A Night Out

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His exciting first encounter with a sexy shemale.
1.9k words
4.31
130.4k
30

Part 1 of the 4 part series

Updated 10/15/2022
Created 03/30/2007
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I have been a long time fan of Literotica but have never considered writing anything myself. This is my first story of any kind anywhere. I did not have anyone proof read it so sorry for any errors there may be.

I was at the bar one Friday night after a long, long week at work. It was one of these weeks where at the end you tell yourself you need a drink. I was still new to this town and haven't been out that much so I went to a bar near where I live in case I decided to drink myself into a stupor. I got there about 7 and went right up to the bar to order my drink.

Once I got my drink I took the bar in. It was more of a club then a bar, the type that late at night would be filled with drunken idiots dancing and grinding on the dance floor. The place was only a third full but surprisingly there were more than a few good looking women. A group of women caught my eye and I kept stealing glances while I sipped my beer. Now I'm not a bad looking guy but no where near confident enough to go up to and start a conversation with a group of good looking women.

There was a girl though who kept stealing glances at me and we both caught each other's eye more than once. She was a petite, exotic looking brunette, with brown eyes and dark skin. She looked like she was Asian or maybe Middle Eastern and she was just my type. This went on for about a half hour. There was a little giggling and looking in my direction when one of the ladies in the group came over to where I was sitting. She ordered another round for her table and then smiled at me. "My friend thinks you're hot" she said. I asked her which friend and she told me the girl I was playing eye tag with. I just wanted to tell you because she is the quiet type and it's not very often she tells us she likes a guy. I decided to take a chance and followed her to their table. Introductions were made but the only name I remembered was hers, Neerja.

She was shy at first as her friends talked and talked. They asked me about what I did and where I worked and gave me the standard replies. Neerja just sat there quietly and listened. I smiled and looked at her as I talked to show her that she was the one I was interested in and the reason I was there. They finally started to get the picture and I was able to steal her away from the group by asking her if I could buy her a drink. She quickly agreed and we moved to a small quiet table in the back.

We hit it off right away; she could be more herself away from the group and less one of the girls. She told me she was from India but moved to the United States when she was five. Her mother was from Thailand and her father was from Budapest. I loved the way she talked, she smiled as she spoke and I was totally smitten with her. We talked all night and I would have loved to take her home but I figured she was the shy one so I asked her for her number so I could call her sometime to go out. She said how about right now. "I'm having a great time and I don't want the night to end" she said. It was still early so I suggested we have a night cap at my place since I lived nearby. She quickly agreed and told her friends she was leaving and we were off. Her friends were giving me the thumbs up as we headed for the door.

We made small talk on the way to my place and when we got there she surprised me by nearly jumping into my arms and shoving her tongue down my throat. We were going at it pretty good when she suddenly stopped and backed away from me. She stared saying sorry, sorry, sorry, I don't know what came over me. I told her not to worry, I had the same idea in my head but I didn't want to move to fast.

We both got a good laugh out of that and then I leaned in to kiss her again but she pulled away. I have to tell you something. I stared to think that this girl might be a virgin or something like that but what she told me was much more revealing. I'm not who you think I am. I'm not the type of girl who just goes home with any old guy. To tell you the truth I haven't been with a guy in a very, very long time. It's not because I don't want to its just hard for me.

She looked me right in the eye and told me "I'm not like other girls, I'm different". I wanted to tell you before we went any further. In my mind I'm all woman but I was born with a "male" part. I knew right away that I was looking at a shemale. Now I've never been with a shemale nor do I consider myself gay but I couldn't believe I was looking at a guy. This was a woman, she was petite but had curves, and she was stunning and feminine. She was one of the best looking women I've ever seen.

I was curious so I asked her if she was comfortable with me asking some questions. She smiled and said okay, what do you want to know. First I asked how long she had lived as a woman, she told me as long as she could remember. She was born with a penis but looked so feminine that as she started to grow she was dressed as a girl. Then I asked her about her sexual past and she said she had been with only a few guys and a couple girls who were curious about a girl with a real dick and not some strap on. She said she started telling the guys about her part after a real bad experience with some macho dick head who started feeling her up and found her surprise. She told me he kicked the shit out of her and left her in the middle of nowhere with ripped and torn clothes.

