I hadn’t seen Suzanne in 15 years. She was a member at the country club where my father had worked and, despite living in separate towns, we saw each other every summer. We enjoyed each other’s company and we spent most of our days playing tennis and swimming at the pool.
When I graduated from college and went into the Army, the thoughts of Suzanne were just faraway memories. Then, years later while stationed in Tennessee, I ran into her while out at a local bar. I was amazed at how she had transformed from a skinny schoolgirl into a stunning drop-dead gorgeous woman. She was six feet tall, two inches taller than me, blonde, and had a perfect body. We talked about old times and after a few hours it felt as if we hadn’t spent any time away from each other. We shared stories about past romances and all our experiences away from home. By the end of the night, we decided to see each other again and that was fine with me, she was definitely girlfriend material.
Over the next few weeks, I drove into town from the base to see her. We had dinners together, saw some movies, and went to a comedy show. The attraction was strong between us and I secretly planned a special evening to move the newly-reacquainted relationship to the next level. I was certain her feelings for me were mutual.
As it turned out, her office was having its annual end-of-summer bash and she invited me as her guest. We had a blast and by the end of the evening we were both a little tipsy and looking at each other very provocatively. Suzanne whispered in my ear that she wanted some fresh air and wanted me to join her out on the balcony. I definitely wanted her. Out on the balcony, I made my move and leaned in and gave her a soft kiss on her mouth. She kissed me back and soon we were French kissing and groping each other passionately. Her body was awesome with long lean legs, cute ass, and the perkiest little breasts ever.
Her perfume and perspiration was intoxicating and soon I was sporting a full erection, which she caressed as we grinded against each other. All I could think about was making sweet love to her. She smiled and said “Let’s go home to my place.”
Once we arrived and entered her apartment, it was a mad dash to strip all our clothes off and once again we were entwined in kissing and feeling each other up. We moved our frenzy into her bedroom and we made love for the first time. We fell asleep in each other’s arms and I was truly in heaven.
The next morning we awoke and Suzanne made us breakfast. We had survived the night and it was apparent that the both of us had no issues with becoming more than friends. Sitting across from each other, we talked about our feelings and Suzanne said she had something to tell me that might change everything. What possibly could she say that would change the way I was feeling about her.
She hesitated several times to speak and then her eyes filled with tears. I walked around the table and hugged her. I told her it was okay, I wasn’t going to judge her no matter what she told me and that I had strong feelings for her and wanted very much to be her new boyfriend. She looked up at me and wiping her tears she said she had lost a few boyfriends in the past because of her strange addiction. She said the fetish she held dear was very powerful and it often consumed her thoughts day and night. She said if we were going to take the relationship any further, she wanted to come clean and tell me up front and that if I chose to leave and never see her again, then it was okay with her. Heck, I really liked her and wanted very much to stay with her.
I said, “Okay Suzanne, why don’t you tell me what’s on your mind, I promise to listen.”
Instead, she said, “Follow me; I want to show you something in the spare bedroom.”
In the smaller of the two rooms, Suzanne opened the closet against the far wall. Inside was your typical wardrobe of woman’s clothes: dresses, skirts, blouses, shoes, hats, belts, accessories, etc.
“So, you have a roommate I don’t know about” I said.
“No, I don’t have a roommate and these aren’t my clothes either” she responded.
I was confused to say the least, as I wasn’t quite sure how this wardrobe had anything to do with a fetish. Suzanne sat me on the bed and said that all these clothes were what she had her past boyfriend’s wear when the mood to satisfy her fetish surfaced. Say what! She explained that her fetish was dressing men up, going out with them and then making love to them as a woman afterwards. She said she loved being with men dressed up as women, the more passable they were, the more she got off. I was speechless. Okay, I promised to myself I wouldn’t judge her and that I would keep an open mind.
She remained silent as I pondered exactly what to say. I could sense she was feeling very uncomfortable. After a few minutes of contemplating and deciding I didn’t want to end the relationship that had just started.
I looked into her eyes and said “Suzanne, I understand, I won’t say anything to anyone. If you want to share this with me, I’ll go along, but I’m very leery about going out in public dressed as a woman.”
