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The Birth of Amber Lynn

A man plays dressup and realizes it has been the missing ingredient in his sex life
I had been dating Suzanne for about two months. She was a gorgeous woman I met while working as a computer technician at Aritech Computing. A successful sales consultant for the company, she made them a lot of money through all her sales. One look at Suzanne, and men would open their wallets to buy whatever new gadget or software she touted as being new and improved. As such, she in turn made a lot of money and no longer had to worry about making ends meet. She could have just about anything she wanted. She was quite a catch and I loved going out with her. Men everywhere went out of their way to talk to her and I marveled at just how easily she could work them into a frenzy.

Suzanne was somewhat of a sexual deviant. She loved dressing men up as woman. The first time she approached me with this proposition I had to laugh. Me play dress up? You've got to be kidding me! Even though I was tall and slim, I considered myself a tough guy from the streets of New York. She assured me it was all for fun and that she found it a huge turn on. One night while drinking too many rum and cokes, I foolishly agreed to let her make me up, but my only stipulation was that she couldn’t ever tell anyone. “Of course I won’t say anything, but you must do everything I want or the agreement is off,” she said.

“Yeah, okay, so what do you have in mind?” I asked.

Suzanne replied “This Thursday, we both don’t have to work, so come over at two o’clock and I’ll have everything ready for a nice and enjoyable evening. You’ll see, this will be fun for the both of us.”

All week I thought about our Thursday date. Why had I agreed to something as ridiculous as playing dress up with Suzanne? In hindsight, I realized she had dropped many hints as to enjoying girly men, crossdressing, and transvestism, but I never really gave it much thought. I loved having sex with Suzanne, but I have to admit, it wasn’t mind blowing. I had had better sex with other woman and I knew it was just a matter of time before I stopped dating her and started looking for another girlfriend.

Driving over to Suzanne’s apartment I felt a little apprehensive. I had never been dolled up and the closest I had ever gotten to experiencing femininity was when my first girlfriend put mascara on me. She said I had the longest eyelashes she had ever seen and wanted to see how they would look with a thick coat of mascara. She first curled them using an eyelash curler to open them up and then put on the mascara. I remember the feeling well because it was very sensual sitting there in her bedroom as she put makeup on me. She loved the way it looked and said she wished she had my girly eyelashes. That was a long time ago and nothing more ever came of it.

I parked out back and walked around to her front door. She was waiting anxiously for me and said “Come on in and go straight into the shower.” Shower? What? I was clean, why would I need to take a shower? Sensing my confusion, Suzanne said, “I want you to be ready for your transformation and any transformation to femininity starts with a blank canvas…wash up and I’ll be right there to help you with your shaving.”

“Shaving? Oh, I don’t think so Suzanne,” I said.

She replied “Remember our arrangement dear, you are to do everything I desire, you agreed.”

"Yeah, I remember, I was a little drunk and now I guess it’s showtime." Heck, the hair would grow back, no big deal, right?

I stepped into the bathroom, removed all my clothes, and jumped into the shower. Suzanne came in and handed me a wash cloth with a lot of Velvety Floral Body Wash. It smelled completely like a pretty woman and it felt odd washing up with woman’s body wash. She instructed me how to properly shave my legs so I wouldn’t get any unnecessary burn or irritation. Her pink double bladed shaver did a remarkable job of removing all the hair from my legs. She had me turn around and then she shaved the little hairs on my rear. That was also strange, but Suzanne insisted it was necessary. Then, Suzanne had me lift up my arms and she carefully shaved them bare. What the hell, might as well go all the way, I thought. She next ran the razor over what little chest hair I had. Toweling off I was truly amazed at how my skin felt, silky smooth, like a combination of satin and silk…it was so different, but was also wonderful at the same time. Looking in the mirror at my six foot tall and slim frame with no hair was very weird, but it did have a very feminine look to it.

Next, she handed me a tube of moisturizing cream and it too, had a very feminine smell. I rubbed it into my cleanly-shaven skin and it immediately felt exhilarating. Then Suzanne told me that she wanted me to tuck my penis and testicles up and that she was going to tape everything into place. This was going too far, but she assured me that there would be no permanent damage to my manhood and that it would be necessary to achieve that truly feminine look. I did as she instructed and then once everything was tucked away she handed me a black satin and lace-topped gaff, which ensured everything would remain in place. Looking sideways into the mirror I had no trace of any bulge across the front of my crotch. My body was starting to definitely take on a female appearance.

