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One friday night back when I was 25 I was in the chat rooms looking for a little action. I had chat with a few ladies that got me nice and hard,but no of them lived in the same city as me and i was looking for more hands on fun. At about midnight a message popped up. "Hi I'm DeeDee whats your name?" "My name is Joe." I respond. "Hi joe how old are you and where are you from?" She asked me. I tell her my age and where im from. She tells me where she is and its not far from my place. So i ask"How old are your and what are you looking for tonight?" Hoping to get some action.

She responded with"I'm 35 m crossdresser,I'm very passable." "I even get hit on when i go to the clubs." I didnt know what to say, I have fantasied about sucking a mans cock,but never had the nerve to do it. I sat there for a few moment not knowing what eles to say. "When he responded with"Did i scare you off sweety?" At this point I became very shy. "No" Was all I replied. "Are you bi honey?" He asked me. "I have been curious." "What have you been curious to try?" "I what try to suck a dick." "Well honey I have nice one for you under my skirt." "would you like to see it?" Nervously I respond. "Yes." "Then whats your address sweety and I'll let you see it."

I'll said."I dont know I have never done this before." "It's ok to be nervous sweety everbody is ther're first time." "I promise I'll be gental and you dont have to do anything you dont want to do." Still shy I tell him. "I dont know." He said. "Well I know your horny so how about I bring over a porn movie we can watch it then you can just sit back and let auntie DeeDee take care of you." "You wont have to do anything just sit back and let me service your cock." "I guarantee until I show you my cock,you'll sware Im a woman." Being as horny as I am,and the fact that I havent had a blowjob in a while I agreed and gave him my address.

I log out shut off my pc. I turn out all the lightes.I have some Chrismas lights around my livingroom ceiling,it gives off a nice ambient red glow thats perfect for watching movies or getting a bj.I sit down on my couch and Pull out my cock. I start stroking thinking about the bj I'm going to get. But then my mind wonders to his cock, and I sware my cocks gets even harder. I'm thinking I'm going to do it.I'm going to suck my first cock. So here I am sitting on my couch stroking my cock thinking of the dick I'm going suck. How big is it?Will it have any hair?What would it feel like in my mouth?How much will he cum? Where is he going to cum? I have tasted my own cum before and didnt care for it,I dont think Im ready to taste another mans cum.

And at that point I hear a gentle knock on my door. Oh fuck this it it! "I'm thinking to my self. I tuck my now throbbing boner back into my pants,and get up an answer the door. Jaw dropped when I opened the door. There he stood about 5'7" black knee hight socks,short red plaid skirt the stopped right above the knees,White button down blouse. long streight brown hair that went just pasted he's shoulders. I know the school girl look was a cliche but hell it worked for me. He even had on a pair of pink starter hightops that just made the outfit look cuter. With this sweet little sexy feminine voice he saids. "So are you going to stare at me all night or are you going to let me in?"

As he walks past me I close the door behind him. He puts down his purse and stikes a pose,hands on his hips legs close with one knee little bent over the other. tilts his head slightly to the side and saids. "So what do you think?" I was dumstruk, I was expecting some guy in a crapy wig and bad make up. "Wow your hot!" I you sure you not a real woman?" With a smile on his face he comes in closer and whistpers in my ear. "I guess you'll only know for sure when you ready." He gave me a pec on the cheak and with a wink of his eye and a giggle he spun around and went over to his purse.

He pulled out a dvd and when he bent down to put in in my player his skirt rose up and i caught a glimps of his ass,he had a cute little heart shapped ass with white and red stripped cotton panties. As i was stareing at his ass all i was thinking was."Oh my god what have I gottin myself into?" He sits down on my couch closses his legs and pats the cushon next to him. "Come sit down sweety" I walk over and sit down next to him. He presses play on the remote and the movies starts.It starts out with these two hot chicks and a guy in a hotel room.the first girl is white looks to be abour 5'4' short skirt samll tits,the is latina little shorter than the other girl hot little shorts that hug her cute little ass,tits alttle bigger then her friends.There topless and there making out with the guy.there kissing and petting,and rubbing eachother alover. then the girls get him on the bed remove his pants and start sucking him off. The useaual porno stuff.But then the girls pull down the bottoms and the both have hard little dicks,and the guy began to start sucking them both off. Oh my god he put in a tranny porn.