There was an immediate sigh of relief on Suzanne’s pretty little face and she actually broke into a smile. She said “thanks, I was very nervous to tell you, but felt it was necessary before going any further. I really like you, not only as my friend, but hopefully as my full-time lover.”
I agreed that I wanted that also and that I felt she was very brave for telling me…and that she was a little kinky, which got a huge smile and a laugh.
Suzanne then said, “Okay, this Saturday I’m going to make you dinner, be here at 4pm and I promise you, I’ll make it worth your time and…effort.”
All week I wondered what Suzanne had in store for our Saturday evening. Friday afternoon, she called me at work. After some small talk, she told me to come to her house clean shaven. She said, “If it’s okay with you, please shave your legs, under arms, and chest.”
I was taken aback by her request, but all I could say was “err okay, no problem, I’ll do that.” After all, it was only hair, it would grow back. Shaving my body was definitely strange, but after completing the task and stepping out of the shower, I felt bizarrely alive, a feeling that I had never experienced before. The cooler air of my bedroom against my skin felt nice.
I got dressed in jeans and a T-shirt and drove to Suzanne’s house. As I knocked on her door I thought about what I had really signed up for, what the evening would be like, and would I feel like my old self tomorrow morning. Suzanne opened the door and she about floored me with how hot she looked. She was wearing a tight thigh high pencil skirt, which accentuated her long lean legs. She wore a blood-red sleeveless silk shirt and had a double string of white pearls around her neck. Her legs were adorned with seamed nude-colored hose and a pair of 3-inch black strappy high-heel sandals. Her nails and toes were painted the same blood-red color as her shirt. Her warm smile melted all my apprehensions away.
Stepping into her apartment I could tell she was cooking because something smelled delicious. “My grandmother’s meatballs, they have to simmer another couple of hours, come with me my darling, let’s begin your transformation from caterpillar to butterfly.”
I followed her into the guest bedroom where I noticed she had indeed prepared for my arrival. There were woman’s clothes laid on the bed, her makeup table was fully stocked with lots of cosmetics, and there were several wigs placed out in the open on mannequin heads. She turned to me and said “Do you still want to go along with this or do you have second thoughts?”
I have to admit, my heart was pounding, but I was also a little interested in what I would look like made up like a woman, it was something my older sisters had tried to do with me from time to time growing up, but was never successful. Secretly, I always wondered what it would be like, but would never admit that to them.
“No, I don’t have second thoughts, let’s go ahead and get started; I just hope I don’t turn out to be a disappointment for you.”
She laughed and said, “So far, I’ve never failed in turning a man into a hot woman, you’ll see, I’m very talented.”
Suzanne instructed me to get undressed. It felt a little awkward to get naked in front of her even though we had had sex, but she assured me it would be okay. She looked me over and marveled at the good job I had done in striping my body of hair. She opened a small jar of cream, stepped over to me and began applying the sweet flowery scented lotion to my whole body. My cock immediately responded and she giggled and said that that was completely normal. She then got very serious and said she would take care of that because she couldn't continue with my penis in such a state of arousal.
She got down on her knees in front of me and began stroking me, slowly at first and then faster, but always gently. She then reached onto the nightstand and grabbed an empty wine glass. She pumped my cock faster and faster. Suzanne kept up the pace and soon I was on the verge of coming. She ejaculated all of my semen into the wine glass, which was quite a bit.
She smiled and said “Maybe I’ll have this later for desert.” She definitely had a kinky side to her. Then she wiped me with a baby wipe and once I was cleaned up, she handed me a black satin and lace panty to put on. The feeling of the tight smooth and cool satiny material surrounding my groin and buttocks was intense. Then she grabbed a matching garter belt and secured it around my waist.
As I sat on the edge of the bed, Suzanne unrolled a pair of black lace-topped stockings up my legs and deftly attached them to the four garters. She adjusted the garters and then reached for a black satin and lace bra with a small bow in the front. I lifted up my arms and she slid the bra straps through them and placed the cups of the bra down over my nipples. The bra felt wonderful against my bare chest as she attached the hook and eye closures in the back. She then retrieved a small box from the dresser and produced a pair of nude colored silicone gel false breasts with life-like nipples. She carefully placed them into the each bra cup and adjusted the straps so the breasts hung naturally as a real woman’s would.