Then Suzanne grabbed a matching satin waist cincher and wrapped it around my waist. It had hook and eye closures in the front and laces in the back. She fastened the front and then spinning me around, pulled tightly on the strings to shave off a good four inches from my already narrow waistline. Now my figure was flat, firm, and slimmed in all the right places. It wasn’t too uncomfortable, but I wondered how I was going to bend down if I were to ever drop anything.

Next, Suzanne picked up the third item from this beautiful ensemble, a matching bra, which was the sexiest piece of lingerie I had ever seen. It had satin and lace throughout and the tinniest little black bow tied to the front between its 34B cups. The straps were also nicely trimmed with lace. She had me put it on by fastening the eye and hook in the back and then spinning it around my chest; she helped me with routing the straps through my arms and onto my shoulders. I noticed the cups were empty and she said, “No problem my girly girl, I have just the right thing for that."

With that she produced a matching set of false breasts made of silicone gel. She said they would heat up to my body temperature and would become a part of my new body. She carefully placed them in and adjusted the forms and bra straps to get the look just right.

I loved the way the breasts gently tugged on my bra straps and leaning over I felt their full weight and wondered just how woman with larger breasts must feel having them all the time. I had to suppress the feelings that I was doing something totally unacceptable and hoped that no one would ever find out about this tantalizing episode.

Then Suzanne had me sit on the edge of her bed and she rolled up a pair of nude lace top stockings. She attached them to the garters hanging from the waist cincher. It was such an odd feeling to be standing there in a woman’s bedroom wearing her sexy lingerie, but Suzanne said just to go with the flow and enjoy the feeling of being transformed into a woman. I have to admit, I was already sold and I loved this game. I felt alive and free, to experience what a woman experiences without guilt or shame. After all, Suzanne said I’d be doing her the greatest favor because she liked men dressed as woman. I didn’t think I could really look like a true woman, but wearing all these feminine articles made me start to feel like a woman.

Suzanne had pulled out several pairs of shoes and each one had no less than 4 inch heels. The first ones were your classic pumps with an ankle strap. The second pair was an open toed version of the basic pump, and the third was a platform heel with three studded straps that cut across the front and two on the ankle and all fastened with buckles on the outer sides. “Which one would you like my dear,” she said. I thought about all three, but deep inside, I wanted to achieve the image of a total tramp, so I asked to wear the strapped platform heels. “Good choice,” she replied.

Stepping into the heels was easy, but standing up in them and walking was hard. Suzanne needed to buckle them up because I couldn’t easily bend over due to my extremely cinched waist. I was definitely taller and felt sexy with my new feminine look. Suzanne then helped me over to her makeup table where she said she would begin the next phase in my transformation. I had never realized how extensive applying makeup could be, but now understood why woman never wanted you to show up early to pick them up. She spent a solid two hours on my face.

She started by prepping my face with concealer, foundation, powder, and then blush. The smell and feeling of makeup being applied to my face was very sensual. I really started to feel like a true woman. The tight lingerie around my waist, the gentle weight of my breasts and the feeling of the cool breeze from the open window on my silk-covered legs was nothing like I had ever felt before. It was very easy to forget that I was really a man. I decided to play the role up to the best of my abilities. I asked Suzanne how I was looking and she shushed me, “Not yet my pretty darling.”

She then moved onto my eyes and applied at least five different shades of eye shadow, followed by liquid eyeliner and a thick coat of mascara. Like my old girlfriend, Suzanne agreed I had long eyelashes, but insisted that a pair of falsies would enhance the slutty look she was trying to achieve. So, on went a pair of false eyelashes. The feeling of false eyelashes is by far the biggest turn on. Every time you blink, you’re reminded that you’re a beautiful and sexy woman.

Suzanne then spent a good while working my eyebrows with tweezers and a small brush. She said, “Don’t worry; I’m going to use concealer to sharpen your natural arch without taking too much hair away. I won’t do anything too drastic.” Then using an eyebrow pencil she colored them in and extended the tips to fully shape my brilliantly painted eyes.

After carefully lining my lips with a dark red lip liner, Suzanne applied a luscious coat of British Red lip stick. She then brushed in a top coat of clear lip gloss. She was apparently pleased because she said, “Yes, these lips will draw a lot of attention from all the boys and men at the club.”

Wait, what club was she referring to? I wasn’t going out dressed like this. She reassured me that it was only a general statement and not to worry, we wouldn’t be going to any club tonight. What a relief.

