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My First Time!

My first time with a shemale was one summer evening. For several months the city I lived in at the time a lot of transvestites, transsexuals, cross dressers and their admirers would hang out on forth street on Friday and Saturday nights. There were some really good-looking Ladies.

I had been attracted to shemales for years, but never was brave enough to contact one. So this was an opportunity for me to talk with a shemale for the first time. I would head for Fourth Street about nine, just as they would start to show up. About the third or fourth time I went there I met Christine, a very sexy African-American Lady. She was about 5'4" and 110 lbs beautiful brown eyes and a slender sexy body. She was wearing tight jeans and a zip front jacket zipped down far enough so I could see a lot of cleavage.

We chatted for a while and then I invited her to my place. She asked if I know that she had a little something EXTRA in her panties and said that I hadn't been sure but had thought so and was look forward to see for myself. I told her it would be my first time with a shemale. She then asked me if I was sure that I was ready for it. I told her
she could see for herself because it was easy to tell my hard **** was trying to get out of my pants.

Fifteen minutes later we walked in top my apartment. I fixed us some drinks and put on some music. We danced for a while; it gave me a chance to get my hands on her sexy *** as she ground her ***** against my now even harder ****. I unzipped her top and she let it slip to the floor and gave me my first look at her shemale breasts, they were small slightly more than an A cup but with large erect nipples.

I could hardly wait to get my lips on then, first licking and sucking one then the other.

Soon we were in the bedroom kissing and hugging as we undressed each other. Soon I was naked with my hard **** pressed tight to the crotch of her panties, which was the only thing she was now wearing.

Then we were on the bed exploring each others bodies I could not get enough of her nipples, just loved the taste. She whispered in my ear and asked if I was ready to see my first shemale **** and what did I want to DO with it.

Oh God yes, I was ready and said I would love to 69. It wasn't long before her panties were off. I couldn't wait to taste my first ****. God it was so good. I ran my tongue around the tip of her **** and then stuck the tip of my tongue on the tip of her **** tasting her precum. At that
instant I fell in love with sucking shemale ****. I now new I would suck shemale **** every chance I got. Next I took her small but rock hard **** into my mouth pulling it completely in. Sucking it long and deep into my throat savoring the taste of her sweet hard and hot ****.

As she also sucked my now raging hard **** I matched her every lick and suck of my **** making sure to give her as good of a **** sucking as she gave me. It was only a few minutes before we both were *******, spewing a load of hot *** into each other's mouths. Being new at sucking **** I
didn't swallow it fast enough and some dribble out between my lips and soon I hard *** allover my face. After she had sucked all of the *** out of **** and I out of her hot **** we turned around so we could kiss and lick our *** off of each others face, so I tasted hot only her *** but my own for the very first time. If I had know how much I would love sucking shemale **** I would have become a **** sucker years before.

It wasn't long before I had her legs over my shoulder so I could lick her tight hot ***-**** getting it wet and ready for my now again hard ****. I had not known how good a tight sexy ***-**** could taste. I licked and tongued her sweet ***-**** clean getting it ready for *******, soon I slide my **** slowly into her ***-**** feeling it tighten around my ****. **** her ***-**** hard and deep soon I could stand it no longer and shot my *** deep into her tight wet ***-****. After I slid my no longer hard **** out of her ***-**** I used my tongue to once more lick her ***-**** clean tasting her and my *** together.

She told me that she love the way I had ****** her ***-**** and was there any thing "ELSE" I would like to try? I told I would love to have her **** my virgin *** and she answered that she would love to be the first to **** my virgin ***.

Soon I was on my knees and bent over with my *** in the air anticipating my first *** *******. First Christine took some petroleum jelly from the jar on the nightstand and lubed my ******* getting it ready for her rock hard ****-****. At first she slowly slid her ****-**** into my tight virgin *** and then ****** my *** faster and harder. Soon she was pumping her hot *** deep into my no longer virgin ***.

God it felt so good, better than I had ever dreamed get ****** in the *** could feel.

We got together again a few weeks later and did it all again and it was even better than the first time. She mover away shortly after so I never so I never got to see her again.

SaraDoes SaraDoes 61-65, T 23 Responses Oct 24, 2009

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that made my panties o so wet

Hot story, I've been with a she male a couple times also, but still a virgin (at least with the real thing, been pegged and double donged about 10 or so times and loved that) but I did stole her and **** her. It is awesome

My first time was in Mexico, it was amazing!

Good times you slutty ***** **** suck ..I'm soo jealous of you ...you are my hero ...sd

Such a hot sexy story. It sounded amazing

I went into a bar in Milwaukee many years ago. There were some good looking women in there and I managed to pick a beauty out and we walked to her apartment nearby. when we got inside, we kissed and I started feeling here up and finally got my hand inside he panties. I was shocked to find a hard **** there. But WTF, by then I didn't care and we continued exactly what we were doing-kissing. We made out as if she was a female and I ****** her in the *** after she had sucked my ****. And I did suck her **** as well. a gear evening

Same here, hard as ****. Hot story!!

wow!! that has me rock hard

Thank you for your hot story I had a similar experience with a tranny escort but she did not **** me for pay she really liked my ex wife and I we used to make love to her when ever we could until she also moved away got I miss her so much!!

I would love to make my first experience as hot and sexy as your's must have been.

Hope it is! Every second from when I first wrapped my lips around the head of her **** until her last load of *** in my were fantastic!!

I loved your story and could only fantasize about it being me in the story. I've dreamed of being with a shemale or ts for along time and hope it come's true someday. Just like your's would be a dream *** true......

Wow, great story, thanks for sharing

Your first time sounded great. My first wasn't so spectacular, I was so nervous. But later on... check it out.

Mmm, every couple of weeks I get to go see a wonderful shemale. We've had some fun adventures. Makes me wet just thinking about seeing her tomorrow!

i missed my firstr chance to have a shemale. Her voice was so sexy and all. I chatted her up on the phone but when I went to meet her the address that I thought was hers wasnt. I miss understood her so that was the end of that. Never did get the chance again. Well maybe someday. Your story though was very nice. It made my **** go hard thinking about what you did.

Great story Sara.. It made me want my next experience very soon. My first was while in San Fran many years ago. It was so good.

Hope you all have had a chance to have two!!

Than you SaraDoes for your story, I found it very arousing.

i want to have it as till now i was only seeking

Sounds sooooo damn hot...**** and ****...a great combo.....<br />
<br />
<br />
Setting fantasies on high....;)

Lovely first time SaraDoes, thanks so much. I need to also have a shemale ****. Been a life long urge and dream and after reading your beautiful experience it has given me the encouragement to fulfill my dream. Thank you so much

ShannaB<br />
<br />
I hope your first time is as wonderful as mine was.<br />
<br />
SaraDoes

Honey,<br />
<br />
This was just the greatest story. I really enjoyed reading it, because it is so close to what I want to have happen to me. The way you committed to what you wanted and the way it all flowed, she being open to your emotions and whether you were ready for the next event, AWESOM. For the past couple months, I have been looking to find me me the Shemale, and i think I have. I called her. Her name is Sofia. HOT!!!! Anyway, your story has inspired me to make my move. I only hope my experience is your story hun.<br />
<br />
Lot o luv<br />
<br />
ShannaB