How I Learned to Date as a Girl

Learning how to date as a girl

By the time I was 25 years old I had really perfected my female look and practiced acting and thinking like a girl. I was very confident in my look and actions. I had been out in public many, many times dressed as a girl and I blended in perfectly. With this type of confidence I decided to take the next step and see if I could date a biological male as his girlfriend. I didn't want to trick anyone, so I decided to look for crossdresser dating websites. I have well over 500 pictures of me in all types of outfits and in various stages of dress and undress. I found a site I liked and I posted a profile along with about 50 of my pictures and in just a couple of days I had five different men who wanted to date me.

The very first time was the scariest. I asked each man to send me their picture prior to me accepting a date, which made the huge assumption they would be truthful. To my surprise, I never answered the door for a date and did not see the person I was expecting from their photo. I always met my date in a hotel suite with a living room, kitchen, and a bedroom and bathroom.

I would always arrive several hours early to get ready for the date and I would take a hot bath and do one final shave of any type of body hair so that my body was completely smooth over every square inch. I spent an hour or two putting on my make-up and doing my hair. Then I would put lightly scented talc on all of my body which made my lingerie slide on easily and the feel of the nylon and lace lingerie against my completely smooth body was a feeling that I just loved. I was perfectly put together when date time arrived and while I waited the first time I thought my heart would beat out of my chest. When there was finally a knock at the door and my date had arrived and he was just who he said he would be, I calmed right down.

Over the years I have dated six men in total. Five of the six we dated at least three times. My experience with real males who like to date a girl like me is they are all very well mannered. All of them complimented me on my look telling me I was very beautiful (which I just loved when they told me.) My complete female look and actions I believe brought out the best in the men and they went out of their way to be respectful of me and be gentle and loving at all times when we were together.

A first date usually started in the living room of the hotel suite with us sitting together on the sofa and talking, sharing champagne, and me sharing my photo albums with them of my large collection of photos. At my very first date, as the champagne eased both of our nerves, my date began by gently sliding his hand up and down the back of my blouse. He could feel my bra strap and like it that I was fully and cleanly dressed as I should be. As he looked into my eyes I could tell that we were making a slightly deeper connection and he very politely asked me if he could kiss me.

I responded "absolutely" and with that his lips touched mine and his tongue slid directly into my mouth without any resistance from me. Our tongues met and we immediately were sharing a truly intimate, passionate, kiss. I really enjoyed it, and from that very second going forward I knew I truly was content and happy to be a girl making love to a man. Everything about it felt right and nothing felt akward.

I stood up and took my date by the hand and asked if he wanted to continue in the bedroom. As any man would, he immediately said "yes!" As we sat on the edge of the bed and started kissing again I felt his hand move up my nylon stockings under my skirt and toward my garter belt. In response to this I slid my hand to the front of his pants and felt a very large and very thick penis between his legs growing larger right at that moment.

I have learned something from dating real men that I never knew before. A real man's erect penis is always very thick around in my experience. My tiny little cock is a pencil point compared to the men I have seen naked and who I have enjoyed lovemaking with. This was my first time feeling such a large thick penis and it was a bit startling, but more exciting than startling, and I began to imagine what it was going to look like.

I asked him he would take off all his clothes before helping me undress and he gladly agreed. He went into the bathroom and a couple of minutes later came back totally nude, with a large, thick, erect penis that stood out straight as a board in front of him. I couldn't take my eyes off his cock and marvel at how big it was. I quickly remembered he was this sexually turned on by kissing me and being with me and the power of my female look was something I REALLY enjoyed.

I was overjoyed at the fact my tiny deformed penis was not in any way shape or form hard in my panties. I was limp and tiny as always. My sexual excitement was coming from deep inside my body and I wanted to put my mouth on my date's cock as soon as I could. First, I stood up and he unbuttoned my blouse and removed it and then he slid my skirt to the floor. I was wearing a half slip and camisole with lots of nylon and lace.

I told my date I wanted to kiss his cock at that moment and he lay back on the bed with his huge dick pointing straight up. It was my first time ever putting a man's erection into my mouth, and I experimented with a few techniques to see what he liked most. First I kissed the head and then I inserted the entire hood into my mouth closing my lips around the rim. After that I took my tongue and licked around the base of his thick red penis head. That was what got him going. I ran my tongue up and down the length of his shaft and marveled at the thickness. By the time I got back to the tip I could see pre-cum starting to find its way out and I licked it up and found the taste very enjoyable.

He was breathing heavy and said "don't stop, you're doing great!"

I continued around the lip of his penis head with my tongue and in a minute or two I heard him say "I'm getting ready to cum and I have never experienced a cum like this before."

I responded by saying "let me catch as much of it as I can and I would really love to see you squirt a line from your cock."

His next sounds were a grunt and the words "I can't stop" and with that I watched a white rope of semen shoot out of the tip of his pulsing cock. I immediately put his penis in my mouth and felt at least 5 more streams squirt into my mouth. The taste and the feel of the experience was intoxicating. With a big load of semen in my mouth the most normal thing to do was swallow and swallow I did!

And the entire time the only thing hard on my body were my nipples. My tiny penis had actually pulled back inside my body which surprised me, I was completely immersed in the role of being a girl and it was totally natural for me!

As the two of us settled down on the bed, my date put his arms around me and hugged me and we cuddled together. We lay there in each other's arms and relaxed back as both our bodies returned to normal

He asked me if I had cum and I said "no."

Then he said "what can I do to help you cum? And, do you cum? You're such a pretty lady."

I told him I can cum if he wanted to lick and kiss my nipples.

He immediately helped me take off my bra and breast forms and began to lick my already hard round nipples. In just about five minutes I felt muscles deep inside my body start to contract. I told my date he was loving me perfectly and I was feeling like I was going to cum.

He asked me if he would see it and I told him he could if he lifted my half-slip and removed my panties.

He followed my instructions in one smooth move and then returned to licking and kissing my nipples. I began to gasp for air and told him I was ready to cum. Without a cock standing out of my body it was hard to tell, but when I screamed "I'm Cumming" my tiny penis head began flowing with white semen.

Not in violent squirts but in one constant stream of cum that just kept flowing. He was looking between my legs as I again said "I'm Cumming" and he saw my steady discharge and said "that is so cool! You are really Cumming like a girl."

I smiled and in about a minute or two the stream ended and my entire crotch area was covered with warm, wet, lotion. I put my hand between my legs and rubbed the white lotion all over my smooth and hairless crotch area. I had done it! I had made love to a real man as a woman. That first date gave me all the confidence I needed to try it again and again.

Over the years I have been with six different men. Five of the men were circumcised and one was not. For the one who was not circumcised, I really enjoyed watching the bright pink head slide itself out of his sheath and expose itself.

The stories that an uncircumcised man's cock is more sensitive are true. When I ran my tongue around the bottom of his cock head he squirted a white rope immediately. I ended up having at least ten dates with him and loved every one of them. The sixth man I dated has been a "keeper" for me as we are currently living together as a male/female couple. I'll let you know about our life together in Part 3.