I look at him and he is staring at my, I guess he wanted to get my reaction. He gives me this sexy smile and winks at me. "Keep watching sweety it gets better." As i watch this guy have hot sex with these two little trannies I cant help but get turned on. After several minuits of watching he leans into me and whispers in my ear. "Do you like what you see honey?" And puts his tongue in my ear. A shiver goes down my spine and i moan. "Oh god yes." He giggles and kisses me on the lips.As he slides his tongue in my mouth,his hand finds it way onto my cock. His lips are so soft,he even smells like a real woman.

He pulls up my shirt and sucks and nibbels on my nipples. "UUHH" "That feels so nice." I moan to him. He stradles me and puts his tongue in my mouth again. I grab his soft ass under his skrit and I give it a good squeeze. You have a nice ass." I tell him."Thank you I run and swim alot." He tells me and puts his tongue back in my mouth. After a few moments of making out he breaks off the kiss. "MMM now just sit back relax and let auntie DeeDee take good care of you." He said as he slid off of me down to his knees between my legs.He unbuttons my jeans and slowly unzips them. My shorts are wet from precum. "Now lets see what you have for your auntie." As he takes hold of my wastband and pulls my shorts up and over my throbbing cock. "MMMM" "Did I do this to you or the movie?" "The movie just got me started." The rest was all you." He gives me that sexy little giggle and sucks my cock into his mouth.

"Oh yeah suck my cock you fucking slut!" This has got to be the best fucking blowjob i ever had.better than any woman has given me.I run my finger through his hair and hold onto the back of his head.As his head is bobbing up and down I can realise that this is no wig. He is playing with my balls and even rubs his fringer on my asshole. As im getting close to cumming I'm thinking is there really a cock under that skirt? If so I want to see it,I'm ready to suck it.

I look down at him and pull his head up."UUUUHHHH" I im getting close i need you to stop!" He looks up at my with his sexy eyes. "Whats the matter sweety?" "I want to do you now." I say to him."You sure sweety?" "Yes I'm ready for my fisrt cock." We get up,I take off my pants,and shrit.And she takes my place on the couch,slouching down so his butt is just on the edge of the couch.With his legs together he slowly runs his hand up his thighs and pulls up his skirt. "You ready sweety?" He tells me. I slowly nod my head. "Ok sweety here it is."

He places his hands on his knees and slowly slides them up between his thighs,spredding his legs apart. I could see the bulge in his panties. He grabs the crotch of his panties and pull it to the side pulling out his cock.It;s semi hard and and already like six inches and cut. "You want to touch it baby?" I put both my hands on his legs and Slide them up feelling how soft and smooth they are.He must use lotion on them every day. I slowly take his cock in my hand. Like his legs there is no hair on it. I wrap my fingers around it and slowy stroke it, I can feel it getting harder it my hand. It has to be a good 71/2 to eight inches! I stroked his cock up and down getting a good feel for it. "MMMM that feels nice." He moaned with that hot sexy fem voice of his.

I get my face closer to his cock. This is it, I'm going to get my frist taste of cock.I am so nervous,my heart is pounding as I get closer to his cock. I look up into his eyes and he gives me a sexy smile,runs his fingers through my hair and saids in a low sexy voice. "It's ok sweety,take your time." I've never been so hard,my heart is pounding so hard I feel like it mite explode. I will never forget the feeling of when his cock first touched my lips,my lips went pasted his head and half way down his shaft, I fell in love at that moment.I held his cock in my mouth taking amoment to feel it. I can feel his pulse of his heart as his cock throbbs in my mouth. I swirl my tongue around the head getting a good taste of it. I slwoly rise up to his head and back down his shaft. I get in a good rythim,as i bob my head up and down in his lap. He reaches out and places his hand on my back and rubs it up my neck to the back of my head and back down again moaning. "UUUHHH" "Oh yes your doing so good." "Just a little more sucktion baby." "MMMM just like that." This is so fucking hot,I am so turned on that my cock is dripping pre-cum into a puddle on the carpet. I have seen many women doing this to me and I finaly understood them. I'm inlove with cock!

