Surprise!

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Transexual Fun.
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It has been a couple of weeks since my last encounter, school is going well as is work. After school this afternoon I decide to grab myself a coffee and sit down to read through my homework assignment. After just a few minutes a handsome young man asks if he can sit at the table in the chair across from me, I have no problem and tell him to be my guest.

After several minutes he asks "excuse me but do you know a girl named Ashleigh?"

I am a bit taken aback because very few people know of Ashleigh and that I am her, so I respond "no, I do not know her."

"Are you sure, you look a bit like her so I thought you might be related," he says.

"I am sure, where did you see this Ashleigh that would lead you to believe I know her?" I ask.

"Actually I saw her on a porn search site" he says.

"What? What are you talking about, but no I do not know her" I proclaimed.

"I am sorry" he says, you just look a little like her. I am sorry I asked."

"Well I am sure I do not know anyone you can find on any porn sites, is this some type of pick-up line? " I asked him.

"No, I really just thought.." he stammers "but here take a look at this."

He takes a tablet out of his back pack and browses to a site then plays the video, he forwards to a specific time in the video and pauses it.

"See, you have to admit she looks similar to you" he says.

I take a look at the screen and oh shit there I am, a cock penetrating my ass and another in my mouth. The view is from farther away in the room so you cannot definitely tell it is me but you can see that I am similar. I am a bit stunned that this video is apparently out there for the world to see, I look at the number of views and it is in the tens of thousands. I try to not let it slide that she is indeed me. I am a bit aghast that my business is out there for all to see.

"OK, I admit she does look similar to me but she looks like a lot of people" I say. I touch the screen and move the movie forward to a point where you can see my own little cock. "She is not even a normal girl."

"I know" he says "that is part of what I like about her and what made me think you are her."

"Well" I say "I do not know this Ashleigh double penetration girl."

He puts the tablet back into his backpack and says "well if you happen to meet Ashleigh can you give her this." He pulls out a sheet of paper and writes his name and number on it and hands it to me. He then stands up and walks away.

I watch as he walks, I guess I didn't pay attention to him when he sat down but he is very very tall . A tall dark young man, with a lovely ass. I look at the paper and read the name to myself, Christopher. Well Christopher I am not sure if Ashleigh will respond, but maybe. .

As I fold the paper and put it into my bag April walks up and says "Hi."

April works at the store with me so we have hung out at the mall a few times, she is a bit older than me - maybe mid 20s but very attractive.

"How are you doing today?" she asks.

"I am doing pretty good, just had an odd encounter but am thinking about maybe getting together with them."

"Well that sounds promising" she says "do you work tonight?"

"No, I am off today but work tomorrow and Friday" I reply.

"Me too, guess I will see you there" she says as she walks off.

I finished my coffee and head back to my room for the night where I completed my homework and then as I tried to fall asleep couldn't help but focus on and wonder if I should contact Christopher or not.

The following day I wake and get ready for school, after classes I head to work a little early so I can grab a coffee before starting. At the coffee shop I run into April so we sit down together with our coffees. We spend some time with small talk, hows your day etc. when she then asks if I ever called back my secret admirer, it takes me a minute to put two and two together but eventually I reply "I have not called him back, I am not sure if I should."

"Him?" she asks.

"UUUmm yes, him" I stammer into my reply.

I am not sure if I should explain further, I don't want my personal life to be public. I continue my answer "but I would rather not talk about it."

April looks at me and says "it is OK, I do not have a problem with you if you like men and I won't tell anyone. But you should reply to him if you are interested, I am sure he would like to hear from you."

I change the subject and fortunately we have to leave together to get to work on-time, so we leave the coffee shop and head to the store.

"You should at least text him" she says before we part ways and go to our own departments.

Through he night I keep thinking about my dilemma, should I text or not? I take out the paper and add Christopher as a contact on my phone and plug in his number, but cannot get up the courage to text him. By the time I take my first break I think I have mustered the courage to send him a text.

"Hi Christopher, this is Ashleigh. I hope U are well and will hit me back" I enter in my phone and after a few minutes I hit SEND.

After just a few minutes I get a response "Hi Ashleigh, I am glad you contacted my - I really want to meet you."

We continue to text back and forth through the night and into the next day where I eventually agree to meet Christopher Saturday night. We continue to text and familiarize ourselves with each other, I find out about him and what he likes and dislikes, I find out a bit about his past and who he is and who I should expect for our date, I also get some personal details like he is 6'10" tall and of mixed race.

At work on Friday I take a break and go to see April, who works in the makeup department. When there I drop hints that I am going to be seeing Christopher by asking if she had any makeup suggestions for me 'cause I have a date.

"Good for you" she says "and yes I have some makeup kits that would work for you. But have you ever put on makeup for yourself?"

"I have not so I might have to practice tomorrow before my date" I say.

"If you like I can come over and help you our" she says "I am free tomorrow afternoon."

April always looks good in her makeup and I am comfortable around her and she already knows about Ashleigh so I accept the offer and make arrangements to have her come over about 5 o'clock when we can do my makeup and hang out together. Now I just have to figure out what I am going to wear, I have several outfits from other encounters in the store but am missing some things I think I will need. So I head into the womens section to look around. My break ends before I can get what I need so I plan on coming back Saturday morning to pick up a few things before April comes over.

Saturday I awoke fairly early and headed straight to the computer to search for an outfit for my date later that evening. I figured that I can find what I need ahead of going to the store which would make it easier to gather all that I needed. I put together a wish list, took a shower and was getting ready to go when I heard a knock on the door. Not expecting anyone I looked out the peep hole and low and behold there was April hours earlier than I expected. I opened the door to greet her.

