David to Dee Dee

by Davey Fahrner

 

I was 18 at the time and out on my own for the first time in my life. I had an apartment, not too big, but good enough for me. I need a haircut and decided to go to the place down the block from my apartment. The sign said it was a unisex salon but when I went in, I was the only male in the place. The owner, Judy came up to me and asked what I wanted and I explained I'd like to have my hair styled. She smiled at me saying "I'd be happy to do your hair, how about waiting in the chairs and I'll be with you shortly."

As I sat in the chairs, there wasn't a single magazine for me, they were all fashion magazines for women. I picked up one and started to look through it. I was looking at the page of lot's of women's hair styles when Judy came over, looked over my shoulder and pointed to one in particular saying "this one would suit you very well. It's nice and soft, would frame your face beautifully. And very versatile style, you can leave it just out of the shower or use some curlers to give it nice body."

She then ran her hands over my hair saying "oh David, you have such beautiful hair. I know women who would kill to have so much hair. It's so full and the color, very pretty. I just love it. Let's give you that style, you'll look wonderful with it." I said I wasn't so sure and didn't she think it was too feminine for me. She smiled saying "well yes, it's feminine, but you can't think that way. You've got to think what style would make you look your best and I know it's this one. You just relax and let me take care of you."

With that, she took my hand over to the shampoo area. She put a cover over the shirt I had one and I felt really embarrassed. It was light pink, with small satin bows all over it, lace edging and little tiny embossed flowers. She simply said "we really don't have anything for men, I simply don't get that many men in here. In fact, you're my only male client. I'm so thrilled you've decided to let me style your hair, you're going to love it."

She proceeded to shampoo and condition my hair and then we went over to her chair where for the next half hour she cut it. After she cut it, she placed some liquid in it and then began to use a curling iron saying "this will give your hair even more body and if you want, you could use some curlers to give yourself some really tight, cute curls. But I won't do that, at least not today."

When I was done, she turned me to the mirror saying "well, what do you think?" I was somewhat stunned. I can't really describe it except to say that while it wasn't a totally girl style, it did give me a softer look as the hair was feathered, framing my face and she had even given me some bangs. I finally kind of smiled saying "looks great Judy."

She then made me fill out a customer card, giving her my address and phone number. Judy said she would call me in about 4 weeks for a trim. She handed me a round brush saying "after you shower and shampoo, use this brush to curl your hair around it so you keep all that fabulous body. And if you want, use the brush, curl it really tight and then use a blow dryer to give yourself some really cute tight curls, if you want, of course."

I used the brush each day as she said, although I never tried to give myself the tight curls she talked about. I went back to her salon every 4 weeks for a trim as well as more lessons in how to use the brush to give myself curls, which she had me do in the shop so she could watch me. I got to where I could do the tight little curls she wanted.

In addition, she had one of her ladies that worked for her give me a manicure every time I came to the shop. She had me grow my nails out just a little and she used a clear polish each time. Judy was quite pleased saying "your hands are almost as nice as your hair."

We were becoming really good friends and so she asked me one day if I would come over to her house and take care of some stuff and fix things. I had nothing going and so I spent Saturday afternoon doing little odds and ends for her. It was a really hot day and by the end of the day, I had become rather dirty. Judy had said after I finished that we would have some drinks and dinner.

She looked at me saying "oh David, you're so hot and dirty, would you like to take a shower?" I said yes and she said "while you're showering, give me your clothes I throw them in the washing machine." I asked her what I would wear and she said "don't worry sweetie, I'll find something for you." And so I went into her bedroom, took off all my clothes, leaving them on the chair she had pointed to and took a long hot shower.

Judy had left a curling brush and hair dryer in her bathroom saying "do those really tight curls for me." And so I did as she asked. When I had finished my hair, I went into the room with a towel wrapped around my waist, looking for the clothes she had left me. Well on the chair where I had left my clothes was a dress and panties. I didn't see anything else so I went to find Judy, who was in the kitchen and I said I didn't' see any clothes but a dress and panties.

She smiled saying "I know, that's what I found for you to wear." I could feel my face get a little red asking her if maybe she had some guys clothes. She laughed saying "David, I'm a single woman, living by myself, why would I have guys clothes." That made sense but then I asked her if maybe she had some pants I could wear. She said "I thought about that, but they won't fit you. Besides, I think you're going to look really cute in a dress. Now, go put it on and get back here."

I didn't know what to say so I went back to her bedroom and looked at the dress and panties on the chair. The panties we're pink satin with lace leg openings and a lace waistband with little pink satin bows. The dress was also pink, with lace trimmed neckline and was pleated from the waist down.

I stood staring at the clothes, kind of in a trance when I heard Judy said "David, come on, get out here now." It got me started and I dropped the towel quickly, picked up the panties and put them on. As I pulled them up my legs, I had a raging hard on, harder than I had ever felt and as the satin covered my cock, my body shuddered in excitement.

