Crystal's StorySite


A Life-Changing Experience

by SandraB


Chapter 1

My life has changed forever. Ever since that fateful day almost two months ago, my life has taken a dramatic turn. I no longer have the freedom I once enjoyed. Things I had taken for granted are either gone or drastically changed. The strange thing about it is that I think I am happier than I have ever been before. Let me go back to that day that changed everything.

My wife had gone to her mothers for the day. Usually that meant that I had all of the morning and most of the afternoon to myself. I adored my wife, Abby. She was beautiful, sexy, kind, funny, smart – the entire package. She worked hard to support us as I was working toward a graduate degree. As far as I was concerned, she was as close to perfect as a person can come. But, as much as I loved her, there was still something missing for me. I never told Abby, but ever since I was a little boy, I have been a closeted crossdresser. It started with my mom and sister's clothes when I was young. When I was in college, several times per year, I would pay to have a makeover and crossdressing session with a wonderful lady named Cleo. Once, I even went out on the town with her to visit a gay bar. I freaked out when a guy tried to flirt with me and we hurried out the door. Of course, later I fantasized about what might have been. Abby knows nothing of this part of me. I had resisted for sometime and even convinced myself that I no longer wanted to crossdress. But, lately, I had not been able to stop thinking about it.

Now, with Abby gone, temptation got the best of me. I found myself looking through some of her clothes in the closet wondering what it would be like to wear them. Both my wife and I are very thin, but she is 5'4" and I am 5'11". I knew I would have a hard time finding something that would be a good fit. I decided to start with a pair of black silk panties. They felt so good. I got braver. I slipped on a black dress that Abby had worn recently to a dinner party. I loved that dress. It was short and sexy and looked fabulous on Abby. I looked in the mirror – I had to admit, it did not look so hot on me! But it sure was fun to pretend. I noticed my cock was now at full attention. Oh, how I was loving the feel of the fabrics and imagining myself as a desirable young woman. My name is Steve, but at that moment, I decided to call myself Sandra (after my favorite actress – Sandra Bullock). I slipped on a pair of black boots. My toes had to curl up and it was not very comfortable. But, in my mind, I was Sandra and I was feeling great. I went to my wife's dresser and opened the top drawer. I pulled out a pack of her cigarettes. I don't even smoke, but I have always found that Abby was a sexy as hell smoker. She smoked the long Virginia Slims cigarettes and it was just so feminine and sensual. I found a spare lighter and went to the den. I sat on the sofa with my legs crossed. I opened up the cigarettes and pulled one out. I placed the cigarette between my lips and lit it. I took a deep drag, just the way Abby did when she smoked, and exhaled the smoke. I must admit, I thought it must be an acquired taste, but that it did feel sexy to me. I sat there smoking a cigarette and flipping through some of her Cosmo and Glamour magazines. I was hard as a rock so and I began to rub my cock through the dress. It was then that the inevitable happened…Gwen walked in the door. I never heard the car and I was trapped.

"What the hell are you doing?!", Abby yelled. She stood there with her mouth open and I sat there like a deer caught in head lights. I had nowhere to go and nowhere to run. After several minutes of awkward silence, I tried to explain it away. "It is not what you think", I said. Before I could say anything further, Abby stormed off to our room and slammed the door shut. I could hear her crying. I felt like shit.

After what seemed like an eternity, Abby came back out of the room. By then, I had changed into a t-shirt and shorts that I got out of the dryer. "You have a lot of explaining to do", she said. She continued with barely taking time for breaths between questions, "Do you want to explain why you were wearing my clothes, smoking my cigarettes, looking at my women's magazines? Are you gay or something? How long has this been going on? What does all this mean? I am so confused".

I decided to come clean. I told her about my past, but I also reiterated my love to her and assured her that I was not gay. I told her that beyond that, I cannot really explain it because I did not really understand it myself. I was also confused.

"I am going to stay at my mother's tonight. I need to do some thinking. I will tell mom that you need to work on a paper and can't have any distractions. It will give me some time to sort this thing out", she informed. With that, she threw some stuff in an overnight bag and left.

