Crystal's StorySite


Thanks to Carol

Debra Lynn Messer


It all seemed simple enough. I had been dating a wild and kinky girl. She wanted to have a little fun one night so I figured I would go along. I had no idea how far it would take me.

Carol is the type every guy wants to find. She is sexy, long blonde hair and green eyes. She has a body to die for. She is 5'6", 36D-24-36. She is also totally into sex. So one night she wanted to tie me up. I figured that there was no harm in that and kinda liked the idea. It was cool, but later she decided to take it further.

I came home from work one day and found a large box with a note taped to the top. The note was from Carol and told me to apply a cream to my entire body then shower after a fifteen-minute wait. I did as she requested. The cream smelled terrible but I followed her directions. To my surprise I noticed my hair falling off as I showered. I got out and shaved again and inspected the "new" look I now had. It was strange not seeing all my body hair, but didn't really bother me.

When I came out of the bathroom I notice Carol sitting on the bed.

"Good", she began, "you did like I asked."

I had to admit I was a little concerned about it but figured if it involved sex with Carol it was going to be unforgettable. Little did I know just how much though. Carol opened the box and produced a lacy bikini panty.

"Turn around", she instructed.

I did and she had me bend over. With nearly expert precision she stuff my balls up in me and taped my dick up between my legs. I was almost afraid to know where she learned to do that, and decided to not ask.

"Now you can put on your panties", she said.

I put up a little protest, but Carol promised it would be the most unforgettable night of sex I had ever had. I though about how wild she could be in the sack and figured I had nothing to loose. I slipped on the panties and was told to lie down on the bed.

Next came two large breast forms. Carol attached them to my bare chest and held them for a moment so the adhesive would take. I noticed that they were very natural looking and moved gracefully as I got back up. Then came a matching bra. I couldn't help but notice how great these breasts looked on me. I had always wanted to see myself with tits like these but had never told anyone about my desire. Then Carol went to work on my face. When she was finished She gave me a pair of black seemed stockings. I rolled them on at her request and Carol checked the seams to make sure they were straight, a short leather skirt that snapped up the side, and a sheer white blouse. She then produced a long Auburn wig and placed in on my head. When she was done I was given a pair of black paten 5-inch heels that buckled around my ankle. I finally able to see the result of her work in the mirror.

It was stunning. There was no way I could believe just how different I looked. I looked like a real woman. Carol stood behind me admiring her work.

"Well", she began, "what name do you want? You surely can't look like sex on legs with a name like Brian."

After a few tries we agreed on Debbie. Carol then handed me a purse and told me to follow her. Carol and I went out to the car and got in.

"You are going to love this place", she said, "I found it a couple weeks ago".

I tired to remind her that I was a guy wearing woman's clothes. Carol pointed out that no one could tell and that we were going to a lesbian bar so I would be okay.

While we were there Carol kept correcting me. She told me how to sit and how to stand. How to sip my drink, eat and even to sound less "male". It was quite an evening. The next day she got me all dressed up again and took me shopping. I had to admit I nearly freaked out at the mall, but soon realized that the guys eyeing me had not made me but were more interested in making it with me. We went to several stores buying a lot of different things. I was getting so relaxed with myself I couldn't believe it.

"So how are you enjoying your first new day?" Carol asked. "Isn't it wonderful being so feminine? Just wait till tonight when you get the entire treatment?"

I told her that it wasn't nearly a scary as I thought. I tried to find out more about what she had planned, but she just smiled and said it would be special. Every time I tried to bring it up she would cut me off and make a comment that only made me want to know more.

We got home after 8:00 that night and Carol had me change into what I had worn the previous night and to lie on the bed. I did and she came in a tied me to the bed and propped up my head.

"Sweetie", she said, "it has been a weekend of firsts for you. Your first dress up, shopping and time out as Debbie. It isn't over yet either. You will get to experience yet more first tonight."

I could feel my dick strain on the tape just wanting to know what kind of sex game she and I were about to share. Then she went to the door and opened it. In came a guy. He was tall and built. His muscles were cut and well defined. Then I noticed his enormous cock. It was huge, easily 9 inches long and 4 around.

Carol smiled and led him to the bed. He sat on top of me and placed his cock on my lips. Grabbing my head he tried to push his pole in my mouth. I kept my lips tight and tried to get loose.

"Don't fight it", Carol said, "it will be so much easier if you just enjoy it."