The weight of the false breasts tugged slightly on the bra straps and I have to admit, I was enjoying this odd but pleasant sensation. Then Suzanne went over to the closet and pulled out a pair of 4-inch spiked black patent baby doll pumps. I reached for them, but Suzanne said, “No silly girl, you don’t put them on like men’s shoes, you step into them daintily like a princess.”
There was a lot I simply did not know about all this, but I was eager to learn. She placed them side-by-side on the floor in front of me and I placed one foot into a shoe and then the other. I felt like I was teetering on my toes and apparently I was because these heels were tall. Suzanne saw me struggling to maintain my balance and said not to worry; she would give me a class on walking in heels later. She smiled and said “Don’t worry, as much as you’ll be wearing heels with me, you’ll become an expert in no time.”
Then Suzanne, holding my arm, walked me over to her makeup table and sat me down on a nice heavily padded stool. She had all sorts of cosmetics organized neatly and said to be patient as this part would take the longest. She assured me that once she was done, I would not easily recognize myself. She turned me around so I could not see myself in the mirror.
She started by wiping my face clean with a soft moist cloth. She then mixed some foundation into a sponge pad and began applying it to my entire face. She then worked concealer into areas beneath my eyes, above my eye brows, lips, and a little on my chin. She blended it all together using a soft brush and then applied powder with another brush. She kept doing this for what seemed a long time, adding more foundation, more concealer, and then more powder.
Soon she was done and apparently she was satisfied because she then moved onto working on my eyes. She started with adding a light plum eye shadow to my upper lid. She worked the shadow in with yet another brush, then changed to a darker plum color to the creases of my eye lids and then finished with a yet lighter color all the way up to my brow line. She then blended everything together to give it a smooth "smoky" finished look.
Next came liquid eyeliner and she applied a thin line to the top and bottom of my eyes. She was careful not to smudge anything and once again finished blending the liner with a small angled brush. Suzanne then opened a small clear plastic container containing false eyelashes. She applied some clear glue to the rear edges of the falsies, blew on them to get the glue tacky and then pressed them into place. Then she applied a double coat of mascara to the top and bottom lashes of both eyes. When I blinked I could feel their weight and it felt strange, but I wasn’t complaining.
Suzanne then worked on my eyebrows, which she said she had to clean up because they were too thick, but manageable. She plucked away and tweezed beneath them for a good while and once properly shaped she used a dark brown brow pencil to fill them in. She said she extended the edges slightly longer than normal, but that they would wash off with soap and water.
Now, Suzanne turned her attention to my lips. As I have thin lips, she said this part of the transformation would be her greatest challenge, but she stressed that she would transform my lips into a thing of femininity.
She said “All lips are beautiful; you just have to tease the beauty out of them.”
She lined my lips using a deep wine colored lip pencil. She drew the outline carefully on the outer edge of my natural lip line to give the lips a fuller appearance. She then applied a lighter colored lip stick to fill everything in. She used a lipstick brush to blend the two together. To finish them off, she used a clear and very shiny lip gloss to set everything in place. Lastly, she applied some blush to my cheeks and temples. She said, “Not quite ready to show you the results yet my darling.”
I sat there in the chair waiting patiently as she sifted through her jewelry box. The strange feeling and smells of the various makeup products on my face was like nothing I had experienced before. Sitting there wearing a bra with natural-feeling breasts, garter belt and stockings, panties, and high heels made me wonder why dressing up as a woman had never crossed my adult mind before; I was very much enjoying my time with Suzanne despite not being the strong man I always pretended to be. Here I was in her complete control, being feminized and actually having fun. What was happening to me? The night had just really begun and I wasn’t sure where any of this was going to end up, but I was eager to press on, to go where I had never dreamed I could go.
Suzanne returned with some medium-sized clip on gold hooped earrings. She carefully fastened them in place and I immediately felt the slight weight and swivel on each of my lobes.
“Okay, almost there” she said.