Then Suzanne had me slip into a black satin half-slip. She said it would make my skirt flow more easily across my hips. Next came a very short jet-black tight-fitting pencil skirt. It fit my new waist line like a glove and made my hips appear at least six inches larger than my waist, just as a sexy woman’s should look like. Before fastening the skirt all the way up, Suzanne had me put on a dark red satin button up blouse. It felt cool to my skin and gave me goose bumps. She tucked the shirt into my skirt and then fastened the skirt all the way up. Then she fastened a three-inch wide and sexy black patent leather belt with a gold buckle around my waist. I was totally feeling feminine. This was as Suzanne had said, a lot of fun.

Suzanne said she had picked out a striking deep red nail polish that would accentuate my lips and match my blouse. Okay, I sat down at her makeup station again and she worked her magic on them. She attached nail extensions to each finger and then prepped them for polish. The smell of the glue and polish was not foreign to me, I had been to nail shops before to wait for my girlfriends, but this time it was different. I was the subject of all the attention and it made me feel quite special…like I was being pampered. Suzanne carefully applied the polish and then sealed them once they were dry with a clear gloss polish, which made them shine just like my now full lips.

Now Suzanne pulled out a very beautiful full-length wig. It was exactly the same color as my hair and positioning it onto my head nearly completed my transformation. She brushed it out and made sure the hair fell onto my shoulders and back just right. She then clipped on a set of earrings, which felt wonderful dangling from each ear lobe. She opened the top three buttons on my blouse to expose the natural cleavage formed by my falsies and tight-fitting push-up bra. She fastened a long strand of pearls around my neck to finish off the sultry look.

“Okay, my dear, a little perfume and you’re transformation is complete.” She sprayed Channel #5 on my neck and arms and I felt completely feminized. Then Suzanne walked me back over to her full-length mirror to get a look at her first-time creation. Amazing to say the least! There was no resemblance of my old male self. I was simply and utterly drop-dead gorgeous. This beautiful woman could command the world. God, I was totally hot. I couldn’t believe what a full makeover could yield, but I was truly amazed. From my high heels to my elegant hair I was exquisite. Suzanne simply smiled and said, “I told you not to worry, you’re one-of- a-kind, and totally passable as a woman.”

She had me practice walking in heels until I had the hang of it. I wasn’t embarrassed to be dressed like a woman anymore. I actually was trying my best to show Suzanne I could master the skills of being a woman. She taught me how to sit, stand, and even walk with a slight sashay to exhibit womanly behavior. I was thoroughly enjoying myself…this was so much fun, why hadn’t I done it sooner?

Then we sat on her couch and had a few drinks to celebrate my new persona. Suzanne said, you know, I can’t refer to you as your male name now. You deserve a new name, a very special name. I would let you pick it, but that wouldn’t be fun for me, so how about Amber Lynn.” Amber Lynn sounded very much like a porn star, a slutty bitch I so wanted to emulate. “Sure, I like that a lot,” I said.

“Okay Amber Lynn, do you agree you are a beautiful woman? Do you feel like a beautiful woman? And do you want to totally experience what it really means to be a woman?”

“Yes, Suzanne, I really do want to be a woman tonight, for me and for you.”

With that she leaned over and kissed me ever so softly on the lips. She said, “Okay, then I want you to do me a favor, practice somemore walking in your heels while I go get ready, we are going over to my friend’s house for some drinks. Trust me, everything has been arranged, there will be no surprises, you just act like pretty Amber Lynn and you’ll have a wonderful night to remember.”

I was apprehensive and kept thinking what I could say or do to change her mind. I really didn’t want to change out of my gorgeous outfit just yet, so I reluctantly decided to go along with what she wanted.

Suzanne emerged from her bedroom looking practically identical to me, except she was wearing a one piece and very short and sexy black cocktail dress. Here makeup was dramatic and definitely spoke “I’m hot and you know it.” She had on similar heels and the black belt around her waist accentuated her slim waist and sexy hips and ass. God, she was to die for. We were going to make a scene no matter where we went. Little did I know at that point that my night was going to turn out much differently than I could have ever imagined.

We drove over to her friend’s house and I was getting a little nervous. I had never done something like this before, but Suzanne kept assuring me to remain calm and relaxed. We parked in the drive way out front and walked up the cobblestone steps to the front door. I couldn’t help but notice the pleasant sound of both our sets of heels clicking away as we climbed the last few steps. There we stood, outside a total stranger’s house, both dressed to the hilt as two drop-dead sluts. My heart began beating faster and I felt like turning and running. Just then, the front door opened and I couldn’t believe my eyes. There was a very handsome man standing there and he was apparently very pleased to see us.

“Hello, Suzanne, good evening, please come in and introduce me to your beautiful friend.” I about died right then and there. Suzanne never said anything about her friend being a man; I was expecting it to be another woman. We stepped in and immediately I noticed there was another man there too, a younger man, and equally nice looking. What had I gotten myself into?