Not thinking I opened my mouth to protest. No sooner did I have my lips parted then I felt the stiff cock ram its way into me. I gagged at the size of it in my mouth. Again I heard Carol telling me to relax. I tried to get loose but his huge hands held my face on him. He pushed in again trying to get the entire length in me. I gagged a few times but slowly gave into the mass of man-meat now in my mouth.

"Good Debbie", I heard, "just suck as he feeds you his cock. It is easy. Just relax and service his big cock. You will get his cum soon enough. You better not drip any either. Girls always suck down every drop."

What the hell was she saying, I am a guy and this was not my idea. I did notice though I was beginning to actually enjoy it. As he rocked his cock in and out I was able to get more in. It wasn't long till he had his entire shaft in my throat. I was moaning as he kept fucking my mouth. Then with a couple quick thrusts I felt his cock swell up and cum hit the back of my throat. Wave after wave of the thick salty cream came shooting out. I worked hard to not let any escape. Even after he finished I became aware I was still sucking his now softening cock. He pulled out kissed me on the head and got off the bed. He kissed Carol on the check and left.

Carol then came over and untied me and told me to roll over. After she retied my arms and legs again she let me know what she had planned.

"Debbie", she said, "that was wonderful. You did a marvelous job on your first cock sucking. I hope you do as well on your first fuck."

With that she opened the door. A second guy came in. He was just as big as the first. Carol unsnapped my skirt and cut the panties so she could pull them off. While she was doing that he was rubbing his enormous pole with lube until it glistened in the light. Carol applied lube to my love hole and worked in.

"Sweetie", she said smiling, "please try and relax this time. You will find it much nicer if you do."

With that he held his pole began to push it in. I cried in pain as he worked it deeper into me. No matter how much I begged he kept pushing his cock deeper into my back access. Finally the sharp pain gave way to a dull ach. I could feel his balls against my ass as he began to slowly pump his cock inside of me. With slow deliberate motion he pulled back, leaving only the swollen head in, then drove down again. Again and again he drilled my backdoor. I winced as he did, but began to notice the pain going away. As he kept fucking me I began to feel a warm tingle. I noticed that my sounds of pain were becoming squeals of pleasure as he continued to pump me from behind. Then I felt myself rocking my hips to meet his thrusting cock. I was moaning and grinding on his cock. Again with a few quick deep thrusts he rammed his pole deep in me and let loose his load. He kept his cock in me as it pulsed over and over filling me with the warm fluid. As he came I noticed I was too. My dick was pumping its cum onto the bed I couldn't help myself as he filled me. When he finally climbed off and left I could feel the oozing of cum on my thighs. Carol untied me and told me to clean up.

I wiped the dripping cum and cleaned up. Carol told me not to remove my bra or stockings when I came back. I got into bed with her and had the most incredible sex I had ever had. Carol made me cum three times that night before I just collapsed from it all.


The next morning I woke up and went to take a shower. Carol was already out of bed and I heard her in the other room. While I was in the shower Carol came in.

"So Debbie", she said, "you sure had a quick learn. Isn't it great being a real woman? I know you will be happy."

With that she left the room. Needless to say I was a little worried. I had no part in choosing what has happened last night. Granted, after the initial shock of it I did find it enjoyable. I finished my shower and dried my self off. I then went to get some under ware and that was when I began to get her point.

I opened the drawer to find it full of panties and bras. Carol was standing in the doorway smiling, as I looked them over.

"What is all this", I asked, and where are my clothes"?

"Those are your clothes silly", she said almost mockingly, "I figured no girl could wear the awful stuff you had so I destroyed them and got you these".

I was told that I could keep my male clothes, but would only wear panties, bras and stockings. When I got home I was to change into something much more feminine. After searching my clothes I noticed I had one suit, two slacks, two coats and about eight shirts. Everything else was women's clothes. Even my sneakers had been replaced.

Breakfast was a little different. Carol informed me that I was to eat a simple breakfast and add "vitamins" everyday. I didn't argue too much. I did enjoy the dressing and I figured as long as it was at home I could accept it.

When I got home that day Carol had me take her to her doctor. They talked and did their stuff and I was just lost in a magazine while it all went on. All of a sudden I noticed the doctor in front of me holding a needle.

"Ok", she said, "your turn".

I was taken back, probably because I was not listening. She said I had to have the shot. I looked at Carol and then the doctor. They were both just waiting so I let the doctor go ahead and give me the shot. I was told that I would have to return each week as part of the treatment. I agreed and we left.

About a month later I noticed that I was different. I had considerably less hair and my skin was soft and sensitive. I also noticed that I was beginning to develop breast tissue. I was concerned and wanted to know what was happening. Everyone kept me in the dark for several more weeks. Finally I had to get a job that allowed me to work from home because I now had definite C-cup breasts.

