Finding My Genie Ch. 01

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Crossdresser finds a new girlfriend.
2.4k words
4.29
47.4k
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Part 1 of the 3 part series

Updated 06/07/2023
Created 12/05/2015
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jealouscuck
jealouscuck
2,572 Followers

It all started when I was 18 years old. I had been eyeing my older sister's lingerie for quite some time. She was the rebel child and I was the perfect one. Late at night I would slip into the laundry room and masturbate with her skimpy undies. This went on for a few months when one day Leah caught me. I thought she had tennis practice, but she missed that day for some reason. When I heard her it was too late. I just had time to hide my dick, but I was caught red handed with her panties in my hand.

Slowly she realized what I had been up to. She called me a creep and a pervert. She said that she was going to tell mom. I spent the whole week waiting to be punished or worse yet, counseled. That was one of the most miserable weeks of my life. Every time I saw her coming, I went the other way.

Finally one weekend my parents were away and I was staying with a friend and his family. My sister was supposed to be staying with her friend Beth. I had my friend's mother drop me by my house on Friday night to pick up my soccer cleats. Guess who was home; Sis, Beth and about ten of their friends. They had beer and pot everywhere. I went in, got my cleats and left. My friend's mom asked if the lights were on for a reason. I told her that my parents always left some lights on while we were gone.

The next week we made peace. She promised not to tell on me for using her panties and I agreed to keep her secret. We were always very close in a combative sort of way. My senior year in high school, I had a steady girlfriend Amber. One night we were doing some heavy petting in the den. Mom and Dad were gone and Leah came in and caught us. She stopped and talked and told stories on each other for awhile.

Leah then brought up the party she had while Mom and Dad were away. She said she sure was glad she had a get out of jail card for that one. Amber was sitting by me in her bra and panties under a blanket. She asked us to explain the hold she had on me. Leah lifted the blanket corner and told Amber to keep her panties on and not leave them with me. I turned beet red. Leah thought I was cool with that story, but when she saw my reaction she apologized to me and Amber over and over again.

I told Amber I would drive her home as it was getting late. She was puzzled by my reaction and tried to get me to laugh it off like Leah intended. I took her home and did not talk to her the rest of the week. I kept avoiding her at school and ignored her phone calls. Finally she caught me by myself Friday afternoon and let me have it about ignoring her. I told her that I figured she wanted to break up anyway. She was stunned and asked why. I assumed she knew exactly what Leah was talking about. She asked me what was so bad that I had to treat her that way.

It took parts of two days, but I finally told her more or less what had happened. She told me I was too sensitive and that she and her sister used to fuck each other with cucumbers and squash when they were that age. Finally we were making out in her car one night and she reached under her skirt and pulled her panties off. She unzipped my fly and began massaging my penis with them. I was a bundle of nerves but the thrill was too great. I started cumming as she held the panties firmly over the head of my cock.

Afterward she asked if I was over being embarrassed with her. This really brought us together and about once a month or so we would do that. One night she took my jeans and underwear off while she jacked me off. When it was time to leave, she boldly grabbed my low rise briefs and put them on. I asked what she was up to. She told me she had always wanted to swap underwear and now I could wear hers home or go without. I made a show of protesting, but in the end I was easily persuaded.

After panty trading became part of our relationship, I built up quite a collection. Every now and then I would take Amber shopping to replenish her lingerie drawer. She never asked for her panties back and she never gave my briefs back either. Amber and I dated for two more years before she moved to the east to finish college. Over time we met other people, but Amber is still special to me.

After Amber, I dated several girls in college, but never felt close enough to them. I had enjoyable sex with a series of girlfriends but never went beyond that. After graduation I got a job with a large architectural firm in Atlanta. There I was; new town, no girl and working my ass off to try to get ahead. I still maintained a limited stock of panties and I masturbated often late at night while wearing the frilly girl things.

One night I went out for an office party with some vendors. I decided on a whim to wear a pair of satin panties that I had purchased a few weeks before. I thought this would be a cut and dried affair and over by 9 pm. While there, I struck up a conversation with a pretty brunette who was there with her boss. She seemed about as eager to be there as I was. After dinner and drinks she suggested that I take her to a club she knew as a way of getting me acquainted with Atlanta I was very attracted to Genie as she was called by friends and family. We went in and had a few drinks and since she had come with her boss, I offered to take her home.

When we arrived, she asked me in for a nightcap. Maybe it was the alcohol or maybe we just hit it off but Genie was very outward and touching. She was very animated when she talked and laughed. As soon as we got there she went to her bedroom and kicked off her heels. She came back wearing gym shorts and a flimsy T shirt with no bra. I guessed her to be a D cup at least. Her nipples were almost poking holes in that T shirt. As we drank, she cuddled closer to me. I would have loved to have gone all the way with her but I knew she would see my purple satin panties. She even invited me to stay if I wasn't up to driving. She didn't want me to risk getting a DUI, she said. I even thought of going to the rest room and removing my panties, but that would seem strange. So finally I left. I felt so badly that I called her the following day and tried to make amends by telling her the liquor had given me a headache and I was embarrassed to say so. She told me not to worry, but seemed rather cool.