“Please come in and sit down you two, I’ll fix you some drinks while we all wait for the roast to get done.” Suzanne introduced me to the two men. The older man was Dante, her sociology teacher from college and the younger man was Mike, an adjunct professor at the university’s school of business.

I sat down in the living room and it was hard for me to relax, what was Suzanne really up to and, more importantly, what was wrong with me, why couldn’t I just get up and leave? Well, for starters, I couldn’t see walking home dressed like a little slut. Second, deep down, I felt this would be an adventure and really wanted to go with the flow of things. Suzanne sensed my predicament and leaned over and whispered into my ear, “I told you that everything has been arranged, just play the part, no harm will come to you.”

Okay, I’ll play the part I thought. I drank two drinks fairly quickly and soon the nerves were somewhat calming. I could see why Suzanne had kept in touch with Dante because he was a very interesting man who had a lot of stories from his many travels around the world. He was in his mid-forties and looked very distinguished with his slight gray accents above his temples. He had definitely kept his body in very good shape. I figured him for a football or basketball player in his younger days and he said, neither, he was into crew and rowed a lot to stay in shape. Mike was equally as athletic looking and he said he was once a star lacrosse player. At 30 he was my age, but looked as if he had just graduated from college.

Conversation was very good and soon I didn’t feel at all nervous about anything. I couldn’t tell if either of these two men knew who I really was, but at this point it really didn’t matter. I truly believed they saw me as Amber Lynn and apparently they were enjoying my company as much as I was enjoying theirs. I now realized what Suzanne had tried to tell me earlier, just play the part and take control of where the night would go.

Dinner was fantastic and Suzanne’s abbreviated feminization lessons had paid off nicely. I knew how to sit, eat, and sip my wine as a woman. I was surprised, but I loved the way I felt dressed up as a woman and how these two men made me feel. I felt desirable, interesting, and sexy. They made no advances in any way and I appreciated their gentlemen manners, I felt totally at ease and safe with them. The wine was working its magic on me and I felt like all my inhibitions were melting away. I was Amber Lynn now.

After dinner, we sat together on the couches and Dante put on some soft jazz for our listening pleasure. I loved his stories and his musky cologne was having an effect on me…it was intoxicating. What was happening to me? I was now having thoughts of kissing this man. He commented on my beautiful look and how he could only dream of kissing such a beautiful and sexy woman. He moved in closer and put his arm around my shoulder. I looked over at Suzanne and she simply smiled and then nodded her approval.

Mike did the same with Suzanne and I watched as she embraced him and then began kissing him, softly at first, then French kissing him. I was turned on by watching the two kiss and grope each other. Dante leaned over and started kissing my neck. Feeling another man’s breath and lips caressing my skin felt surprisingly nice. I didn’t resist in the least. I was Amber Lynn, a woman who wanted so much to explore her new feelings, to act out her new role to its fullest. I turned my head and placed my arm around Dante’s neck. He reached over and gently pinching my chin between his thumb and forefinger, he eased my mouth open. Then he pressed his mouth against mine and inserted his tongue. Gosh, I was putty in his hands. We French kissed for what seemed like an eternity; our tongues twisting and moving about with passion. He caressed my breasts and ran his strong hands over my legs and inner thighs. I didn't object to any of this and in fact, I was so turned on.

Mike had laid Suzanne on her back and had now positioned himself between her legs. He lifted up her dress and was kissing her pussy through her panties. Dante grabbed my hand and placed it on his crotch where I immediately felt his growing erection through the fabric of his trousers. I knew what he wanted and I also knew what I very much wanted to do.

“Could I do it?” I thought to myself; take another man in my mouth? I needed to make a decision because I was quickly reaching the point of no return. I began caressing his cock and kept on kissing him. He then began moaning with pleasure and I decided to please him, no matter what it took.

I got off the couch and dropped to my knees in between his legs. He lay back and closed his eyes. I undid his belt and unzipped his pants. I reached in and released his big cock from his boxers. Reaching under him, I pulled his pants and boxers down and off his legs. He then spread his legs fully and there I was, kneeling down in front of his raging hard-on dressed as a seductive little whore.

I starred at his penis; I had never seen another man’s cock in a state of arousal before in real life. I reached up with my right hand and held him firmly at the base of his shaft. I then lowered my mouth onto him and slowly began sucking his sweet hard cock. I quickly adopted a technique I had seen in a recent porn movie. I stroked his cock and sucked him with my mouth at the same time. I then fondled his balls with my other hand and soon he was breathing heavily. He placed his hands on my head and began guiding my mouth and head to where he wanted me. It was completely erotic to be doing this to another man.