She had three wigs on the table and said that we would try each one on to see which one looked the best. The first one was a short bob style brunette wig that framed my face perfectly, but Suzanne said it made me look too serious. The second one was a mid-length auburn wig that had gentle curls that fell neatly about my shoulders, but was not very neat looking. The third wig was the longest, which was brunette with slight highlights throughout, and Suzanne squealed in delight when she saw it on me. It had bangs in front, was layered, and fell to the middle of my back…”perfect” she said.
Suzanne combed it out carefully, twirled some of the hair from the back and put a large very girly-looking brown hair clip to hold it all in place on the back and top of my head. She said my style looked very much like Sarah Palin’s “up-dew” and that I looked very sophisticated, but more importantly, sensual. She said, “you’ll let it down later when the time is right.”
Now Suzanne said we were almost done. She helped me stand up out of the chair and once again, I felt wobbly trying to steady myself on those 4-inch heels. My legs and rear felt slimmer and tighter, perhaps because my calf muscles were working to keep me balanced, but the feeling was nice, I definitely liked the way it felt.
Suzanne then said, “Now my dear, the final touch to your amazing new look. Come over here and tell me which dress you like the most, and don’t be shy.”
She had laid out two black dresses and each was very sexy. The first one was a short style mock wraparound dress with a black belt around the waist with a large gold-colored hoop buckle, which matched my earrings. It had short sleeves and its length was right at the knee. The second dress was also black but had long sleeves. It had a deep-scooped neckline and its length went slightly above the knee. It too had a black belt, but was thinner and more feminine in my opinion. I liked it better because it had long sleeves to cover up the slight hair on my lower arms. Suzanne said her three-tiered sapphire necklace would show beautifully around my neck. Once Suzanne slipped the dress over my head and down onto my body, I noticed I actually had some nice cleavage showing slightly just above the bottom edge of the scoop neck. The lace pushup bra and falsies kept everything in proportion and my bust line looked amazingly real.
I was mesmerized how a simple dress could hide all semblance of my old male form. I loved the way the dress hung and felt on my shoulders, waist, and hips. Suzanne tied off the belt, adjusted the shoulders, and had me spin around to show her how it looked from all angles. When I twirled, the hem of the dress flared slightly outward and I felt wonderfully sexy. I wanted to do it again, but felt somewhat embarrassed to show off in front of Suzanne.
Suzanne then leaned in and sprayed my neck and wrists with Oscar De la renta perfume, her favorite. It smelled wonderful and I immediately felt a growing in my crotch, but the tight fitting satin panties kept me in place and out of the way. Suzanne finished her work by adorning me with three hoop bracelets on my left arm and one dangling diamond bracket on my right as well as a few gold and ruby rings on each hand. I had never worn this much jewelry before and it definitely made a nice touch to my delightful and sexy ensemble.
Then Suzanne said she would now paint my nails. I once again sat down on the makeup stool and handed her my hands. She worked a file over the nails to prep them for nail extensions, which she applied with care. My fingers looked slender with longer nails on them and she said I was lucky because I did not have unsightly men’s hands. I was the runt in my family, the only boy with two sisters and I was cursed with narrow shoulders, slim body, and small feet and hands. I laughed; it was obviously paying off now, wasn’t it? Suzanne then applied a wine colored deep gloss nail polish to each of my nails. They looked amazing. She then completed the job by deftly drawing with a nail polish pencil tiny little flowers on just a few of my nails.
We sat and talked about her old boyfriends while the polish dried. Suzanne explained that each and every one of them walked out on her without as so much as a goodbye…how sad. She said they got tired of her dress-up sessions, even though she satisfied them sexually each and every time. I thought to myself, will I be one of those guys. The way I felt sitting there with her was very strange indeed. It was a rather calming and pleasant feeling deep within my psyche and it scared me a little because I was secretly enjoying being dressed up. Being dressed up all the way like this made me feel that I didn’t have to keep up the act of a being a tough guy, the act that I had never really felt comfortable with. It was all a cover up for the shy little boy that was always there, perhaps it was the little girl in me that longed to express herself, but never had a chance against my strong male dominated persona. What was happening to me?