The next day she arrived at lunch time and seemed to be in a better state of mind. We sat down on sofa together and she looked into my eyes. "I love you", she said, "and I have decided to help you explore this side of you. However, we will only do this my way. Do you understand me?". I said yes I would do whatever she wanted.


Chapter 2

The week went by without much discussion of what had happened. It almost felt like things were back to normal. Abby only worked half a day on Fridays so when I got home from classes, she was already there. "Steve, I picked you up so new clothes. They are lying on the bed. Why don't you go see how they fit", she announced as I walked in the door. Much to my surprise, Abby had purchased a couple of outfits for me, complete with some bras and panties. I could not believe it! "Are you serious?", I shouted back. "You better believe it, buster", she replied, "Try them on". So I did. It felt so wonderful but I was worried at appearing too enthusiastic. What would Abby think? How far will she let me go with this? Was this really happening? My head was spinning.

"Nice fit", Abby said as she walked into our bedroom. "Definitely much better than you wearing MY clothes", she added. She then told me to take them off and to go take a shower. "I am going to come help you take all that yucky body hair off", Abby inserted. I was now getting scared. Sure, I thought about what it would be like to have smooth skin without all this hair, but actually doing it was another thing. But there was something about Abby that was different. It was as if she had become more assertive and controlling. For some reason, I did not argue with her, I just did as she said.

When I got out of the shower, Abby wrapped me up in a pink bathrobe and sat me down at her vanity. She told me to stay still as she did my make-up. It took some time but when she was finished, I could hardly believe the result. There looking back at me in the mirror was a truly feminine face. "Put on your panties", she ordered, "that is, if you can get them over your hard cock". She was right, I was as aroused as I had ever been. She then helped me with my bra and added some breast forms to help me look full. She then helped me slip on the black dress she had purchased for me. "You do like black, don't you Steve", she said, remembering that she caught me wearing her black dress the previous weekend. "What was your girlie name again?", Abby asked. "Sandra", I replied. "Yes, Sandra, my dear…that is what I will call you", she said.

Then Abby brought out a box and opened it on the bed. It was a beautiful brunette wig that she carefully placed on my head. After fiddling with it and brushing it, she led me to the mirror. "What do you think?", she asked. I could not speak. I was overwhelmed. I looked like and attractive young woman. "I must admit", she added, "if I did not see it, I would not believe it. But you are beautiful. No one in a million years would guess that under that layer of femininity is actually a man. Well, at least a semi-man". What did she mean by that last comment I wondered. "You will stay like this", she said. "I am going to teach you the art of being a woman and we will see how much you enjoy it", she added.

That entire weekend, Abby taught me to sit, talk, walk and act like a lady. At one point, she sat me on the sofa and gave a small black purse. In it, she had already placed some make-up – lipstick, blush, eyeliner, etc. Also, she had placed a pack of Virginia Slims Luxury Menthol Lights 120s. She instructed me that over the next week, I was to practice touching up my make up and also smoking cigarettes like a lady. The next weekend, I was informed, we were going on a little adventure. My heart pounded with both fear and excitement.


Chapter 3

When I arrived home Friday afternoon, my wife was waiting for me. She was dressed to kill. She had not dressed this sexy since we were dating. Our luggage was packed and I was instructed to put it in the car and then take a shower. I was also instructed to remove all body hair and that she would help me get dressed. Waiting for me on my bed was my black dress that I had worn around the house the previous weekend. "You looked too good in that dress not to show you off a little bit", Abby yelled from the hallway. A new pair of black high heels were beside, a little higher than what I had become accustomed. Abby walked to see me staring at the shoes. "Don't worry, I have complete confidence that you are going to do great", she said. I was not so sure.

It was almost dark when we left the house. The darkness gave me some comfort and I began to loosen up a bit. I had no idea where we were going. My wife had arranged something for us, and I was not sure what it was. "It will take us a couple of hours, so you just relax", Abby stated. She added, "We will have a late dinner when we get there". I kept imagining that the people that looked into our car would think that there were two attractive young women going out for a night on the town or shopping. At least that is what I hoped they would think. The entire trip, Abby kept giving me a pep talk about acting like a lady and putting in all the things we practiced at home. I practiced talking like a lady, sitting like a lady, and smoking like a lady. I was so nervous but also very excited. In fact, I was probably as excited as I had ever been in my life. Little did I know how soon my world was going to change and that there was no turning back now.

