Afternoon Delight Turns into More

How an Afternoon Delight Became Much More

I was born into a large trust fund and had the good fortune of never having to work a day in my life. I would always have as much money as I needed and could do whatever I wanted. As it always is in life, when something good happens there is always something on the other side of things that happens to level things out. For me it was the size of my penis. I was born with a very tiny penis and ball sack that was really not a "sack", but was more of a small "mound" under my cock between my legs.

My tiny genitals had always been a point of embarrassment for me. In college, when other guys were talking about all the females they fucked, I never had a story to tell. I never had a girlfriend, and I had never had a sexual experience with another person in my life. I was extremely introverted and had no real friends. I lived alone and I liked it.

After college graduation at age 22 I began to become interested in wearing female lingerie. I had always admired it and it was of interest to me to try it on since my cock was so tiny. I purchased several different size panties in several different styles. I learned that my panty size was 8 and that I liked the full size nylon and lace style. I really loved rumba panties with the rows of lace across the butt. I began wearing pretty panties every day under my male clothes.

I was living on my own and I destroyed all of my male underwear so there would never be the opportunity to go back to wearing them. Wearing lingerie was exciting and I did not want that excitement to stop. I owned two dozen pairs of panties in all colors but I found I liked the pink ones and the white ones best with black being my third color of choice.

I delighted in being in public wearing my panties and knowing people had no idea what I was doing. It was about 90 days into this that I decided to buy several nylon and lace training bras. I found a size that fit and I purchased a couple of dozen in my three favorite colors. I began wearing my bra with my panties every day under my male clothing and it was impossible for anyone to know I was doing this.

As you can imagine, it wasn't long before I began to push further and further into being a girl. I had no normal penis or balls. I was very comfortable wearing a bra and panties every day. Why not see how far I could go with the ultimate goal of presenting myself in public as a girl? I would not be missed as a male as I was mostly a loner. I was thrilled at the possibilities.

I did lots of research on-line to learn what I could do to live my life as a girl. It was very easy to buy what I needed and even easier to get advice on how to live. I purchased several shoulder length wigs. A complete set of make-up, false eyelashes, lipstick, and finger nail polish. I went online to find a makeup artist who would teach me how to perfect my look and I found a lady who was more than eager to teach me. I also began shaving my entire body clean of all body hair. Legs, underarms, and chest hair were all removed. I had very little chest hair to begin with and after the first shave it never grew back. After two shaves my underarm hair never grew back. And after three shaves the hair on my lower legs never returned. My pubic hair was the most stubborn and to this day it requires a weekly shaving to stay completely away.

During my first makeup session the lady I hired explained how to do everything to get the look I wanted. I told her I wanted a "Girl Next-door" look and she knew just what to do. When my wig was pulled into place my instructor had a brief gasp of air before she said:

"My God, you are absolutely beautiful! I can't believe you aren't female."

When she had me step in front of the full length mirror I was wearing a half slip and camisole over my bra and panties and I too remarked:

"You're right. I'm shocked! I am the most natural female I have ever seen."

"You will have NO problem passing in public" she said. "If I were you, I'd think about staying dressed as a girl full time."

"There is really nothing stopping me from doing that" I replied.

"Then DO it!" She said. "You will have no trouble finding a man if that's what you want."

I thought about what she said and thanked her and paid her for what she had done and told her I would consider her advice. I had a closet full of dresses and shoes so I took off my panties and pulled on a pair of thigh high stockings and attached them to a satin and lace garter belt then pulled my panties back on and lowered my half-slip and then I followed this up with taking off my camisole and training bra and attaching a pair of silicone breast forms to my chest with surgical glue. I then put on a very pretty satin and lace bra to hold my new 40C chest and everything fit perfectly and felt wonderful and oh so natural.

I put my camisole back on and selected a dress that had an ample amount of lace on it and finished things off with a pair of flat shoes so as to keep my 5 foot 11 frame as small as possible. In the process I also painted my fingernails and toenails a lovely color of dusty rose. The finished look was unbelievable! I looked every inch a girl, and what I didn't know at the time, but it was more important, I began to mentally see myself as a girl and act as a girl. Being a female was very natural for me and I loved the way it made me feel.