Suzanne walked me over to the closet door where she had a full length mirror on the back. I now had the chance to take a good look at myself and see Suzanne’s brilliant work. I simply could not believe my eyes, this was surely not me. The person standing there looking back at me was an amazingly hot and sexy young woman. She was beautiful. I now had long luscious and finely shaped legs, nice petite derriere, and firm-looking perky b-cup breasts pushing slightly against the fabric of her “I-know-you-want-to-fuck-me” dress.
She was gorgeous; Suzanne had outdone all my expectations. I never had imagined that she could get me to look this good and convincible. If I ran into this foxy lady at a bar, I could only dream of being with her, she was way out of my league. Somehow, knowing that this was really me, I felt totally empowered in a new and very feminine way. Now I was beginning to understand the power that hot woman possess over men.
Suzanne was beaming with pride. She sensed what I was feeling and thinking and said “I know you said earlier that you did not want to go out in public dressed like a woman, but somehow I think you no longer feel that way…am I right?”
We had dinner and Suzanne was right again, her grandmother’s meatballs were the best I had ever had. Suzanne explained to me how to eat without messing up my makeup. I had to take smaller-than-usual bites and finishing diner took way longer than if I was eating as a man. She also showed me how to sit with my legs either together at the knees or crossed, which was rather hard for me to do as I never sat like that before. I learned how to sip at my wine and dab my lips with a napkin ever so gently after taking bites in order to keep my lipstick from smearing. This was all new to me and I was wondering just how far Suzanne wanted to take all this crossdressing and feminization training.
For now I was okay with it all and told myself to just enjoy the experience, what harm would all this really cause. If I had known what was to come later in the evening, I might have decided right there and then to leave and never return, but in retrospect, Suzanne had done this probably many times before and knew exactly what she was doing…I was putty in her hands.
After dinner, we moved to her living room and I sat down, attempting feebly to cross my legs as she had taught me earlier. It was hard to get my legs to cross tightly and nicely, but Suzanne assured me it would all seem second nature after I had done it a few times. She also taught me how to sit and how to get up from the couch. As promised, she had me walk back and forth in front of her to get used to walking in high heels. She said the trick was to imagine a single line running on the floor and to place each heel on this line as I walked. She said to make sure I extended my leg forward slightly - more than usual - to concentrate on keeping my shoulders and back straight, and most importantly, aiming each heeled foot for that imaginary center line.
She said by doing this I would keep my balance and that my gait would appear womanly. “Take smaller steps and practice, practice, practice. You’ll get the hang of this.”
After about 15 minutes I was able to move about quite nicely in my new pumps and Suzanne was apparently very pleased. She then got off the couch and approached me slowly. She leaned in very close, starred into my purple painted smoky eyes, and kissed me on the lips every so softly. She reached around my waist and ran her hands down my back and onto my rear. She caressed my lower back and buttocks and said that she wanted to give me a new name, a new name she said that would be appropriate for my new feminine persona.
I stammered to get some words out, but she gently placed a finger across my lips to hush me and whispering into my ear, she said “Your new name from now on is Ashley, do you like that name.”
I did like it and somehow it felt proper to have a woman’s name, especially since there was no longer any resemblance of a man in my new look. Suzanne once again smiled and kissed me, but this time she French-kissed me. It felt very peculiar to be kissing a woman being dressed up as a woman, but if this is what it took to have Suzanne for my own, then I would continue to play along.
It was now 8:30 and Suzanne said she really wanted to take me out to celebrate my coming out as Ashley. My heart quickened and sensing I was a little nervous, Suzanne said “Did you not see how beautiful you are in my mirror, you’re simply a knock out, don’t worry, I will never let anything happen to compromise your true identity. We will just go out for a few drinks at a small bar I know and then come back here where I will most certainly want to jump your bones.”
How could I resist, a part of me was scared and confused, but another part, the Ashley part, wanted to go out and let the world see how hot she really was. I thought for a few minutes and said okay and that I trusted her explicitly. Stepping outside into the cool night air and feeling the slight breeze on my hosed legs was electrifying. Girls definitely had it better than men when it came to fashion.
Suzanne held the door open for me and showed me how to properly and daintily enter a car while wearing a dress. “Sit down first and then swing your legs in together as a pair, you’ll get used to it” she said.