I had figured out we were going to Atlanta, which was only a couple of hours away. Soon, Abby was pulling into the parking lot of Sheraton Hotel in the trendy Buckhead area. Abby went in while I waited in the car. She came back with room keys and a bellman was there eager to help us with our bags. As we made our way down the hall, I noticed that the bellman was checking both of us. I was surprised to discover that Abby had booked separate rooms with and adjoining door between them. "Why did you do that?", I asked. "You will see", was her reply. Then she authoritatively instructed me to ask her no more questions.

She tipped the bellman thanked him for his help. Abby had long ago instructed me to take off my wedding ring because it just looked to masculine to wear when I was being Sandra. But for the first time, I noticed that Abby had removed her wedding ring as well. I started to ask her about before remembering her order not to ask any more questions. "Let's take a few minutes to freshen up before we go to dinner", Abby said to me. "I don't know if I am ready for this", I replied. "Oh, you're ready", she teased back, "I promise you are more than ready."


Chapter 4

As we headed to the door, there was a taxi awaiting us. Abby must have asked the bellman to get us a taxi when they were alone in the hallway. I guess that means we both were going to have a few drinks that night. Abby instructed the taxi driver to take us to Dante's, a jazz club and restaurant which was just down the street. The restaurant had a wonderful ambience about it. We sat at our table and listened to the jazz band playing. We each had a glass of wine before we ordered our dinner. I was so nervous that I did not have much of an appetite, but I knew I should at least eat a little something. After we ordered our dinner, we each had some more wine and smoked a couple of cigarettes. I was really beginning to loosen up a bit and enjoy myself. I leaned over toward Abby and said, "Thank you for this. This is such a thrill for me and I am finally having fun." Abby chuckled, "Oh honey, your evening is only now getting started. You have no idea what is in store for you, or for that matter, for us." The way she said it was frightening. "Abby, what are you talking about?", I asked. Abby leaned closer to me, "Let me explain, my dear"…

When I said, "I do" to you, you were a man. I am a woman and I need a man. When I saw you dressed in my clothes, you ceased to be man to me. Sure, I still love you, but now I can only see you as a girlfriend. I have tried over the last couple of weeks to see you as my husband and a man. When had sex, I tried to enjoy it like I had always enjoyed our sex life. But I could not do it. You are no longer a man to me. However, I still love you, so I have decided to help you fulfill your desires to be a woman. And as a woman, you need a man, just like I need a man.

"I am not gay!", I shouted back, almost drawing attention to ourselves. I even started to cry, but the worst was not over yet. Abby pointed to a guy at the bar. He looked strangely familiar to me. "That is Jeff from work", she said. She continued, "Jeff has always flirted with me but I always rebuffed him because of our marriage. However, because I need a man in my life and you are unable to fulfill that role, I began to return his flirting with some flirting of my own." I began to sink in my seat. As the waiter delivered our food, I thought I was going to loose control and start crying. I gathered my composure and asked, "Have you had sex with him?" Abby did not say a word, she just nodded her head yes. "Last week, when you were studying at the library, I went over to his apartment. I told him all about you and explained my situation to him", she said. "Stop!", I pleaded, "I would rather not hear it." "Suit yourself", Abby said, "but you will have no choice to deal with it soon".

I could not eat. I just sat there staring into oblivion. My whole world was crashing down around me. But it was about to get worse. Abby motioned for Jeff to come over. He said down next to Abby and gave her a kiss. "So, this is Sandra", he said, "It is great to finally meet you." I said nothing. "Well, you are going to see a lot more of me so you might as well get used to it", he added. They began to carry on as if I was not at the table. I kept asking myself, "Why is she doing this to me?"

I got up and went outside. I walked back to the hotel and cried all the way there. I curled up on my bed and wept. A few minutes later I heard Abby and Jeff come it. "Sweetie, you might as well get used to this and get a good attitude about it. I think you may actually discover you will like some of these changes", Abby said. Then she went back through the adjoining door to her room. I could hear her and Jeff laughing and talking. Then I could hear them kissing. These rooms were not very sound proof. Then I heard Abby moaning. They were having sex right next to me as if to make me suffer more. I had never heard Abby scream so much in all of our time together. Was she just putting on a show to humiliate me more or was Jeff really that good? Either way, it was not a pleasant feeling for me.

