manner that is not psychotic. Remember, it is often the tranny who feels psychotic, with my painted face and shaved body, decked out in satin and lace, pantyhose and a dress, the last thing I need is for someone to scare me. I’m a nervous little bitch as it is! Part of the excitement is that feeling of potential domination. The feeling that you could excite a man to full erection, have him fuck you silly, and let him release all over you, all because of you and your sweet back pussy.
I had been on for several hours surfing when a guy popped up to chat. His name was “Harry & Company”. Harry described himself as 6 feet 3 inches, 190 pounds, 35 years old, brown eyes and hair, and you guessed it, very hairy.
“How are you, Ashley?” said Harry.
“Fine, thanks” I said, “just a little bored.”
“Why so bored?” asked Harry.
I had been drinking while typing and fantasizing so I was a little loose at the lip with him,
“Because I’ve been on here for what seems like all night and no one wants to fuck!” I typed. I didn’t even know if I wanted to fuck at the time, but wanted to feel him out.
“I might want to fuck, sweetie,” said Harry. “What are your stats?” asked Harry.
I thought it would be funny to give girl measurements so I spouted back, “36-26-36, but the first 36 is fake!”
“I see,” said Harry, “little girl is feeling all alone, huh?”
“You bet,” I replied, “ I need a man to settle me down, because everything between my legs is going crazy right now.”
That wasn’t just a line. When I’m in full makeup and girls clothes, I am a hormonal freak show. I am so fucking aroused. I feel so much more vulnerable to sex, but in a good way. I love to feel like a slut. I love to spread my legs and rub on my crotch and asshole.
“What are you wearing?” said Harry.

“Black satin panties and bra, black hose, a black dress and makeup” I said.
Harry didn’t reply right away. I thought I had turned him off.
“Harry?” I asked. “Harry?”
No reply for a few minutes, then finally an answer.
“You just got me hard, you little slut!” typed Harry. I felt my pulse increase.
“You just got my dick rock hard, you little bitch. Why’d you go and do that?” typed Harry. My heart was racing. I could barely type the response,
“Because I want to fuck and suck your cock until it rains cum all over my rosy red cheeks” I typed, all the while rubbing my satin crotch with my free hand.
“Do you like girls, too?” Harry asked.
“Of course I do, I love them. I love being around them. I love their bodies, their smell, their hair. I wish I had a body like a girl. I wish my life was like a girls. I want to be a girl,” I said.
“Call me right now,” Harry said, and gave me his phone number online. I was trembling. A lot of times I talk a mean game when it comes to being with men, but I chicken out sometimes as well. If I don’t feel right about the guy, then I start to feel nervous. I didn’t call right away and I got another message from Harry on the chat board.
“Call me right fucking now, you sweet little bitch,” said Harry.
I took Harry’s number and called right away. I was nervous about what could transpire in the near future, I also knew that when a man snaps at you like Harry did on the message board, calling me a sweet bitch, then it makes you kind of subservient and quick to dial.
I made another martini and called Harry. (By the way, when you get off so hard on dressing up and acting like a girl, then even seeing your lipstick on a martini glass gets you horny)
“Hello,” said Harry, “Is this my sweet bitch?”
“Hi, how are you?” I said, in my best girl voice, which is essentially just a really gay man sound.
“It is my sweet bitch,” said Harry, panting over the phone so I could hear him.
“Yes, it’s your bitch,” I said, “are you my stud?”
“Oh, I’m your stud, alright, “said Harry, “I’m the stud that’ll make you feel like the sweet little thing you wished you were,” he said.
I had a lump in my throat. I wanted to replace that lump with Harry’s cock.
“My wife and I would like to see you, sweet bitch,” Harry said, “we want to play with your body. I think you should come over right now,” said Harry, breathing heavy all the while. I think you should come over and get dicked, you little slut,” said Harry. I could feel my heart pumping fiercely, right through my bra, making my fake tits pump with every breath.
“Where do you live?” I gasped, by now totally encapsulated by this chance encounter that I might be so lucky to be a part of.
Harry lived about 5 miles from my house. We made plans to come over and Harry started quizzing me about how I liked it.
“How do you want me to be waiting for you, bitch?” asked Harry, “Do you want me clothed or nude? Do you want me to leave the door open so you can let yourself into our bedroom, or do you want me to meet you at the door, like a true little bitch girl?” said Harry. Of course, I chose the true little bitch girl option.

“Meet me at the door,” I said. “I want to see you before you have me.”