Weeks went by and finally I worked up the courage to call her. She was on her way out for a date and said she would catch me later. I was really upset because a liked her. She was gorgeous, smart, talented and sexy. Pity anyone who got out of her line. Pity me. Much to my surprise she called me the next Thursday afternoon at work. She asked if I was getting more settled, made small talk and finally just as she was saying goodbye, she asked why I didn't call her back the week before. I was shocked that she made this advance. I stumbled out an invitation to go to the movies Friday night. She asked whether she came by for me or vice versa. We went to the movies and back to her place.

This time I was dressed in male underwear but sort of bikini style. We seemed to pick up where we left off weeks before. As we kissed and fondled on her couch, she suggested we might be more comfortable in her bed. In the bedroom, I felt every inch of her body through her clothes and finally began unbuttoning her blouse. She had on a sheer underwire demi bra and a lacy thong. As she reached for my belt, I almost recoiled thinking back to our first date. She pulled my trousers down and complemented me on my taste in underwear. With my underwear still on, I laid her back on the bed, moved her thong to the side and began slowly licking, then sucking her pussy. I thrust my tongue into her moist vagina as she became more vocal. I brought her to a shuddering climax with just my tongue.

When she recovered, she rolled me over to return the favor. She likewise did not remove my underwear, but pulled my raging 6" cock out of the pouch and through the leg hole. She proceeded to give me the best blowjob I have ever had. I then made love to her for what seemed like an hour. The following morning she told me that she had wanted me the first time she laid eyes on me. When she got up to fix coffee, she picked up my underwear and again complemented me on how trendy and sexy they were. I thanked her and told her she had great taste in undergarments.

That was about all I expected about that topic, but we became very close rather quickly, not just sex partners, but also friends and confidants. We began staying over at each other's apartments most weekends. One Friday, we met after work and had dinner. Genie usually is a great planner, but she was preoccupied about work and forgot to pack a bag. We ended up back at my place watching TV and making love. She decided she wanted ice cream and I did not have any. She begged me to go get some and we finally did rock, paper, scissors to see who went out. I won. Even then she begged me to go with her but eventually pouted.

It was then that she realized that she had forgotten to pack a bag. I told her that was just a ploy to get me to go. She mocked insult and said she didn't play that way. However she was not going to put on her business attire so she raided my closet for some soccer shorts and flip flops. She added a baggy T shirt and mocked me as she left to run her errand. When she got back and we were serving up the ice cream, she had already kicked the shoes and shorts at the bedroom. We ate ice cream and watched a movie. Later, I began fondling her braless breasts through the T shirt. When we moved to my bedroom, I noticed that she had tossed her bra on my dresser when she had changed clothes.

As I fondled her breasts through the T shirt, it rose above her panties. She wore a pretty yellow thong. It was plain, but sexy as hell on her slender hips. I pushed my hand under the shirt and fondled her perfect full breasts.

I was always excited to touch her round boobs. I think if I had massaged them long enough, I would have cum without being touched. Her areolas were perfectly pink and sized in proportion to her lovely mounds. Her big nipples always got hard and poked through any shirt or bra that she wore.

The light was still on and I was about to turn it off when she stopped me. She said that she wanted to see me while we fucked. I removed her T shirt and almost came when those luscious breasts came into view. I fondled her again and sucked her hard nipples into my puckered lips. She had already removed my shirt and pants and now rose up to remove my bikini underwear. My hard cock plunged out as she slid my underwear down my legs. She reached for her thong, but I stopped her hand. I asked her to leave it on. She moved it to one side and mounted me. She began riding me like a wild horse as she leaned in and gave me tastes of her erect nipples.

We made love three times that night before falling asleep. We woke up about nine o'clock. We were both hungry. I told her that I would fix breakfast for her. After breakfast, Genie said that she was going to take a shower. She came back quickly and said that she just remembered she had not packed a bag. She said, "Since you insisted on fucking me with my thong on, it is all cummy." Then she asked if she could borrow a pair of mine.

I was now nervous for the first time. I told her to get in the shower and I would get a pair for her. I picked out a pair of traditional cotton briefs and gave them to her when she came out of the shower. She looked at them and then back at me saying, "You wear sexy bikini underwear and you want me to wear these old cotton drawers? How about you give me something a little more sexy?"

I nervously reached in my drawer and came out with a red bikini styled male underwear. Genie said, "That's better." She wondered aloud why I would want her to wear plain "tidy whities" when I myself wore sexy bikinis. I apologized and we had a good laugh. She observed that maybe I gave her the plain briefs because she wore such a plain thong. I told her that her bright yellow thong was definitely not plain. She said, "Just the same, when we go back to my apartment to get ready for dinner, I will be wearing something a little sexier for my new boyfriend."

jealouscuck
jealouscuck
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AnonymousAnonymousover 5 years ago
What happened?

I was expecting more crossdressing than that. But fun story anyway

AnonymousAnonymousover 8 years ago
Great start!

Hope this leads to more!

rdoolittlerdoolittleover 8 years ago
There must be more.

I hope you have another chapter (or more) since it ended without a satisfactory resolution. I enjoyed and will hope for more.

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