After a little while, Abby came back in to see me. "I know that was rough on you, but that is just how it is going to be. You need to get used to it Sandra", Abby said. "Besides", she added, "You have a visitor coming in just a moment and the four of us are going back out for drinks". I was speechless. What was she doing to me? As I sat still on the bed, Abby began to reapply my make-up. "Do you feel pretty?", she asked. "Yes", I replied. "Good, because you are very pretty. And I want you to live it up tonight Sandra. Think of this as your 'Coming Out Party'. I have a special friend that I think you are going to really enjoy meeting. He should be here any moment".

I was suddenly terrified again. Abby explained,

After I told Jeff about our situation, he mentioned it to our co-worker Gary. At first I was furious with him for doing that, but the more I thought about it, the more I thought it could be a great thing. Everyone in the office knows that Gary is gay but there is more to Gary than meets the eye. He and I had some long talks over the last couple of weeks. He is such a nice guy and very handsome. It turns out that he is particularly drawn to "girls like you", if you know what I mean. He is a wonderful guy and he wants to meet you. And he will be here in about 5 minutes.

I just looked at her in disbelief. However my cock was getting hard and that did not escape the notice of Abby's watchful eye. "See, I knew you would like the idea", she said. But I still said nothing.


Chapter 5

I heard the knock on the door and I wanted to go and hide, but I had nowhere to go. Abby let him in and after exchanging pleasantries, Gary walked over toward me. "Sandra, it is so nice to meet you. I thought you were beautiful when I first saw the pictures that Abby showed me, but now that I see you in person I find that words cannot truly express just how beautiful you truly are", he said as he looked into my eyes. I really think he meant it and in some strange way in made me feel wonderful, but at the same time I felt scared and awkward.

"Let's go everyone", Abby shouted, "We are all going to ride in Gary's car". Gary grabbed my hand and walked me out the door and down the hall. In the elevator, I watched Jeff put his hands on Abby's waist. He even kissed the back of her neck. Why did he have to do that in front of me? Abby sure seemed to be enjoying herself. Instinctively, I looked at Gary for help. He put is arm around me and gave me a gentle hug. It felt nice to be comforted. He leaned over and whispered in my ear, "I really want to get to know you tonight. Would that be okay with you?". My reply was actually my first words to him and I could hardly believe what they were. "That would be nice", I replied.

As we approached Gary's car, I started to reach out to open the front door. Gary's hand beat me to it as he said, "let me get that for you". I guess I need to get used to things like that. It was kind of nice. We went to a dance club just a couple of miles away. Gary and I sat at the table while Abby and Jeff danced the night away. I was not ready for that and Gary was very understanding. Initially, he did most of the talking. I just sat quietly and listened. I really did find myself liking this guy. He was kind, considerate, funny, and shall I say…charming. I also had to admit that he was very handsome. He was tall and thin but with a more athletic build. He told me he was 35 years old and had been married once before he came to grips with his sexuality. I began to relax a little bit as a drank another glass of wine. I reached into my purse for a cigarette. As I brought it to my lips, Gary reached over with a lighter to offer me a light. As I took that long first drag on my cigarette, I found myself incredibly turned on. He was such gentlemen and he seemed to love treating me like a lady.

Soon, I began to pour my heart out to Gary. I told him about my feelings about my marriage, about my crossdressing, about him. I cried a little and laughed a little too. I guess I was being a typical woman! Through it all, he just listed with his eyes as well as his ears. He had such a look of compassion and understanding. The music suddenly switched to a slower tempo and before I knew it Gary was holding me by the hand and leading me out onto the dance floor. He wrapped his arm around my waist and I instinctively placed my arms around his neck. He pulled me close as we slow danced. I glanced off the side and saw Jeff and Abby dancing. They were looking our way as well with smiles on their faces. Gary reached his hand to my face and guided it back in his direction. "Don't pay attention to them", he said. I stared at Gary's beautiful brown eyes. I began to run my fingers through his hair on the back of his head. He leaned toward me and gently placed his lips onto mine. The kiss was so sweet and gentle and I found myself kissing him in return. It was an incredible moment. My legs became like jelly and I would have fallen on the floor had it not been for Gary's strong arms holding me up. The kiss became more and more passionate and then our mouths opened and our tongues began to explore one another. I knew that life would never be the same and at that moment, I was very happy about it. The song ended and the music returned to the up tempo dance music that had played earlier. I just held onto to Gary's hand as he walked me back to the table. Abby walked by and whispered in my ear, "I just knew you would like Gary". I could not reply. But I knew she was right.