That was when things really started to change. Since I had quit my job I had begun to dress full-time. I had my hair styled and grew in out much longer. My nails were manicured and polished. I could hardly tell who I once was. As to sex, well it was a past dream. Not that I could get it up if I had the chance.

Then one night Carol had me get all dressed up for a night out. I choose a short black leather skirt and red satin blouse. I had a sheer black bra and thong. I was wearing 5-inch pumps that buckled around the ankle and sheer seamed stocking that had a lace band at the top so I didn't need a garter.

I was just finishing my make-up when the doorbell rang. Carol let in two really hot looking guys. She introduced them as Brad and Tony. Brad was her date and Tony was mine after the usual hellos and such we made our way out the door. Tony held the car door open as I, as gracefully as I could, got in. Carol and Brad went in his car. We all went to a very nice restaurant for dinner and dancing.

I was a little nervous about he whole thing. Carol and I went to the ladies room and she explained that it would all be just fine and not to worry. Carol left and went back to the table. I open my purse and was looking for my lipstick when I noticed that I had condoms and a small tube of lube. I dug around and found a note from Carol telling me I should always be ready. I touched up my lipstick and joined the rest of the group.

Dinner was wonderful. The food was perfect and Tony was a dream. We danced and had drinks. Finally Brad suggested we go. I saw him and Carol drive off towards our place and Tony took me to the local make-out spot. I knew what Carol was doing and it bothered me some. She was my girlfriend. Of course the last few months couldn't prove that. I was more female than male now. Here I was dressed to thrill and had my own set of breasts. I had been taking shots to not only increase my feminine side but to block the male testostone. The "vitamins" were also part of the plan. Now I was in a car with a hot guy. More importantly I wanted to be here. I wasn't like the last time when I was tied to the bed.

Tony leaned over to kiss me. I responded to his kiss. I felt myself move my hand to his thigh. I was beginning to stroke his swelling cock as we kissed passionately. Tony started to unbutton my blouse and unhook my bra. As he was fondling my breasts I undid his pants and helped him slip out of them. Without a second thought I went down on his cock. I began to suck his rod while he ran his fingers through my hair. The more he did the harder I sucked. Slurping as I bobbed my head in his lap. I could feel him tensing up, trying to keep from shooting his cum. I sucked faster as he did. Then he let loose with a vengeance. Unable to hold back, his cum shot into my mouth. Wave after wave of man juice pulsed from the head of his cock. I drank down every drop and sucked his cock until he was soft.

"That was incredible", he said as he tucked himself in, "you are better than Carol said."

When we went home Tony walked me to the door. He wrapped his arms around my waist and kissed me deeply, his tongue probing my mouth. As I opened the door I heard Carol crying in joy from her room. There was no doubt that she was getting a good fuck by the sound of it.

I took Tony's hand and led him into my room. Tony had explained that he knew about me and I decided since he did it was okay. Besides, with what I heard from Carol's room I figured I needed to do it to. Once in my room I stripped Tony down and went to work on his cock again. He was just about to shoot when he flipped me on the bed and took control. He slicked up his cock and slid it inside of me. It was wonderful. He began to rock his tool in and out of my ass. I was moaning and crying at the joy he was giving me. I shuddered with each trust of his cock. Then I felt his pole swell and shoot his cum deep into me. I cried out in joy as wave after wave of fluid filled me. It was glorious and we collapsed when he was done.

The next morning I saw Carol sitting in the kitchen. Tony had given me one last good fucking before he left. Carol had that fresh fucked look on her face too.

"So", she began, "tell me are you glad you are Debbie now?"

I was at a loss for words. Not that long ago I had fought this. Now I was here and about to compare notes about getting balled with my "girlfriend".

She smiled and said, "I knew you would want to become a woman. All I needed to do was get you started. I could tell that first night."

I stopped and asked, "What do you mean"?

Carol settled back and began. "That night I tied you up I could see that as it went on you enjoyed it. Later I got you a little looped and you admitted your secrete desire to be a woman."

I knew she was right. All my life I had wanted what I had now. Now I had the chance. My job allowed me to follow it. Carol had shown me that last night I was ready to do it. The next day I went to the doctor again. This time I made the decision.

Thing are different now. Carol and I date men regularly. We live as two girls. I now have DD-cup breasts and will soon have a pussy. All because Carol gave me the chance to become the woman I want to be.




2003 by Debra Lynn Messer. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.