We drove to the other part of town, the part I never went because it was simply too far from my house. The bar was called Jack’s Tavern and it seemed lively from the outside. I was starting to perspire with apprehension, but once again, Suzanne was there to quell my fears. We walked in and made our way to a small table in the rear corner near the bathrooms. A slender good looking waitress sashayed over and took our order. She looked at me and smiled, my heart dropped, had I been found out that easily. To my relief, she said “I love your necklace.”
I smiled back and simply whispered in the sultriest voice I could muster, “thanks.”
Suzanne said, “See, I told you everything would be okay, just relax and enjoy the ambiance, it’s not every day that you can go out as another person…a woman, to see what everything is like from a different perspective.“
After two drinks I felt very comfortable, the alcohol from our earlier dinner and now here at Jack’s was working magic on calming my nerves. I looked around and noticed quite a few people were actually enjoying themselves and no one seemed to be staring at me. What a relief. I concentrated on softening up my voice, but Suzanne said my voice was perfect and not to worry too much about that. It felt very good to be this Ashley character and to be with Suzanne, just talking as two girls. I actually thought that this experience was going to be beneficial to me as it would allow me to understand how a woman feels and interacts with her environment.
I had now crossed into unchartered territory, but no matter how much I tried to convince myself I was still a man, my mind and body told me otherwise. I was Ashley, a beautiful young 28-year old woman wanting desperately to explore her new world. The conversation with Suzanne was never better. She surprised me by asking me what I liked in men most.
I sat there contemplating this and she said “Don’t answer this as your old self, answer this as Ashley.”
I totally gave in to this thought and said “I like the way they try to always please you, perhaps it’s because they always want to get into your pants.”
I was shocked, where did this thought truly come from?
Suzanne laughed and said, “It has everything to do with men wanting to get into your pants.”
We were having a great time and all my fears had washed away. Suzanne said “Everyone here tonight sees you as Ashley, you’re probably the only one who knows differently, except for me of course, but once you allow your mind to convince yourself that you are Ashley, you’ll know what it’s truly like to be a woman. Let yourself go, enjoy this, for me, for you, for the both of us.”
Gosh, I was really falling for her. Just then, two young men stepped over to our table, introduced themselves as Brad and Matt, and placed two drinks on the table in front of us. The funny part is I didn’t get nervous as I most certainly would have earlier in the evening. Suzanne introduced the two of us and told them they were very sweet to buy us drinks. Brad sat down next to me and soon we were chatting up a storm. It was funny to see how he was trying hard to get me to laugh at his jokes, doing the same kind of things I had done many times before with girls.
After two more drinks, I was loosed lip and laughing at all his silly talk. Sensing he was doing all right, he leaned in and placed his hand on my knee. He said I was gorgeous and that he wanted to get to know me better. I responded by saying that he was not bad looking either and that his proposition was not entirely out of the question.
Now it was about 1130 and I mentioned to Suzanne that it was getting late. We excused ourselves and went to the lady’s room to reapply our makeup and talk. She asked what I thought about Brad and I said he was, for a man, not bad looking.
She said “Girlfriend, not bad looking, he’s a hunk.”
It was funny to actually hear myself talking about another man in this manner. But then again, I had given into the thought that tonight I was Ashley, the hot looking single girl out to take on the world. We returned to our table and continued our conversations with Brad and Matt. Matt had talked a lot about the city and how as an architect he had recently designed the layout for the community park across the street.
Suzanne thought he was interesting and said that she’d like it for him to show it to her someday. Matt didn’t miss a beat and said “Heck, I can show you it all right now, let’s go for a walk and get some fresh air.”
Suzanne looked at me and said “Is it okay with you, we’ll only be a little while."
I remarkably replied “Okay, no problem, I’m in safe hands with Brad.” What had I just said? ‘I’m in safe hands with Brad.’ Oh my gosh, I had really crossed the threshold into a new, but exciting place. Once Suzanne and Matt left the bar, Brad moved much closer and we talked about his job, my job, which I stretched the truth a bit, and where we all went to college.
