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My First Bi Experience and Crossdressing

At the time Kim lived in Houston and I in Dallas. She ran an ad in a local newspaper for a bi guy who would be interested in a bi MMF threesome. According to Kim she had over a hundred replys and it took her nearly a month to narrow down to one select gentleman. Steve was 32 years old, owned his own home and an accountant that worked for one of the large accounting firms in downtown Houston.

We met at Steve’s home one evening and I was pleasantly surprised to find that he was a very nice looking guy standing about 5’ 10”, weighing around 170 lbs, clean shaven, and with a full head of hair. After sitting in the living room over a few drinks for about an hour talking about our sexual histories Kim suggested that we take our drinks to the bedroom.

At this point I really wasn’t too nervous since I thought that Kim would be 90% of our focus. Boy, was I wrong. While Kim started the action by making out with Steve, he suddenly turned to me and gave me the warmest and most sensual French kiss I had ever experienced. Glancing at Kim I saw the biggest smiles I had ever seen from her as she also gave me the wink of approval. Steve and I stood there making out for nearly three or four minutes when he then suggested that the three of us strip down and get into his king size bed. As we underdressed I as amazed at his smooth body and rather large 8” cock.

Steve asked me to lay in the middle so he and Kim could properly focus on me. I certainly wasn’t going to complain and smiled as they both snuggled up to me. First, Kim leaned over and told me she simply wanted to watch me explore with Steve and how wet this was making her. As I slide my hand between her thighs I knew she wasn’t exacterating.

Suddenly, I felt Steve’s hand softly stroking my cock as he leaned over to give me another kiss that was even hotter and more passionate than the first. I surprisingly found myself feeling almost feminine as I placed both arms around his neck and started to caress the back of his neck and his hair like Kim so enjoyed doing to me. Quite frankly I had never felt so sensual in my entire life.

He then broke from my embrace and started slowly kissing my neck,then chest and working his way down to my very erect 7” cock. When he took my cock in his mouth it felt so different. Maybe it was the large size of his mouth, but all I know is that it felt wonderful.

As he slowing began to give me an unbelievably gently blow job, Kim leaned over and gave me a sweet but passionate kiss. While I wasn’t timing this, I am sure that I blew one of the biggest loads in my life within two minutes and Steve swallowed every bit of it and then came back up to give me another passionate kiss. I know that it was silly but I felt like I wanted him to truly be my boyfriend.

Next, he turned his attention to Kim, but she politely asked him to let me return the favor to him. I actually became nervous about going down on Steve and Kim immediately sensed it. She then suggest that we both go down on him. She started first as I gently caressed his balls and then she simply slid his cock to my lips and I intuitively began to take him into my mouth. I couldn’t believe how smooth and soft it felt as I slowly worked up and down on his beautiful shaft. I was honestly couldn't get enough and felt so rewarded everytime Steve moan. Then suddenly I could begin to feel him swelling up and then releasing, no exploding, into my mouth. I simply couldn’t swallow fast enough as it dribbled down my chin.

I think what surprised me most was that I wanted to keep going down on him when his cock became soft. Then Kim asked if she could join the fun. Needless to say over the next two hours the three of us had the most unbeliveable sex.

Before leaving Steve’s home that night Kim asked if I wanted to see Steve again except on my own. Steve gave me approving nod and I said most definitely said yes if it was alright with her. Steve and I then agreed to meet the following night at the same time.

Riding back to Kim’s house I couldn’t keep talking about wonderful Steve had been and how surprised I was at how feminine I felt. She lovingly laughed and shared that now I was beginning to know how wonderful it felt to be a woman. But what came out of her mouth next really surprised me. She asked if me if I wanted to dress up as a woman and be with Steve.

As you might imagine I wasn’t sure how to answer, but Kim began to tell me how cute I would be dressed up and that she would help me. Plus she added that she would think it would be hot to make love to me when dressed as a woman. After about 30 seconds of mental debate I decided to go for it.

Kim then called Steve and asked him if he would be interested in me coming back dressed as a woman and he enthusiastically said he would love it.

The next morning Kim asked me to completely shave my body, which took longer than I thought. I also put more lotion on my body then I thought would be possible. Then she and I began our shopping journey and along the way decided that my girl name should be Carly. By the way, my real name is Charlie so I thought why not.

At the time, I was making some pretty good money so Kim insisted that we buy some quality and stylish clothes one of the nicer department stores. As we did our shopping she was completely told the sales clerks that she was going to dress me up as a woman since it was a fantasy of hers. It was surprising how many winks we both got from the clerks!! We started with lace panties, a bra and pantyhose, then found a really cute short dress Just trying on the dress in the dressing room was such a huge thrill.

Next we started with makeup. I learned a lot that day about makeup and skin tone matching! Then we found a high quality wig store that specializes in wigs for women. Trying to find just the right wig seemed to be a joy for both Kim and the sales girl. In the meantime, for the first time I felt a little embarrassed.

The next stop was at an independent lingerie store to buy some falsies for women who had mastectomies. The hardest part of the shopping was finding shoes that would fit. The only place we could find was a Payless store. $3400 later (the full lace wig being the most expensive) we headed back to her house.

I followed Kim’s instructions to the T. A long bubble bath, shaving my entire body again, putting on tons of skin lotion, and then the makeup job began, which probably lasted over two hours because she kept experimenting and trying to teach me how to apply it. Finally, when finished, I had a hard time believing it was me. Next I got dressed and then the wig came on. Since it was a lace wig it took some time to trim the lace just right and to glue it on. When ready she stood me in front of her full length mirror and I was amazed at how sexy and beautiful I looked. This was such a high that there is no way I can begin to describe it.

As I twirled in my short dress and admired my gorgeous legs I knew that I could pickup most any man I wanted.

I have to admit that driving with high heels on took a bit of getting used to, fut it felt so sexy having my dress ride up my hose covered legs. When I arrived at Steve’s house he was obviously approving Carly’s look and immediately took me into his arms for a sensual and deep French kiss. Feeling his tongue explore the inside of my mouth felt so feminine and I wanted him to know how much of a woman I felt like. I loved telling him how handsome he looked and how much I wanted him. But Steve knew that he wanted to stretch the evening out. As we sat on his couch sipping wine, he would sweetly caress my legs, and lovingly look into my eyes telling me how beautiful I looked. Over the next two hours we listened to romantic music and made out like teenagers. He would let me stroke his cock through his slacks but would never touch mine. He would only slowly slide his hand up my dress and rub my scrotum.

Finally, when neither of us could stand it any longer we went to his bedroom where he slowly unzipped my dress and let it fall to the floor as we continued to make out. He next laid me on the bed and slowly removed my pantyhose while admiring my baby blue lace panties and bra. When we laid down he embraced me like the woman I felt like and I thoroughly enjoyed his passionate French kisses as he caressed my silky smooth body.

I so wanted to go down on him but he told me not yet, that he wanted to take his time and enjoy the feminine Carly I had become. After nearly 30 minutes of sensual making out and feeling out bodies so closely together that his stroking of my scrotum moved up to my gurl clit. When he slowly removed my panties he began to gently play with my new clit with his tongue, kissing it and occasionally taking it fully into his mouth and then licking and kissing it again. It was clear that Steve was in no hurry and nor was I as I was blissfully in an feminine zone that felt so wonderful.

I will leave the rest of the evening to your imagination. However, I will tell you that I have many, many times gone out dressed and picked up men. But none were ever as sensual and passionate as Steve. For that I will always be grateful.

Carly