CRUISING for SEX - View Single Post

cyberfree44 · #4 1st June 2006, 10:33 AM

Well, as promised here is my story:

My First Time Crossdressing for a Man

We first met on the internet like so many. As time passed and we shared more and more of our interests and desires, I let him know of my secret fetish to dress in my wife’s clothing. In fact, that I had gone so far as to have hidden away a wig and very realistic breast enhancers. He encouraged me to be more graphic in describing myself when dressed in my wife’s clothes. He told me the more I did the hotter and hornier he became, which didn’t slow down my horniness. In fact, I would crossdress before sitting down to chat with him, which would make me so hard my cock would ache.

During one of our steamier sessions he ask me if I would come to his apartment and crossdress for him. As I was not only a closet CD, but a closet bi person…I guess so closeted that I was a total virgin. Anyway, I agreed not knowing why or even if I would get up the nerve when the time came. We planned the meeting during a time that my wife was going to be away.

My wife isn’t a particularly large woman, but with her slightly stout build and my slim build I am able to get into most of her things. She almost caught me one day when I was laying out what I wanted to wear.

While planning our meeting we decided to do some roleplaying. As he was already a shoe clerk, I would play his last customer of the day. Well, the big day came and I was nervous all day fantasizing about how he would touch me, where he would touch me, how his touch would feel. Finally, the time came and I loaded my women’s clothing into a bag and drove to his apartment. It seemed that I sat out here for an hour getting up my courage, however it was only a few minutes.

I rang his bell, we shook hands and he showed me to the bedroom. We had agreed that we wouldn’t talk that we would just shake hands and then I would dress in private. Making our next encounter with me as a woman. We had decided that I would play being a real woman…not a man crossdressing, if you know what I mean. I can’t tell you how excited and scared I was as I arranged my clothing on his bed and began to undress from my male clothing.
I put on matching black lacy bra, filled with my realistic padding, and bikini panties, dark thigh high nylons, black skirt with a white flowery print and a silky black blouse. I added lipstick and makeup then my expensive and realistic dirty blonde wig. As I looked in the mirror I thought I had never looked so good. I slipped in to my low heal shoes, took a deep breath and opened the bedroom door.

Bill was there with a line of shoes already in place and one of those stools that shoe clerks sit on when fitting you for shoes that he had brought from his store. I could tell from his smile and the way he looked me up and down that he was pleased, which relieved some of my anxiety. He told me that the store was about to close but that he would be happy to help me. He went to the front door and locked it and turned one of those OPEN/CLOSED signs around so it showed OPEN on our side. He came back had me take a seat on his sofa and asked what I was looking for. After a brief discussion he started showing me some shoes.

As he started trying them on and having me walk in them I fell more and more into the part I was playing. Feeling oh so feminine. Then as I sat and he tried on another pair of shoes his hand roamed slightly up the calf of my leg. It was so casual that I almost didn’t notice. With the next pair he casually raised my skirt to my knees so I could get a good look at the shoes. All the time his hands were touching my legs so nonchalantly.

Then with one pair he raised my leg to hold it straight out so I could get a unobstructed look at the shoe and at the same time he was getting an unobstructed look up my skirt. As he lowered my leg, he moved forward and his hand moved just above my knee onto my inner thigh. The touch was like magic and accomplished its intended purpose, as I sucked in my breath and half closed my eyes. I was rapidly starting to feel the passion of his touch.

He looked straight into my eyes as his hand slowly moved up my inner thigh. I finally knew what it felt like to have a man’s hand touching my nylon-clad thigh other than my own. It was unbearable, as much as I tried and wanted to keep myself soft and feminine I became hard as a rock. Then when his hand reached and passed the top of my thigh high and touched my flesh I thought his hand was on fire. I was no longer a man I was a woman filling with passion and desire.

As his hand reached and his finger tips caressed my panties, he moved to the sofa next to me. My skirt was pushed up, you could see my skin above my thigh highs and I could feel his soft, gentle hand starting to fondle me. I was now totally his for the taking. He leaned over and softly kissed my lips. The first time man had kissed me and I was somewhat surprised as I puckered to return the kiss. As his hand began to probe and massage what he called my large clit, his kisses became more intense and before I knew it his tongue was in my mouth and I mine was dancing with his. His hand left my pussy and slowly started unbuttoning my blouse. He pushed it back and fondled my breasts through my bra. I swear I could feel every touch and the tease of my nipples.

As he moved down to my neck, my chest (which is naturally smooth) he rested his cheek against my bosom. Then he went lower and lower tonguing my belly button and slipping past my pushed up skirt to oh so slightly kiss my aching clit through my panties. His lips found the massive wet spot I had created and he kissed and licked at it. I was moaning and swooning like any woman caught up in the ecstasy of the moment. He told me how wonderful I tasted and then I felt his hand start to remove my panties. All I could do was raise my hips to allow them to slip down my legs to the floor. He licked and kissed my clit while both his hands were massaging my breasts through my bra. When he sucked my clit into his mouth I thought I would explode then and there. However, I was able to hold off…how I will never know.