I was really feeling comfortable with Brad and he made me feel beautiful and desirable. He was actually a very handsome man, with strong shoulders, nice physique and great masculine features. He probably didn’t have to struggle when it came to seducing woman.
He leaned in close and said, “Ashley, your totally my type of woman, I want to see you again soon. Want to go for a walk?”
We left the bar and walked across the street. I didn’t see Matt and Suzanne, but knew they couldn’t be too far off. Brad then reached for my hand and we walked hand-in hand along the waterfront. I loved the way my heels clicked softly on the sidewalk, the way my dress swayed against my hips, and how my breasts moved up and down with each step I took. It was a beautiful night and I was enjoying myself tremendously. We stopped under a large Maple tree and Brad held me close in his arms. Not surprisingly, I let him. My heart was pounding in my chest; I knew what he was thinking and what was to come next. Would I really allow this to go any further? His cologne was intoxicating and I pressed myself tightly against his firm chest and abs.
He bent his head forward and began kissing my neck. It was intense; I loved every minute of it. His muscular body and boyish good looks made it easy for me to play my new role. He then looked into my eyes and placed his mouth ever so gently onto my lips. He kissed me a few times very softly and then it happened, I reached up and placed my arms around his neck, I was on total auto pilot, no longer in control of my decisions. I was Ashley, the girl who longed to feel the warmth of another man’s mouth.
I willingly opened my mouth and pressed it against his. Our tongues found each other and we French kissed for a while. He ran his hands all over my body and his lust for me was very apparent and very strong. We moved over to a secluded area of the park and we sat down on a park bench to catch our breath.
We then began kissing again and then Brad said “I want so much to come in your mouth Ashley.”
Did I hear that correctly? Kissing Brad was one thing, but giving him head was something I couldn’t do, could I? I had gone somewhere tonight that I never thought was possible just a few short hours earlier. Then it hit me, Suzanne’s words about I was the only one capable of standing in Ashley’s way. Everyone else was convinced Ashley existed, why was I fighting her in my mind? I had made a conscious effort to allow this all to happen, why should I stop now; I had already decided to cross the line when I walked into Suzanne’s apartment earlier that day.
I looked deeply into Brad’s wanting eyes and right then decided I would give into his desires. I got down between his knees and unbuckled his jeans. I slipped the belt away and undid his zipper. He lifted up his hips and I pulled his pants down to his ankles. His penis was fully erect and was sticking out through the opening in his boxer shorts. I pulled his boxers down exposing him totally. Brad was huge as he sported a very thick and long penis. It stood there, at attention, throbbing just inches from my face and wanting mouth. I had never done this before, but I had seen enough porn to know just what to do. I undid his shirt and ran my hands down along his tight chest and abs. He was a hunk, just like Suzanne said; the funny part was I was now just noticing this. Ashley was now in full control.
Before going any further, I reached up and released my hair clip and let the full length of my beautiful hair fall down below and around my shoulders. It was a sensual move that didn’t go unnoticed with Brad.
He said, “Ashley, you turn me on so much.”
I bowed my head forward and kissed the tip of his penis. He had precum oozing and I licked it all off. It didn’t taste bad at all as some of my past girlfriends had mentioned. I was alive with new tantalizing emotions I had never felt before and I liked it very, very much. I was in control now and I understood fully the power we girls have over boys. Brad was powerless and I held all the cards. I decided that there was no turning back; I had completely and fully given into Ashley’s desires to pleasure this man. I then opened my mouth ever so slightly and pushed the head of his penis inside.
I held it for a brief second and then, throwing all caution and inhibitions to the wind, sank my head and mouth all the way down to the base of his shaft. His cock completely filled my mouth and I concentrated on not gagging or dragging my teeth across his soft, but firm flesh. I loved the way it felt in my mouth. I kept my upper lip folded down around my teeth and kept my tongue pressed firmly against the bottom of his shaft. He moaned and I knew I was pleasuring him just the way he liked it. I started out slowly, rising and then dropping my mouth onto his cock.
Steadying myself with my right arm, I reached down with my left hand and gently caressed his balls. I then released his cock from my mouth and switched to sucking each of his testicles. This really had Brad going. I picked up the pace and switched back to sucking him off. The musky smell of his groin and the taste of his cock were exhilarating. Brad’s breathing grew heavier and I knew he was going to come shortly.