"Why don't we go back to the hotel", Jeff said. As Gary drove us back, Abby and Jeff kissed and ran their hands all over each other in the back seat as if they were high school students. The strange thing about it was that at that moment, I did not care. I just looked over at Gary and held his hand. Abby and Jeff went straight into their room. Gary escorted me to the door and stopped. "Aren't you going to come inside", I asked. "Not unless you invite me", he replied. "I would really like you to come in", I said in return.


Chapter 6

Without saying a word, I took Gary's hand and guided him in front of the bed. I wrapped my arms around his neck as our lips met again. We kissed passionately and deeply. I gently pushed Gary backwards so that he was forced to sit down on the bed. I then began to unbutton his shirt. "Are you sure about this?, he asked. "Oh, I'm sure", I replied. I took off his shirt as he slid his body up to toward the pillows. "How about a message? Would you like that?", I asked. He did not need to answer. I took off his shoes and socks and threw them on the floor. I unzipped his pants, taking a brief moment to feel his hard cock. I pulled his pants off and tossed them on the floor as well. I rolled Gary over and began to massage his shoulders and back. It felt incredible to be touching a man like this, particularly one with such well defined muscles. I sensuously and deeply massaged his arms, shoulders and back. I kissed his neck and ears then I whispered, "Turn over please".

As Gary now lay on his back, I reached down and began to rub his feet. I then worked my way to his calf muscles and then up to his thighs. He gently moaned as I got closer and closer to his big, hard cock. I then began to lick the inside of his thighs. I would circle my tongue so close to his manhood without actually touching it. It was driving him crazy and I loved it. Finally, when I knew he could not take it anymore, I began to suck his balls. Then I slowly ran my tongue up the shaft of his cock. I leaned over and slowly took all of him into my mouth. I could actually feel him getting even harder in my mouth. What a turn on! I began pumping up and down slowly and then I quickened the pace. I placed my right hand at the base of his shaft as I continued to pump and suck. I placed my left hand on his ass and even placed one of my fingers just inside his rectum. Within moments, he let out a moan and filled my mouth with his cum. I eagerly swallowed every bit of it.

Gary immediately took my dress and lifted it up over my head. He pulled down my panties and eagerly took my cock into his mouth. It only took seconds for me to return the favor and fill his mouth with my love juice. Then we laid on the bed together kissing and cuddling. It was fantastic.

As our cocks began to harden again, I whispered into Gary's ear, "I would like you to fuck me". Gary asked if I was sure that is what I wanted. My reply was to stick my tongue into his mouth and my hand on his cock. "Please fuck me", I begged. I reached over into my overnight back for some lube. Gary took it from me and began to rub in on and into my anus. I then placed some on my hands and began to apply it to his hard cock. I knelt over on all fours as Gary got on his knees behind me. He began to tease me by rubbing his cock around my ass. "Fuck me!", I pleaded. He then slowly inserted his cock into my anus. He eased in until he was completely inside of me. Gary began to pump slowly as he reached under me to rub my raging hard on. His fucking began to pick up in pace as did the way he was stroking me. I could hardly believe that a man was inside of me and it made me feel so good. I could tell he was about to come inside of me when my own cock exploded with cum. Within seconds Gary, filled my ass with his cum. We collapsed on the bed together as Gary tenderly caressed my body. It was the best lovemaking I had ever experienced.

Suddenly, Abby opened the connecting door. "Sounds like you two have hit it off just like I knew you would", she said. I looked at her and gave her smile. I silently mouthed the words "thank you" to her. She closed the door and I snuggled up closer to Gary. I knew this is the beginning of beautiful relationship.


The End




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