He pulled me down into a flat position on the sofa with me on my back. He kissed down the sensitive under side of my clit and over my thick heavy clit sack. He pushed one leg up and hooked it over the back of the sofa; he raised and spread my other leg with his hand. That is when I felt his hot lips kiss my pussy as his tongue stroked it. I uncontrollably raised my hips off the sofa to meet his wet mouth and let out such a moan that I am sure his neighbors on both sides could hear me. He probed and kissed and licked and I squirmed and moaned and almost lost consciousness the feeling was so intense.

Then he pulled away and stood looking down at me. He started unbuttoning his shirt exposing a well-defined chest covered with black curly hair. As my pussy was still burning from his tongue I watched as he unbuckled his belt, loosened the top button and slowly unzipped his pants. As he let them fall to the floor around his ankles my eyes followed his thick black curly hair down to where it surrounded his hard perturbing cock. He wore no underwear. His cock was average in thickness, but seemed very long and curled upwards. Which seemed so sexy to me as I lay there looking at it and the shiny tip.

He bent down and took a jar from beside the sofa and opened it. He stuck in two fingers, lowered himself to one knee between my legs, as one was now hanging off the sofa onto the floor, and started spreading a warm creamy substance all around my pulsating pussy. I thought I would die when I felt a finger enter me and spread this warmth inside my pussy.

It is funny now but at the time I never really put two and two together. I was just so filled with passion and lust that he could have done anything to me. He leaned forward and kissed me again. I will never forget that kiss, as it was so sweet and loving and tender and passionate all rolled into one. I returned the kiss with every nerve ending in my lips.

He again stood above me and taking the same jar again dipped his fingers and this time spread the warmth over his cock. I could only stare at what seemed like a magnificent tool. He returned the jar to the floor and again placed on knee between my legs on the sofa. He reached down and hooked my one leg that was down off the sofa and raised it up over his shoulder. He leaned forward and again kissed me. Not as softly not as sweetly but with more intensity and lust. This is when I felt it, felt the tip of his cock lightly pushing against the crack of my pussy.

I knew what it was, I knew where it was and for the first time I knew what he wanted. And I knew I was his woman and that I could never say no to him. He whispered in my ear, “Guide it for me.” As if in a trance and completely under the control of this man, I took one hand, found his throbbing rod and placed the tip at the opening of my puckering pussy.

My mind was bombarded with the knowledge that this man was about to fuck me. And even more by the awareness that I wanted him to, that I wanted to give him the ultimate pleasure a man can have, that of inserting his penis into a hot willing pussy. I felt him push and my hands went to his hips to help pull him into me. He stared down at me and I in return stared back up at him. Our eyes locking onto each other and telling the other that this is okay, that this is as close to pure love in one moment that any two individuals will ever encounter.

That is when I felt his nub penetrate my pussy with a shooting pain that for some reason I relished. He saw me wince and paused. But my eyes told him to continue and he slowly started pushing deeper and deeper into me. I never felt more like a woman in my life as I was letting my man have his way with me, giving him my treasure. When he was completely inside me his body fell on top of mine and he kissed me. Not a wild lusting kiss but one of gratitude and love. One that said thank you for allowing me this ultimate pleasure. And then his hips started to move up and down, up and down.

I was being fucked by this man, me who had never even sucked a cock or been sucked before. And I was loving it, I couldn’t get enough. I heard him say, “I want this to go on forever.”

I responded, “Yes, yes never stop never stop fucking me.” I couldn’t believe it, I was even admitting it, saying it out loud that I was being fucked. He would go deep into me and hold it there and I would work his cock with my pussy muscles then he would fuck me some more. It seemed that this went on forever and ever. I was in a state of euphoria.

Then he started quickening his pace, a look of urgency came over his face. He started uttering over and over, “Fuck, fuck, fuck, fuck.” As he pumped my pussy faster and faster. I uttered back at him to let him know it was okay, “Yes, yes, yes, yes.” Then he slammed into me deep, wrapped his arms around me and I could feel him deposit his seed inside my willing and accepting pussy. He was moaning, “I didn’t want to cum, yet.”

I assured him, “It’s okay baby, it’s okay.” As my pussy clamped around his pulsating cock and tried to milk every drop of his goo. I had become so excited at the thought of him cumming inside me and even more so when he did that I never realized until we started to relax that at the tip of my clit was a pool of my own juice being squished between us.

When he finally eased out of me, he took my hand, lead me to his bedroom, finished undressing me except for my thigh highs and bra and we curled up together in his bed. Oh yes, when we did wake up, he did fuck me again. I can’t say that it was as good as the first time, but it and every time after that has been a close second. We don’t always roleplay when we get together, but I always crossdress for him I will always be his woman.