I lived my life as a female for the next five years in total bliss. I was never second guessed in public. I subscribed to lessons to raise the level of my voice. I went to sleep every night listening to feminization tapes. I always slept in a nylon and lace nightgown with a pair of full cut panties on underneath.

Sexually I began to identify myself as a girl. My nipples were my most sexually sensitive parts of my body. I began to watch porn. I always chose male/female porn and found myself staring at the men's huge erect cocks and being fascinated at how the women reacted to having intercourse. I loved the way their eyes looked while they were being fucked and I studied how they guided the man's cock into their vagina. I found myself wanting more than anything to be one of those women.

I was very aware at age 27 I had never ejaculated as a male. I didn't even know if I could do it. I thought my body was not physically capable of ejaculating. This didn't really bother me as I saw my lack of cumming as a further sign I was truly a female. What kind of girl squirts sperm out of her body?

It was another year before I had a most unusual experience that caught me by total surprise. I had had my share of wet dreams over the years, but I had never been able to put together and orgasm with an erection. My "erections" when I had them, which was very rarely, only caused my little penis to grow to 2 inches in length. I had never once experienced an erection and ejaculation. My wet dreams were always with a tiny flaccid penis. I was fairly certain my body could not ejaculate like a male. Again, more evidence I was naturally a female.

Then one Sunday afternoon I was sitting on the sofa reading a magazine fully dressed as usual, when I was quickly hit with what I thought was an instant need to pee. I had been exclusively sitting down to pee for over five years at this time and the urge to go was so strong I knew I would not make it to the bathroom in time to pull up my dress and pull down my panties. I really didn't know what to do or what was going on it was all happening so fast.

I sat very still and resigned myself to the fact I was going to pee my panties. Instead my tiny flaccid cock began to release a continuous stream of what felt like warm, wet, sticky cream. It was not pee at all and I could not stop it from releasing. My pelvis began to jerk and twitch and every time it did I felt more cream flow into my panties. I gasped for air in little breaths and every time I did my pelvis twitched and released more cream. I found myself not wanting this feeling to stop. I did not care how much cream was piling up inside my panties. It was firm enough that it was not running down my legs, and I could feel it piling up over my limp little dick.

What I didn't know was happening was after 27 years of never once ejaculating, my body was finally doing what it should do. When the twitching stopped I lifted my dress and slip and pulled open the top of my panties and looked between my legs at a massive gob of white colored cream. I slowly slid my hand into the gob and it felt very warm and very sticky. So sticky I could not get it off my fingers. I found myself totally repulsed at the feeling and that I had no control over what I had done in my pretty lingerie. I felt very dirty and not in the least bit feminine. I stripped naked and got in the shower to fully cleanse myself of what I thought was the most disgusting thing that had ever happened to me. Little did I know that just two short years later I would be begging a real man to not only let me feel his cream, but to let me taste it and swallow it!

It was close to my 30th birthday when I got the courage to post my profile on a crossdresser dating website. Of course they wanted pictures of me and I had hired a female photographer to take several hundred for me. I told her what I wanted them for and how I wanted to present myself on the website. She knew exactly how to pose me and we took a few hundred of them with me fully dressed in my prettiest dresses and skirts and blouses. She then suggested I pose in my pretty lingerie which I gladly did. This was followed by pictures of me in nightgowns and baby dolls. And finally she suggested that I pose totally nude with clear shots of my tiny penis and ball mound. I was a little nervous at first being naked, but after a few shots I was very comfortable posing with my legs spread wide apart. My shoulder length wig and full makeup was in place and my little cock looked more like an oversized clit.

My femininity was clearly visible in every shot. I basically have no male physical features except my tiny, disgusting penis. My naked breasts are almost an A cup and I was in no way overweight. Slopped shoulders, not square. Wide hips, not straight. No visible Adams Apple at all. Zero body hair anywhere on my body. I am a girl with an oversized clitoris. And I was all of this without taking ANY hormones of any kind.

