Sissy's Adventures: Sissy's First Date

By Terri Leigh

A young crossdresser with the dream job of working as a stockboy in a lingerie store meets his perfect Alpha Daddy online, and SUPRISE, he only lives across town. Join our little sissy as she endures lots of sexy adventures along the way for her first date with her perfect man, including a chance gloryhole adventure in a downtown adult bookstore...

Excerpt:

Watching the video I was barely aware of the man's hands fondling me through my sweats. He lifted my sweatshirt over my head revealing my naked chest, and started playing with my nipples. He then slowly guided my sweatpants down and coaxed me out of my shoes and sweats. Once again, barely conscious of what I was doing I was half naked again, and this time in front of a man who I'd only met once. All of a sudden it dawned on me what was happening. I turned to him, fear in my eyes and voice, and told him that I couldn't do this; I was saving my virginity for Jerry. I then confessed and explained everything to him. Fearful that I was going to get beat up or raped, I was wrong. This man could not have been nicer about it. He just asked if it was okay if he fondled me while I watch the videos. I had never had anyone else touch me the way he was touching me, so I leaned in, standing in my panties and thigh high stockings, and hugged him, telling him I would love for him to keep touching me like that, and that it felt wonderful.
He continued fondling me as I looked up into his eyes. His eyes were filled with lust, he wanted me, and I loved that feeling. But he was very nice, asking before he was touching me, all the while asking if I was still okay. And then he asked the big question. "Can I take my cock out of my pants?" He asked. Of course I said yes. He unzipped and pulled out a nicely shaped, about 6 1/2 inch cock, with a little helmet shaped head. He started stroking it and then took my soft delicate hand into his, and wrapped my hand around his cock.

• Language: English
• Publisher: Terri Leigh
• Release date: Apr 29, 2012
• ISBN: 9781476069241

Terri Leigh

Youthful author and publisher of alternative and obscure erotica!Many stories are true, others are taken from true events.Enjoy!

Book preview

Sissy’s Adventures – Sissy’s First Date

Terri Leigh

Copyright Terri Leigh 2012

Published by Hunnydo Publishing at Smashwords

Sissy’s First Date

I nervously got out of my car, trembling in my high heels, and looked up the long cobblestone driveway to the beautiful brick house. It wasn’t quite a mansion, but it was bigger than any house around town. Secluded from the road by large cottonwood trees, He promised there would be lots of privacy for us, and now, I was too was convinced.

I closed the door to my girly little sports car, straightened my miniskirt, flattened out any wrinkles in my blouse, and adjusted my stockings. I dropped my keys in my purse, and quickly grabbed my compact mirror to make sure my makeup was perfect. I was satisfied with my hair and makeup, so taking a long breath to settle my nerves; I walked up the cobblestone driveway and walkway.

Having worn high heels indoors mostly, I found that the uneven surface was a bit harder to walk on than imagined. I carefully and purposely took each step slowly and deliberately. What a sight I must have been, placing each foot directly in front of the other, wiggling my hips to maintain balance, and making my miniskirt covered ass sway rhythmically back and forth…lol

I traversed the long walkway successfully, and was at the large chestnut French doors. I took another deep breath, and extended my right pointer finger, with my long as lacquered nails glistening in the evening light, and rang the doorbell……

I should probably jump back a bit and tell you a bit about myself, and how I got here, and who I am coming to visit…

Hi my name is Terri. I am a 19-year-old cross-dresser. I have been dressing for about five years now. First I started dressing in secrecy, taking my sisters or mothers panties and or lingerie into the bathroom or and my bedroom and playing dress-up. I moved out of my parent’s house just over two years ago. Since then I have taken every opportunity to dress up when I'm not at school or work. I have accumulated quite a wardrobe of high heels, panties, lingerie, dresses, miniskirts, etc...

I should mention that I work as a stock boy at a lingerie store at the mall. This gives me the great opportunity to see all the hot new merchandise as it comes in. Having time alone stockroom also gives me a chance to try things on with very little chance of being caught. I get a great discount, and always tell the girls at the counter that I am buying things for my girlfriend, but I think a couple of them suspect my secret.

Every night when I go home, I love taking a long bubble bath, shaving off all of my body hair if needed, and getting dressed up in my silky, satiny, pretty things… I especially have a weakness for high heels, stockings, and garters. I love the way they feel on my legs, and make me feel so sexy. In fact, I love wearing stockings and high heels so much that I have been taking Pilate’s classes and yoga to firm and shapely legs to look very very feminine. I am about 5'6" in height just over 125 pounds. I have a very thin smooth body with lean long feminine legs. I have during a little body hair and have never been able to grow facial hair. Which is fine with me because the more satiny, and silky my skin feels the more feminine I look and feel. I have long dark brown hair just past my shoulders, bright blue eyes, and long pretty eye lashes. I have gone out in public dressed up in my pretty things, and have had no problems whatsoever. I consider myself to be a very passable, very sexy cross-dresser.

But alas, I have kept most of my cross dressing to myself in my small two bedroom apartment on the 27th floor. I would mostly just get dressed, make myself drink, and either pop in a DVD, or turn on my computer and watch various cross dressing videos, porn, etc. One night, after watching a very hot video of a very busty beautiful shemale giving a hot older man incredible blowjob, then taking his huge 9 inch cock in her tight ass bareback on my computer, an ad popped up for cross-dresser and shemale dating site. Now I had never thought before about dressing up for anybody. It was purely for my own enjoyment and sexual arousal. This ad sparked something in me, and now I really wanted to dress for a man who might appreciate a girl like me.

So I clicked on the ad, and started building my profile. The site was free for