As I was sucking Dante’s cock I could hear Suzanne moaning in pleasure on the opposite couch as Mike vigorously licked away at her clean-shaven pussy. She climaxed and screamed out as intense waves of pleasure surged through her body. Mike then slid his cock into her wet vagina and began fucking her. This went on for a few minutes, then Suzanne said, “Wait, I don’t want you to come in me.”

I turned slightly around to see Mike standing up with Suzanne stroking his very long and firm penis. Then she took him in her mouth and began servicing him just as I was doing to Dante. I continued pleasuring Dante and then I felt someone lift up my skirt and slip and lay them on my backside. My ass was completely exposed and then I felt Mike’s hands pull my gaff to one side. He began licking my rectum and I have to tell you, it about blew my mind. I was enjoying this tremendously. Then I felt him reposition himself as Suzanne squirted lubrication onto the head of his shaft. Then she guided his cock into my tight opening. I gasped, but didn’t stop sucking Dante. I now had picked up the pace and was truly surprised at how good I was at sucking his big cock.

Then Mike pushed his cock past my rectum. The pain was sharp and then I heard Suzanne whisper in my ear to simply relax. I tried my best to relax, but the pain was intense. I winced as he pushed his cock all the way into my ass. He held it there for about a good minute before pulling it back. The pain settled down. I felt completely full with his long and warm penis rammed all the way up my ass. Then he started slowly, then picking up the pace, to fuck me. The pain was quickly replaced with a satisfying feeling of intense pleasure. I felt my own cock begin to fight the restrains of its satin prison. Suzanne’s taping job prevented any growth, but sexually I was going crazy. Having your ass fucked is really a beautiful and sensual feeling that more men should experience. I was ready to come, despite not having a hard-on.

Dante now began trembling and breathing uncontrollably and then he released his load in strong spurts. I gagged on his warm semen quickly filling the back of my throat and mouth. I swallowed several times, not realizing that I unintentionally didn’t want to have his cum ruin my makeup. After all, sluts do have pride in how they look. Dante’s cock began to deflate. I kept sucking gently until he was completely done. I let his limp cock plop out of my mouth and then I bent down and licked up the few drops of come that had spilled onto his thighs and testicles. I was now a true little cock sucker - Amber Lynn the slut - and I loved it with all my heart.

Just then Mike started to pump my ass even harder. I felt his balls slapping up against my ass and he was obviously going to come very soon. He then shouted out, “Oh God, Amber Lynn, your ass is so sweet, I’m coming, I’m coming!” I felt his warm seed begin to fill my ass. It was truly amazing to feel his thick hot cream soothe my sore asshole. He pulled out and then had Suzanne lick him clean. She had no problem with that and finished him off by sucking the rest of his cum from his shrinking penis. I turned around and was totally satisfied that Suzanne and I had sexually pleased these two very hunky men.

We said our goodbyes and drove back to Suzanne’s apartment. Once inside, she said, “You know Amber Lynn my sweet girl, you were the only one tonight who didn’t have an orgasm. Come over here and remove your blouse, skirt, and panties. She then undid the tape holding my cock and balls in place. The feeling of release was very much welcomed. The blood recirculating to my manhood felt wonderful. She had me sit in her makeup chair.

Suzanne removed her dress and panties, then sat on my lap and we began kissing. She was in control and soon my cock was fully erect. She reached down and began stroking me. Her kisses were driving me crazy. She then positioned herself above my cock, guided me into her waiting, wet, and warm pussy. Oh God, I was in heaven. She sank her entire weight onto my lap and my cock was completely enveloped by her tight pussy. She then began rising and falling, fucking me like the dirty little slut that I was. I could taste Dante’s and Mike’s come on our breath and it reminded me of the wonderful time we had tonight. Even though I wished this would never end, I couldn’t hold on any longer. Here I was, dressed as a hot woman, my fantasy come true, getting fucked by this gorgeous woman. I came and came, my cum filling her sweet little cunt. She came at that very moment too and she clamped down hard on my penis. Oh my gosh, this was the best sex I’d ever had!

Suzanne’s insistence that she dress me up as a woman was obviously the missing ingredient in our sex life. If I had known sooner that it would be this intense and pleasurable, I would have given in a long time ago…silly me. Amber Lynn would now be Suzanne’s best girlfriend and certainly, there would be many other encounters with Dante and Mike, for they were now a part of our lives. Yes, Amber Lynn was born and there was no going back.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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