"Good morning sunshine" she says "how are you doing, are you excited for tonight?"

"I am good and yes I am excited, you're early though" I reply.

"I know, but I thought we could go to the mall and shop together, that is not what you are wearing is it?" she says.

"It was what I am wearing to go shopping, is there a problem?"

"Yes" she says "they are boys clothes, and you are a girl! Do you have anything you can wear now?"

I showed her what I did have and she said "put this on and I will do a quick makeover before we go."

I put on one of the dresses and panties I have, she makes some quick changes to my hair and puts on some lip gloss for me and we are off to the mall. We spend several hours there going from store to store trying on clothes, I model then she models and many times she comes into the changing room with me while I get undressed. It was a very fun and exciting day and we are able to find me a date outfit, plus we found some things to address other issues. First, I looked better in most dresses with a little up top so we bought some breast enhancers which gave me a little definition up there. We also found that in some cases there was definition where there shouldn't be, my little cock was visible at times so we found some spanx like panties which helped keep it under control. Once we had everything we headed back to my apartment to get ready for the night.

Back at the apartment April says "you should jump in the shower and get ready for the night. Be sure you shave like a girl."

I agreed and headed to the shower. In the bathroom I undressed and jumped in the shower, washed my hair and body then turned off the water to shave my legs, arm pits and crotch. I started with my armpits, then moved on and was lathering up my legs to get ready to shave them when I hear April ask "are you having your lady parts yet?"

"Not yet, working on my legs" I reply.

Next I hear April again "well I can help you with your cock and ass."

She sounded like she was in the bathroom so I peek around the shower curtain, there she is bent over her hair cascading down her back she is pulling down her panties and stepping out of them.

"I am not sure about this" I say "I am not interested in girls April."

She stands up fully naked and turns towards the shower and starts moving forward. She has lovely smaller tits and to my surprise a small bouncing cock is present.

"Surprise!" she says. "Hurry up and finish your legs and I will help you with your ass."

I finish shaving my legs and any random chest hairs and then April gets in the show with me.

"Bend over" she says.

I bend over and she lathers up my ass and shaves my cheeks and crack, as she finishes my ass hole I can feel her finger enter slowly and then pull it back out. Chills run up my spine as it feels so good. She then tugs on my cock through my legs, playing with it as it hardens. I turn around as she stands up, we are about the same height so our lips meet as we face each other and we start to make out. Our hands run across each others bodies, her tits press into me and our hard little cocks touch each other. She grabs my ass and pulls me closer as our tongues and cocks intertwine.

She then steps back, takes me by the hand and guides me out of the shower, out of the bathroom and into my bedroom. We lay down on the bed and continue to explore each other with our mouths and hands. I've never felt titties before so it is a new experience for me, she is about a C cup I think and I cannot help but play with her pretty little nipples with my fingers and then explore them with my tongue.

"They are fake" she says "but I love them."

After making out for a while on the bed she has me turn over so that I am laying face up and she swings one leg over and mounts me facing away. Her ass is so lovely and she lifts it off my stomach and moves it back towards my face, I can feel her cock as it rubs up along my flat chest leaving a trail of pre-cum along its way. She backs up until her cock reaches my chin and then the starts to play with my already hard cock. I decide to do the same and use my tongue to play with her cock working it into my mouth as she begins to bob up and down on mine. Her cock is small like mine but feels wonderful as my tongue circles the head and licks her cum leaking slit. I reach up and around her to squeeze her ass cheeks while I can feel her tits bounce against my stomach as she makes love to my cock.

I move my hips up and down quicker and quicker as I cannot keep from cumming any longer, I shoot my load into her mouth as she grips my cock with her lips to take in my load. As my cock twitches emptying into her mouth it becomes more and more sensitive, it feels so very good.

Once my cock is empty I roll over on top of her and use my mouth to lick and suck her cock. Her cock feels so warm and wonderful in my mouth, I bob up and down on it until she cums, accepting and swallowing her completely.

After we have both cum we snuggle up to each other and lay there for a while, gently touching and caressing each other until we fall asleep in each others arms.

After a quick nap I can feel April nudging me saying "Wake up, we have to get you ready for your date!"

I put on my panties and bra as does she and we head into the bathroom to get me ready for my date where April starts with my nails, she glues on finger nails and then paints them and my toenails a lovely ping which almost matches the undies I am wearing. She then she does my hair, she teases it, parts it, curls the ends and and puts in product before starting my make up. It takes her a while to put on my makeup, she gently works on me and I let her do what she feels is best for an evening date. I am facing away from the mirror so I cannot see what she is doing, I can just feel her gentle touch as she works on my face and eyes, she keeps saying "you are going to look so good"

Once she is done we go back to the bedroom and put on the clothes we bought for tonight, I am wearing a short pair of white socks w/lace trim under a pair of 4" heels w/ankle strap. I have on a black, white and grey plaid pleated mini skirt, mid thigh, with a pair of pink spanx bikini panties under them to keep things under control. I am wearing a pink lace bra with my breast enhancers in (giving me maybe an A cup) under a white button up blouse so you can see the bra through the material of the blouse. When I look in the mirror I am astounded at how I look, the smokey eyes and feminine hair along with the sexy outfit.

"Good luck tonight" she says "I think you will get lucky!"

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  • COMMENTS
1 Comments
BrendaNWBrendaNWover 4 years ago
Lucky girl

I know Ashleigh is going to get lucky on her date 😘

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