"UUUHHH" "Your so good at this." "You sure you never done this before?" He asked me. I just shake my head."Ut-ah" and continue with my sucking. "Well your a natural honey." I just look up into his eyes and smile with his cock still in my mouth. "Oh god im going to cum baby!" "Do you want it in your mouth sweety?" I slowly pull his cock out of my mouth,and swirl my tongue around the head a bit. Stoking him up and down i look into his eyes and say." could you shoot it on my chest auntie DeeDee?"
He smirks and stands up,bends down and gives me a pec on the lips and saids. "Sure sweety" He has me lay on the floor flat on my back,then he straddels me just above my cock. My cock is rubbing the crack of his ass,soking his panties with my pre-cum. Kneeling he lifts up his skirt thrust out his cock and strokes if for me. "Oh god baby here it cums!" Just then his first shot of cum flies out and lands on my forhead,its a long string from my forhead to my chin. The second shot hits me in the mouth,the thrid rope is not as powerful and hits me under my chin stretching down just above my bellybutton.The last few drops making a puddle on my stumach. I love the feeling of warm cum shooting on my body. He is now smearing the puddle of cum on my stumach with his cock. He leands down and licks the cum off my mouth and kisses me.

"So sweety how did you like your first cock?" he asked me. I tell him."It was awsome and i plan to do it again." He kisses me again and asked."So stud you think you up to fucking my sexy little ass?" I decline."I'm sorry i dont think in ready for that yet." "It's ok sweety,when you are you give me a call." "I want to be your first for everything." "I may even top you when your ready." I just laugh. "Well I'm definitely not ready for that." He reaches back and feels my cock still rubbing his ass."Well It seems you are ready for another session with my mouth." He said.

He slid down between my legs and onces again I soon felt his hot breath on the tip of my cock. He raised my cock and captured my pre-cum coverd head between his lips. He began to strok his hand and bob his mouth,I was on the edge. He looked up at me and said. "I love your cock,I could do this all night." "I dont think I can take another minute of this,much less all night." With that he dropped his mouth down and slid my entire cock straight into hi throat. I nearly lost it as he began to fuck his throat with my cock. My hips came up as my balls contracted and I grapsed at the carpet and tried to hold back,but it was all over. "Oh fuck I'm cumming!" And let loose a blast of cum,a second huge spurt,a third,then a forth. I had never cum like this in my life,and he swallowed every bit of my cum,not letting a single drop escape his hungery lips.

It seemed like hours before i came down from my orgasm.He pulled my softening cock out of his mouth with a load pop.Came up to me and slid his tongue in my mouth,gave me a hard passionate kiss,and grabbed his purse pulled out a pen and with a giggle he began to write something on my now soft cock. when he was done he kissed my cock got up. "Thanks for the night sweety I had fun." And left me laying on the floor with my cock freshly sucked and coverd in his cum. I lay there thinking to my self this was the best night of my life. I look down to see what he wrote on my dick. It said call me anytime sweety and left his #. I run a finger throw his cum on my face and I put it in my mouth. and I say outloud."Oh you bet your sweet ass i will."
12 comments

Anonymous readerReport

2014-10-23 00:47:48
Very hot If that guy had been me I am afraid I would of let him fuck me.

anonymous readerReport

2013-11-09 03:14:01
loved the story, brought back some great memories for me too, only I was the crossdresser, and it was true for me as I write this.I now hav e a steady partner who was seduced by me, and we have the best sex since that first night. I didn't think a cock could taste so good, and even better when he came!

anonymous readerReport

2012-10-19 21:00:06
I remember my first cock, I remember sucking the head and pulling his hot shaft untill he spurted his hot massive load of cum down my throat and I swallowed all I could I was so turned on wen he finished I flipped my legs ova head n jerked my cock off into my own mouth till I filled it up. Yummy

anonymous readerReport

2012-10-19 20:53:46
That story was hot but ur rite I would've eaten that huge load of cum too or got him to fill my ass up

anonymous readerReport

2012-06-27 15:30:46
sounds like what im looking for when I have my first cock

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