I continued to suck him harder and faster. Wow, I was really enjoying sucking my first cock and I thought how I could possibly go on from here without ever doing this again. I was instantly transformed into a cock-loving and cock-sucking bitch. Brad didn’t last much longer. I felt him buck underneath me and then he came. His warm semen spurted into my mouth and unlike all the raunchy sex videos where the girls let it drop from the corners of their mouths, I did my best to swallow all of him.
To get every last drop, I lowered my mouth all the way down and deep throated him. My nose was buried in his soft mound of pubic hair and the last bit of his ejaculation made its way down my throat. His come tasted like nothing I had ever tasted before and surprisingly, I felt like I had accomplished the greatest task in my whole life.
Having finished him off, I reluctantly released him from my wet mouth. As I didn’t want this awesome experience to end, I passionately kissed his softening shaft until he returned to normal size. Brad slumped down in the bench and sighed heavily.
“God, that was fantastic Ashley, you are truly an amazing and talented woman.” I climbed into his lap and kissed him deeply.
We then collected ourselves and walked back to the bar where we linked back up with Suzanne and Matt. We said our goodbyes and Suzanne and I left for her apartment. Now that I had a chance to reflect on what I had done in the park with Brad, I felt a little ashamed.
“Suzanne, I feel like a total slut. I did something I shouldn’t have done, especially on the first night of meeting him, but I couldn’t help it, I wanted very much to go there, to be the woman Ashley really is. Am I wrong for thinking this?”
Suzanne looked me in the eyes and said, “Ashley, you’re a very hot young woman, it’s natural to have those feelings, please don’t let that bother you, you did what you wanted and I’m very proud of you for taking complete control of your new persona. After all, you made a hunky man very happy tonight, aren’t you proud of that?”
She had a way of making me feel good about myself and my decisions. She laughed and said, “Now all I have to do is get you to fix your darn lipstick after giving head.”
I burst out with laughter and I don’t remember the last time I genuinely laughed so hard.
Once back at Suzanne’s apartment, we cuddled on the couch and I recounted how everything went with Brad and how I really liked sucking his big beautiful cock. Suzanne was totally turned on by all this and soon we were kissing and grouping each other. She led the way into her bedroom and laid me on the bed. She reached under my dress and released my penis from its satin prison. She stroked me to full erection, then, unbuttoning and removing her skirt and panties, she exposed the most beautiful site, a neatly trimmed and moist pussy.
She scooted her crotch up to my face and sank her waiting sex onto my mouth. I eagerly kissed, licked, sucked, and probed her vagina with my mouth and tongue. All the time she held my cock firmly in her grip, stroking me up and down. She moaned with excited pleasure and I simply couldn’t get enough. I held onto her hips and ass firmly and licked away…I was in heaven.
Then, without any warning, Suzanne lifted herself from my mouth and lowered her wet pussy slowly onto my erect shaft. She rode up and down on my hard cock for what seemed like an eternity. I reached up, undid her satin blouse, and pushed her bra up to expose her fine breasts. I twirled her firm nipples in my fingers and this sent her over the edge.
She came violently and yelled “Oh God Ashley, I love you, I love you, thank you so much.” I too came at that very moment, exploding deep inside her warm and inviting cunt. She slumped down and lay limply across my body.
She slowly composed herself and then said “We need a drink, would you like to have a drink with me.”
“Sure I said, just one more before ending this wonderful night.”
She smiled in that very seductive way of hers and reached up and retrieved the forgotten wine glass that still held my cum from earlier in the afternoon. She lay down next to me and swirled the ejaculate in the glass as if it were a fine wine.
“Bottoms up my dear Ashley.”
She poured the cum into my waiting mouth and then began kissing me. We indeed shared our final drink of the evening and it was very satisfying to know that I had finally found out who I really was and more importantly, knowing I had a woman who could make all my sweet dreams come true.
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<a href="http://www.lushstories.com/stories/crossdressing/a-night-out-with-suzanne.aspx">A Night Out with Suzanne</a>