I slipped the dress over my head, letting it fall around me. I took a look at myself in the mirror, not believing how I looked. I had done my hair in tight curls, giving me a very feminine look and then with the dress, I look almost like a girl. I took a deep breath and walked into the living room.

Judy was waiting and smiled seeing me saying "oh David, you look so cute. That dress looks wonderful on you." I walked over to her and she had me turn around so she could see the dress from the back. She then said "pick up your dress, I want to make sure your panties fit." I told her I didn't think that was necessary, that they fit but she insisted saying "how would you know, you're a boy. Now, pick up the dress so I can see."

For some reason, I had to do whatever she said and so I lifted the hem of the dress up to my waist, knowing my cock was still rock hard. She had me turn completely around and when I was facing her again, she smiled saying "the panties fit perfect. Just so you know, you wear a size 6 in panties and a size 9 dress."

We had a really nice dinner and then sat in the living room talking after dinner. Judy was sitting very close to me, running her hand up and down my inner leg, keeping very hard and very excited. She knew the effect she was having on me as my breathing was becoming more labored. I was too excited and timid to stop her or say anything.

Her hand couldn't have been an inch from the leg openings in the panties I had on when she said, "I've always wanted a boy who'd let me make him pretty and dress him up in pretty, feminine clothes. And the best part of this David is you like it and you're excited by it, aren't you sweetie?" By now I could only moan a yes.

She then said "If you'd like, you can spend the night tonight, in my bed with me and we could have some fun. Of course, you'll have to wear something real pretty to bed for me. Do you think you'd like that David?" She had moved her hand right on top of my rock hard cock inside the panties as she asked and I again simply moaned yes. She then said "and you'll let me play dress up with you again tomorrow, make you a real pretty girl, take you shopping for some dresses, skirts, and some really feminine lingerie. You'll do that with me, won't you David?" Again I moaned yes.

She got up, pulling me up and took me into her bedroom. She opened her dresser drawer, removing a sheer, pink chiffon baby doll nightie with matching sheer pink panties saying "take off your dress and panties, put these on and come back to the living room." Being incapable of denying her anything, I did as she said, looking at myself in the mirror again before going to the living room.

The baby doll top stop at the waistband of the panties, and the panties being completely sheer, left my rock hard cock completely exposed. I returned to the living room to a completely naked Judy lying on the sofa, her legs spread wide, with one hand playing with her pussy and the other hand pinching her nipple. She smiled saying "you look darling David. And now, I need my pretty little girl to take care of me."

I come over, knelt before her and she pulled my mouth to her pussy saying, "Now, girls take their time, lick softly and gently." And so I began to lick her pussy. In no time at all she was saying "oh David, you're more girl that you can possibly imagine. Yes sweetie, just like that, keep licking baby."

I kept on licking for quite sometime and I know that she came 3 different times but even after coming, she kept having me lick her pussy. Finally she pushed my face away, smiled saying "you're such a good little girl, time for Miss Judy to take care of you. Stand up sweetie." I stood up and then she reached forward and pulled my panties down, my cock springing straight up.

She took my cock, began stroking it and then had me lay down on the sofa. She moved me around so my legs were going up the back of the sofa and my head was on my seat cushion. I wasn't sure what was going on until she started to push my legs back towards my head.

Well, I happen to be very flexible and the result of her doing this was my now fully erect cock was pointing straight down at my face, about 10 inches away. She took hold of my cock, began to slowly jerk it and asked, "do you know what's going to happen?" I thought I did, but I said no.

She laughed saying "well I'm going to keep playing with this very hard dick until it can't take it any longer and start shooting it's come. And when it does, my little girl is going to open her mouth and catch every last drop that comes out of this dick and she's going to swallow it. You have tasted boy come before, haven't you sweetie?" I said no.

"Well how exciting is this, you're first time wearing pretty feminine lingerie and now you're first time tasting boy come. You're really becoming quite the girl" She started stroking faster now and I knew it would be impossible not to come. I really tried to hold off and she knew it and said "that's right baby, hold back, try really hard not to come. Because doing that will cause that dick to shoot even more come. And when it starts to come, keep your mouth and eyes open. I want you to see it shooting in your pretty mouth."

I'm not sure how much longer it was but the pressure became too much. I watched as the head of my cock swelled twice its size and then it opened, at first shooting just a little come. It seemed like everything was in slow motion as my cock began spewing huge amounts of come into my open mouth. Over and over again it shot right into my mouth. All the while it did, Judy was saying "that's my girl, keep taking all the boy come, let that dick fill your mouth up before you swallow."

When my cock stopped shooting, Judy said, "before you swallow, swirl your tongue around, get a good taste of that boy come." I did as she said and then I swallowed down, in 2 large gulps. When I was done, she smiled saying "that's my girl. Now, let's put your panties back on and go to bed."

As we lay in bed, she had me snuggle up to her and she put her nipple in my mouth saying "from now on, when we play dress up, you'll be Dee Dee. Tomorrow, Dee Dee and I are going shopping for some real pretty clothes."

 

End Chapter 1

  

  

  

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