I posted 100 pictures on the website with just a couple of them showing me completely nude. I wrote a very clear description of myself and my current situation. I was clear that I was looking to begin a dating relationship with a biological male with the possibility of the relationship becoming long term, and, with any luck, I was open to the possibility of one day getting married and becoming a full time wife. I also made it clear that I was naïve when it came to the physical act of sex. But with the right man I was eager to learn all I could to please him in just about any way he wanted. When I looked at the others on the website I was clearly the most feminine girl with a tiny cock of anyone.

You can guess what happened next. In the first week I had 35 men answer my post, all telling me how pretty I was and wanting to meet me for drinks and possibly more. I was excited at the strong response. Anyone who didn't send a picture I rejected immediately. Close to 30 men sent me their picture and of those I selected five to begin a correspondence with. All five of these men looked very handsome and also sent a very sincere message that was also romantic.

I was very nervous but began sending emails to my potential dates. One of the five stood out among the rest in how loving and sincere he seemed to be. He told me he was not married which was a plus as the other four had wives. He wanted our first date to be at a very nice hotel bar where he said he knew the owner. I decided to trust him and agree to a date.

I spent most of the afternoon of the date getting ready and selected my prettiest lingerie and a dress I just loved that was covered in lace. My makeup was perfect and I looked even better than my best picture on the website. I drove to the hotel and walked into the bar and he immediately came up to me and introduced himself as Jack and told me how beautiful he thought I was. I thanked him and told him I found him very attractive and everything his picture showed, he was.

Jack was a very handsome man. Everything about him was masculine. Square shoulders, a thin waist, strong arms and legs with a light moustache that made him look amazing. I was smitten. I hoped the rest of the evening would go as wonderfully as the first five minutes did. I told him I was nervous and he put me totally at ease as he escorted me to a waiting table that had a bottle of champagne and two glasses on a white tablecloth. He pulled out the chair and seated me like a perfect gentlemen. The female in me was hitting on all cylinders. My tiny penis and ball mound pulled so far into my body I could tell the front of my panties were completely flat.

As we toasted each other Jack said to me:

"You are more beautiful than I imagined. I have never been with someone who is as feminine as you."

I knew from our emails that he had experienced sexual relations with five other girls like me before. He told me they turned him off by looking too much like males in a wig.

"But you Tammy, are totally different. You are so female. Are you sure you're not fooling me?"

I smiled and assured him I was not putting him on.

"I'm most comfortable as a girl and as you have noticed I am more female than several other ladies in the bar."

"You most certainly are." He said as he filled my champagne glass again.

We spent the better part of an hour at the table drinking champagne and getting to know one another and then the moment I knew would come arrived as he asked me if I would consider joining him in his room. I tried to hide my excitement as a good girl would but I'm sure I was not doing a good job of it.

"You have a room here in the hotel?" I asked.

"Well yes. I am good friends with the owner and he lets me have a room whenever I want one. I always have a large suite. We can continue in the living room."

The champagne was doing its thing when I told him I would very much enjoy seeing his suite.

"Wonderful. I'll have more champagne sent up and we can continue on my sofa."

The suite was beautiful. A full living room and bar area and through double glass doors there was a romantically lit king sized bed. I was a little nervous, but Jack was so gracious and accommodating I felt an instant attraction to him. We both sat side by side on the sofa.

"You are aware I have never had any kind of sexual relations with anyone before" I blurted out.

"You told me. I'm surprised that you haven't had several men wanting to be with you before now." He said.

"I have just never put myself in that position before" I answered.

"It took me a few years to realize I was a girl and a few more to learn how to live as a girl full time." I continued.

"How long have you been living as a female?" Jack asked.

"Over five years as of today, and I just love it." I said.

"if it will make you feel any more relaxed, don't feel as if you have to have sexual relations with me tonight. I would however very much like to kiss you if you don't object." Jack said.

