Jackie’s First Night as a Completed Woman

by: Jackie Edwards

 

I am Jackie. I am a thirty-something crossdresser. This is the story of my first sexual experience as Jackie.

As my male self I was a very conservative Manager for a very large corporation headquartered in the San Francisco Bay area. There was no way I could come out at work so I limited myself to going out as Jackie after work, I would go to restaurants and bars in the bay area and was having a great time. I joined a couple of TG organizations in the area and found some great friends.

One evening I was going to a social gathering of a CD/TV group in Walnut Creek. After work I grabbed a snack and then went home to prepare for the evening. I shaved my face very closely, used a popular hair remover on the rest of my body and then took a long hot bubble bath. After I dried off I went about applying my make up after which I put my bra on and inserted my C cup breast forms I then put on my tight fitting gaff that flattened my "clit" and gave me a feminine front. I dressed in a new outfit I had bought the previous day. It was a denim outfit with a mini skirt and short jacket. With it I wore a white scooped neck t-shirt, my tan nylons with a pair of short white boots with 3 inch spiked heels. I put my large gold hoops in my pierced ears, my gold heart on a chain around my neck and my several fashion rings on my fingers. I am sometimes a blonde and sometimes a redhead. I decided that I would wear my long and curly dark auburn wig that night. I attached my glue-on nails and painted them the same bright red as my lipstick. I then sprayed on some white diamonds cologne, fluffed my hair and was ready to go.

I arrived at the bar where the group was meeting and met several friends. I was getting a fresh drink from the bar when I noticed a couple of girls come in the bar. THEY WORKED IN THE SAME OFFICE that I did. We were not friends, but they would know me. As I was about to panic one of them looked straight at me and I noticed that they didn’t recognize me. Throughout the night I found out that they knew one of my CD friends and also that they were lesbian lovers. I became bolder with that information and started talking to them. I finally told them who I was and they could not believe it. As we talked they said they wanted to go out with me the next week. I asked them if they had ever been to the Mother Load bar in San Francisco. They told me that they had never been there and I explained that it was a bar where all the TV/TS hookers hang out and there were some beautiful girls there. We agreed to go there next week.

The Following week after work I went through my usual routine to get ready. This night I would be a blonde. After applying my make up I put on my micro-mini leather skirt with my v-necked pink sweater and 4 inch black heels. I called the girls to see if they were ready and Carol said that Ann was ready but she couldn’t find anything to ware. As we were about the same size I told her that I would bring her a dress of mine to wear. I asked her if she had some black heels and she said yes. I grabbed one of my "little black" dresses and started to their apartment. I gave Carol my dress and she went to put it on. When she was ready we left for the Mother Load.

We arrived, went in and had a couple of drinks as we watched the "Girls" come and go. There were the usual numbers of admirers there also. Ann asked me if I had ever turned a trick there and I told her "of course not". They both asked me if I had ever been propositioned there and I said yes, many times. They then told me that I should accept one of the offers. I said no, but they kept badgering me. Throughout the evening they kept telling me that I needed to feel what a woman felt even if I just gave a blowjob. Carol said if I would accept that they would let me be the third girl in their bed that night. I still wasn’t completely convinced. Then a gentleman sent us all drinks with a note that said "will one of you special ladies care to keep me company for a while?" Well Carol and Ann said that I was the only "special lady" so I should respond. I was thinking fast and decided that if I priced myself too high that he would decide to ask someone else and I could still say to Carol and Ann that I tried and qualify for Carols offer. I went over and sat down by the gentleman and asked what he had in mind. He asked "how much for a blowjob?" I whispered that it would cost him $150.00 with me. To my surprise he said, "OK where do we go". I was caught now so I told him in his car and away from here, but he had to bring me back. He said, "OK" and got up and took my hand and we started out the door. I looked at Carol and Ann as I was leaving and they both gave me the thumbs up.

When we got in his BMW he asked where I wanted to go so I told him to go down by the bay. As he was driving I could tell he was more nervous than I was. I looked and saw he had a wedding ring on and asked if his wife gave him blowjobs. He said "no, never". When he stopped I said that we might as well take care of business first and that I only worked with a rubber. He said fine, opened his wallet and gave me the $150.00 and he even had a rubber in there. I started rubbing his thigh and kissing him on the ear and he was ready in no time. I unzipped his fly and reached in. His cock was about 8 inches and about 2 inches around. I rolled the rubber down his shaft and started by kissing my way form the tip to the base. I licked the underside a few times as he moaned with pleasure. As I took as much of his cock in my mouth as I could he yelled, "Suck it Baby". I pumped up and down a few times and felt him come inside the rubber while he was in my mouth. I slowed my pumping and licked the shaft a few times and asked him how he liked it. He said he wanted to see me again and get a repeat performance, I told him that he might catch me again at the Mother Load and asked him to drive me back.

I fixed my face as we drove and when we got back he dropped me at the door. I walked in with a grin on my face and Carol and Ann started clapping. I’m sure my face was crimson. I told Carol that I lived up to my half of the bargain and she agreed. We went back to their apartment and as we came in Carol told Ann to get me one of her baby dolls to wear to bed. I left my nylons, bra and "breasts" on and put on the nightgown. Carol sleeps in the buff, I found out, and Ann had a nightgown like mine in a different color. We all started kissing feeling and rubbing each other and Carol said that I couldn’t enter either one of them, but had to make love as a girl. I reluctantly agreed. We went on for about an hour humping and rubbing and licking and kissing. I was in the process of eating Ann’s pussy and I lost track of Carol when I felt something touch my ass hole. I looked and saw Carol with a strap-on cock, she told me to keep on with Ann and she would be very gentle. It was hard to concentrate on giving Ann a good time as Carol was pushing harder and harder so Ann turned around slipped under me and started sucking my 6-inch "pussy". Carol continued and soon was in to the base. It hurt like hell as she was going in but with Ann on my "pussy" it was bearable. As Carol started pumping my backside Ann was pumping my front side. I cam as I had never cum before, it was the most intense orgasm I had ever had. When I recovered I nibbled on Ann’s nipples as Carol did her with the strap-on. After Ann came I went down on Carol as Ann played with her breasts. We didn’t get much sleep that night. But I felt more like a woman than I ever had and was $150.00 richer.

 

 

 

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© 2002 by Jackie Edwards. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.