I still could not believe that I was looking at a real life shemale so I asked her if she was comfortable showing me her dick. She smiled as said okay but that I had to show her mine too. "Turn about if fair play" she said. I agreed but suggested she go first. She nervously started to strip off her clothes while keeping an eye on me to gauge my reaction. She had really nice tits not to small but not very big either. Just the kind you would usually see on a small petite girl.

Her body was fabulous but what I wanted to see was what was under her skirt. She asked me to unzip her and I found that I was getting really turned on. I was starting to get hard as I unzipped her skirt watching her wiggle her hips to get out of her skirt. She had an amazing ass but she kept her back to me and wearing just her thong. "Your turn" she said looking over her shoulder.

I wasn't about to stop her know so I quickly shed my clothes until I was wearing just my boxers but I wasn't hiding the fact that I had a massive hard on. She turned and faced me and said "okay at the same time?" I nodded my head and we both lowered our underwear.

She had a small dick but it looked, I don't know; cute? She looked at my hard on and licked her lips. "Would you mind if I touched your dick" she said. Now I was really turned on and all I could do was nod my head. She stepped closer and tentatively touched my dick. She started slowly stroking my dick at first. It felt really good and I found my self wishing she would suck it for me. I was nervous about having a shemale suck my cock but I didn't really think of her that way. She was a hot, sexy, desirable woman who happened to have a dick.

She started stroking faster but then she abruptly stopped. She looked up at me and said "What are you thinking?" "Do you want to keep going?" I told her the truth, I was nervous but I know that I didn't want to stop. She smiled and said that she was glad I was honest with her. I told her lets keep going and she where it leads, we can always stop if either of us gets uncomfortable. As soon as I said it I knew I was in for a wild night.

She knelt down and started stoking me again, I was very turned on at this point and close to cuming so I pulled her up to me and kissed her hard. She returned the kiss with as much passion and we made the way clumsily into the bedroom. As we hit the bed we continued our make out session when I first felt her dick hit my leg. I wanted to get a closer look at it but before I could she slid down my body and smiled as she lowered her mouth on my hard cock.

She was fantastic, she worked her mouth up and down my dick as massaged my balls with one of her hands. She would bring me to the boiling point and then back off again. I was in heaven getting the best blow job of my life when I felt her fingers start massaging my asshole. I couldn't hold it in any longer and I emptied my balls into her mouth. She didn't back off rather lowered her mouth down to my pubic hairs and swallowed my entire load.

After word as I was basking in the afterglow of a fantastic nut I got nervous again. Was she expecting the same in return? She climbed up the bed and cuddled up next to me. I looked into her eyes and took in her beautiful face once again. She was stunning; I knew I wanted to explore this further. I opened my mouth to talk and she stopped me by putting her finger on my lips. "Let's just rest for a while." "You've been through a lot tonight and I really like you. I don't want to ruin what we have by you doing anything you might regret later."

It was like she read my mind. Then she curled up closer to me and we snuggled together until we fell asleep. I wasn't sure where this was going but I was excited to find out. When I woke up in the morning Neerja was gone but there was a letter on the pillow next to me with her name and number. It said that she had a great time last night and really hoped I would call her soon but, if I had second thoughts she would understand. I knew I would call her again because I really liked her, dick or not.

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7 Comments
SiamKittSiamKitt2 months ago

Wonderful little srory, & so believable.

This site is lacking these type of romantic tales nowadays (crossdressing & sissification has taken over on here).

Loved her shyness, loved his sincerity, loved the way they still enjoyed each other...Thank you for a story of almost love at 1st sight..Ring Neerja's number now...Then we all can enjoy pt 2.

ShortyMacShortyMacover 1 year ago

Such a hot sexy story, I’d love to meet up with a sexy sweet girl that that. It wouldn’t bother me one bit that she was transgender because I’ve been with several transgendered women over the years.

bambam4evrbambam4evrabout 11 years ago
Very nice

I thoroughly enjoyed this post, very nice start. I am looking forward to reading the entire series.

AnonymousAnonymousabout 14 years ago
Sweet and romantic.

Not your typical fare. A welcome change.

CymonCymonabout 17 years ago
Nice Story.

Enjoyed your story a lot, I liked how open he was and sensitive to her feelings.

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