I think he could see me relax as I said;

"I would very much like to kiss you. I find you very kind and very attractive."

With that he leaned over to me as I closed my eyes and our lips came together. Immediately his tongue thrust into my mouth and I welcomed it with love pats from my tongue. We continued to tongue kiss for several minutes as I put my hands on his shoulder. When I did that I quickly felt his hand sliding up my nylon covered leg and under my dress. I was still totally flaccid and pulled inside my body when his hand reached my panties. He pulled his mouth back from mine and said:

"You are right. You are a girl. I can't feel any kind of a penis in your panties!"

"It's the way I like it and the way I live." I said.

"Tammy honey, I am really attracted to you! You are a beautiful girl." Said Jack.

"If I'm moving too fast let me know" he continued.

I decided to be honest and said;

"It's a little fast for me. Would you object tonight if all we did was kiss and caress each other while we kept our clothes on?"

"Of course!" He replied. "Anything you want. I want to please you any way I can and I have a good feeling this will not be our last date."

"I have that feeling too, and I'm sure it won't be." I replied.

"If I can ask one thing, I would really love to see under your dress and to see the front of your panties. I'm fascinated to see how feminine you look." Jack asked.

"Because I have a good feeling about us I will be happy to show you my panties. I would like to stroke the front of your pants to feel if I am making you hard." I replied.

"Honey, I was rock hard from the first moment I saw you walk into the bar, but of course you can stroke between my legs."

I stood up and slowly lifted my dress and slip to reveal my nylon and lace full cut panties with a perfectly flat front to them.

"You're gorgeous!" said Jack. "And you are without a doubt a girl."

As I lowered my dress I put my hand between Jack's legs and felt an enormous penis that was thicker than anything I imagined.

"Oh my! You are a big boy!" I exclaimed.

"I can't help it when I am with you." Said Jack.

"But let's just kiss and call this a night. I would love to do more, but I want you to really be into the moment and I don't want you to be nervous." He continued.

"Thank you Jack, you are a real gentleman. I have no doubt I want to do more, but would like to take some time to think about what has happened tonight."

"Not a problem" Said Jack.

"Would it be too forward of me to ask if you and I could get together again the day after tomorrow?" I asked.

"The day after tomorrow would be perfect," said Jack.

We kissed and hugged a final time for another five minutes and then Jack escorted me to the door and I drove home feeling woozy and anxious for the day after tomorrow to arrive.

Our next date started in Jack's hotel suite. After a couple of drinks I was the one who began to unbuckle Jack's belt and unzip his pants. His boxers could barely contain his huge erection and I immediately pulled them down to reveal a thick eight inch long cock with a wet glistening tip.

"Oh Tammy, I would love it if you would take my cock into your mouth and I will tell you where to lick me as I feel I am very close to cumming." Said Jack.

I did as Jack asked without hesitation. I could not take his whole penis into my mouth but he told me to lick the shaft and flick my tongue around the hood of his cock. As I did this I felt his cock swell even larger and in an instant shoot hot cum into my mouth. Instead of being repulsed I shoved as much of his cock into my mouth as I could and began sucking his monster stick of every last drop of semen he had. The taste of his cum was wonderful. I felt his cock starting to get soft as I pulled my lips back and with a mouthful of cum said:

"I love you Jack."

It's all I could say before I began swallowing his warm sticky cream which I swirled around my tongue on it way down. Jack fell back on the bed and said;

"Is anything happening between your legs?"

"Nothing at all" I replied.

And in fact if it was possible my little penis and ball mound was pulled back inside my body farther than it had ever been before. But my nipples were fully engorged and as big as pencil erasers.

"I would love you to suck and kiss my nipples right now" I managed to say.

Without any hesitation at all, Jack pulled off my dress, dropped the straps from my slip and unhooked my bra. My nipples were huge and were a color of red I had never seen before. Jack pushed me gently back on the bed and climbed on top of me and began licking and sucking my nipples until I was in a sexual frenzy.