“You better look good, you better look like a sweet little bitch girl” said Harry, “I expect makeup, pretty hair, and a slutty dress, you understand?”
Oh, I understood!
“How do you like to be fucked, Sweet Bitch, and what’s your name, apart from Sweet Bitch?” said Harry.
“Call me Ashley,” I said, faintly, “Call me your Sweet Bitch Ashley.”
“Ok, Sweet Bitch Ashley. Now answer my question, how do you like to be fucked?”
“I have always preferred missionary. I like to have a man part my legs and hold them up in the air while he wails into me, letting me see his face and body intensify with every heave into my hips,” I whispered.
“Get to my house right now,” said Harry. “My wife and I are waiting for you, Sweet Bitch Ashley. My wife is going to sit on your face and let you eat her pussy while I fuck your little tight pussy, ok?” said Harry.
Was I dreaming?!
I hurriedly checked myself in the mirror, fixed my hair up and threw some lipstick and mascara in a purse, grabbed my lube and a to-go cup for my martini and set out across town.
I tried to get myself more in the mood riding over there, putting some Elvis love song compilation on to get me hot. Elvis was so gorgeous. He could melt a girl’s heart with that sweet voice as well. He was melting me on my drive to Harry’s. The phrase “Love Me Tender” means a lot to this girl. I like to be fucked hard as well, but I love to be fucked softly and sweetly. I like a man to get his full compliment inside me and begin to stub thrust his cock into my hole. I love the feeling of full insertion and repeated penetration, too. But I love for a guy to get his entire cock inside my hole and have his cock pulsate while he takes very small jabs at my pussy. I love to make out while he’s fully inside me, wiggling my ass cheeks to further get him entirely in me, sticking his tongue down my throat as deep as he can get it, and letting my hands race up and down his back, from his shoulders, to his ass, to his waist, and to his legs. I love the feeling of being at full capacity from every orifice. It makes me hot. It makes me cum. My favorite thing in the world is to cum without provocation. I love having my ass penetrated so deep that I cum from the friction on my pelvic bone. My cock doesn’t even really get hard. It is so in submission that it just spurts cum, and spurts it in massive amounts while flaccid. It is as close to a girl orgasm as I can get.
I pulled in to Harry’s driveway and checked my makeup in the rear view mirror, fixed my hair up again, and then proceeded to Harry’s front door and rang the doorbell. He opened the door cloaked in a velvet robe, his robe opened up to see his rippling hairy chest. He had a full beard and moustache. His eyes were fixated on me. He met me at the door, took my hand, drew me into him, and gave me a long, deep kiss. I could feel myself quake as he put his arms around my waist, sliding his hands down the back of my dress, lifting up the skirt to rub his hands on my ass cheeks while he French kissed me. His wife, Tawni, came up to me as well, rubbing her hands all over my body while Harry made out with me. She was a cute lady. Shoulder length blonde hair, green eyes, and stood about 5 feet 3 inches. She kept rubbing my crotch while Harry had his way with my face. Her hands dominated my front side and Harry had each hand gripping an ass cheek, spreading my cheeks apart, running his fingers into my crack, carefully penetrating, then pulling back. I was shivering in pleasure. Harry stopped kissing and took me by the hand, leading back to the bedroom. Tawni walked behind us, whispering things like, “nice ass, you little bitch,” and “girlfriend’s gonna get fucked real good.” For everything she would say I would swoosh my ass out as good as I could, letting it fly in the air, hiked up in anticipation of Harry’s cock. Harry repositioned his arm to wrap around me like I was his wife. That is such a comforting feeling. His wife had gotten close behind us and was slapping my ass with her open hand as I was walking.

Harry stopped upon entering the room and kissed me again. His wife vanished and he quickly pulled his pants down to reveal his cock. It was nice, about 7 inches long, uncut, and rock hard. I immediately dropped to my knees and rifled his rod into my throat. He grabbed the back of my head and began to force my lips around his cock. I eagerly lapped at his dick with my tongue, panting and breathing heavily as I inhaled his whole cock. It would throb in my mouth, almost making my jaws lock with the sudden burst of excitement. I would never let it choke me. I loved every minute of eating his cock. I love having a man’s hands on the back of my head, forcing me down on his dick while he thrusts into my mouth. I love to feel his thumbs behind my ear lobes, grabbing my head like it were binoculars on top of the Empire State Building, and spinning my mouth and head every which way around his cock. I could feel pre-cum oozing out of his hole, so I lapped it up and licked all around his foreskin, swapping my spit for his cum. He pulled me up to him, ramming his tongue down my throat, chasing whatever remained of his pre-cum. I kissed him back aggressively and he pulled the back of my hair real hard with his hand yet pushing my head into his while kissing back. He pinned me against the wall and began to kiss my body. He lifted my skirt and pulled my pantyhose down to my knees. He began kissing and licking my smooth inner thighs, occasionally lifting his tongue up to my crotch to dot it and get it wet through the panties. It drove me absolutely insane to have a man between my legs licking and kissing. I put my hands on the back of his head and tried to thrust him into my crotch. He resisted somewhat, slapping my ass pretty hard and picking me up to put me on his bed. My pantyhose had fallen down to my ankles. He pulled them off my feet and used them to tie each of my arms to the headboard of his bed.

We were all talk earlier in the evening, but now there wasn’t much to say. It was time to fuck. He would kiss me before and after each move he would make on me. If he was fingering my ass, he would kiss me, if he caressed my tits, he would kiss me. He really got me relaxed. His wife emerged from the bathroom in a red satin babydoll nightie with a red satin thong underneath. As she approached the bed Harry stood up and began caressing my legs. I was so loose. Tawni laid down next to me and we began to kiss. She told me I smelled good. I told her she did, too. We kissed and felt each other up while Harry massaged his fingers into my man pussy. No soonee than I could get my breath from making out with Tawni, Harry had my legs totally spread, pushing my panties off to the side and sticking 3 fingers in my asshole. Tawni straddled my face with her legs and pulled her little thong out of her pussy. She fondled my hair and cheek bones as I began lapping at her moist center. She was grinding her pussy into my mouth, rubbing her clit on the tip of my nose as she thrust her pussy as far into my mouth as she could. She was gushing juice. Harry had my legs spread and my ass begging for his cock. He came up to kiss his wife while sticking his dick in my mouth, getting it wet and stiff. Harry went back down and immediately stuck his dick in me. I was so hot that it didn’t take the normal easing into. My pussy was ready. Harry slid right in.
“Hold your legs up, Sweet Bitch Ashley,” said Harry, so he could free his hands to rub Tawni’s tits.
I held my legs as far as I could spread them, lapping at Tawni’s pussy, feeling Harry get fully into my asshole. Harry’s hands were furiously squeezing Tawni’s tits and she was moaning, grinding her pussy onto my teeth and lips. I was being smothered in pussy juice, and was fighting for air from being fucked so deep by Harry. I could hardly catch my breath. I began to cum in my panties. Harry sensed it and rubbed my dick with one of his hands through my satin crotch. I was cumming at a nonstop pace, little bits oozing out with each pump Harry gave my ass pussy a rub from the top and made me sliver in pleasure. I was eating his wife’s cunt furiously and writhing around in my own pleasure while he thrust repeatedly into me. He got his cock in deep, kept it there, asked his wife to move her position, and he began to kiss and stub fuck me. Just as I had imagined. My legs were spread on their own now, as he began to fuck me tightly inside my hole. I began to cum again. He was fucking me so good that my cum was temporarily nonstop. I was spurting a little shot of cum with each thrust he made into my hole. He began working furiously to his end, now his thrusts were long and deep, he was breathing heavy, saying, “Oh yeah, Sweet Bitch Ashley, I’m gonna cum!” He thrust harder and harder. I was cumming non-stop, my ass and crotch numb from endless sensation. He pulled his cock out, yanked the rubber off and ran up my body to put his cock in my lips. I grabbed it with my lips and sucked while it exploded into my mouth. I gagged a little, got my composure, and proceeded to take every last drop of cum down my throat. Tawni was licking Harry’s balls, making his cock throb in my mouth, draining every last bit of cum down my throat. I could hardly breathe. I was still moaning after he got off me, just moaning and rolling my eyes back in my head. Tawni kissed my lips, and Harry lay down between us, kissing us each on the forehead and rubbing my chest and playfully fixing my hair that was seriously messed up. We had a glass of wine, not saying much, just touching one another, and smiling. I had cum so much that my panties looked like I had been in a bathtub. The satin clung to my sticky soft cock, and cum dripped from the crotch. I pulled my pantyhose back up, reapplied lipstick, gave them each deep long kisses goodbye and I went on my way. Upon arriving home I jerked off again, taking a dildo and ramming it my pussy while I yanked my cock until it exploded again. And that, my friend, was Ashley Sweet Bitch’s best fuck ever! Kisses!