The question "Why crossdress?" still surfaced in my mind on many occasions. At times I struggled to like that side of my nature and in truth there were times when I would rather it was not there. It surfaced though like an addiction, a need and very strong compulsion which I had to give in to.
There were times when I didn't like myself for giving in to this inexplicable desire to pleasure my flesh. When I did give in by ripping off my man clothing and slipping in to lovely, soft, sensual and sexy lingerie I loved it! It was an enigma because when dressed femininely there truly is no feeling like it both inside and out. It had become an obsession I wanted to enjoy as often as I could.
The "story" below is in fact again true although please allow me a degree of latitude with my dialogue, my memory isn't perfect.
Before I start (as I know many of you like to know) I thought I'd tell you what I'm wearing today. Well today is a red day. Fully made up with pale blue eye shadow mascara and red lipstick, a blonde wig which is shoulder length and a short tight fitted red dress. Beneath my dress I have on a red lace thong with matching bra, belt and stockings and of course my four inch stilettoes.
Since the very sexy threesome I had experienced, with Jackie & Shelly, whilst in lingerie I knew I wanted and needed more sexual encounters dressed en femme.
I had started visiting sex chat rooms looking for others of a similar disposition to myself. I dressed sexily then got online eager to chat with hot women or transvestites and cross dressers, on camera if possible. I have always found it very sexually exciting to watch girls & guys pleasuring themselves, so to watch either sex masturbate is such a turn on, it is so erotic.
I have only ever found a very few women willing to share their masturbation but many guys are only too willing to get their dick out and cum with you. This was just what I was looking for yet I wanted more. I wanted it in person, with me, in or out of bed.
Whilst in chat rooms I wasn't bothered whether I found a woman or man to chat on camera with. To see others dressed sexily is always a turn on. To see a woman in panties, with or without a bra with or without stockings is very horny.
To see a dick encased in panties or a hard one framed in lace topped stockings maybe poking out the leg hole of sexy panties is absolutely fabulous. Very often these hot and steamy sessions ended up with mutual masturbation sessions that could be over too quickly. The best ones though were the long languid sensually erotic ones that ended up with me having a self-induced mind blowing climax exploding hot cum over my stockings and panties.
It was excitingly good to cum with others on camera on line but I wanted it for real. I had heard of a place within a secluded part of some woods that was only a slight detour from my usual way home from work. It was a little known dogging site. I thought I would take a look one evening.
It was twilight when I drove up. Just enough light to see what was occurring. I slowed past a couple of parked cars. Two guys were sitting in the front seat of one. They looked over at me and smiled. I returned their smile as I drive slowly by. I parked up a little away from them and looked around.
Not too far away I could see a woman in the back seat of another car bobbing up and down on a guy's knee. It was fairly obvious they were fucking. She was enjoying herself by the look on her face. She knew I had seen her but she appeared not to be bothered and carried on. That was hot.
When I looked back at the car with two guys in it I could only see the driver staring out of the window with sort of a smile on his face. Whilst I was looking around to see where the other guy had gone he sat up and wiped his mouth. He had presumably given the driver a blow job! Well this looked like a good place to hook up.
I looked around carefully and could see others obviously engaged in various sex acts not caring that they were on view. I was getting turned on. I started my car and took a slow drive round taking in what was happening. Everyone appeared at it, except me.
As I drove around the driver of a light green car flashed his lights at me. I ignored it at first and continued cruising round. As I did so a couple of guys came out of the woods and drove away in separate cars shortly followed by a guy and a very attractive woman who also got in different cars. It didn't take much imagination to work out what everyone had been up to.
This certainly was a hot and horny place to be. The car lights flashed again, drawing my attention, so inquisitively I went over to see what the guy wanted. I hoped it was the same as me. I was naïve because this was really my first time anywhere like this. I parked nearby. He asked if I had been here before to which I replied no so he went on further to ask why I was here. I avoided an answer by turning it back on him.
"I'm here hoping for a blow job" he said.
I was surprised with his candor, that he would happily tell someone he had never met his intentions. "So what are you doing here?" he asked.
"I'm meeting someone" I said "we met in a chat room and arranged to meet up" I lied.
He enquired about my sexuality. I didn't know him and was emboldened by his frankness. "I'm a bi-sexual cross dresser" I answered.
This appeared to arouse more interest from him asking me why dressing appealed to me and went on to say he was an admirer of crossdressers.
"Pity you are meeting up with someone" He said, going on to say "I'd love to spend time with you when you are dressed as a female sometime."
"How about meeting here next week?" I said, not really knowing whether I'd have the courage to turn up.
"Next Wednesday then?" he replied. "Will you be cross dressed female?"
"Only lingerie under my clothing as it'll be straight from work but I'll be here" I said, and we agreed to meet a little later in the evening as it would be a bit darker offering us more privacy. We then exchanged phone numbers and agreed to get in touch if either of us couldn't make it.
I was fairly confident I would turn up to meet this guy whose name I didn't even know but my mind kept swinging for and against it. When I was in positive mode my heart raced at the prospect. The week dragged by but finally it was the night before we were to meet. I didn't receive a call to say he wasn't going to be there so excitedly I sent him a text saying I'd be there as arranged. He got straight back saying he could not wait and asked what I'd be wearing. I got back to him and told him it would be a white satin and lace vest top with white lace panties, matching belt and lace topped stockings.
"OMG" he texted back "The thought makes me so horny, I can't wait, I'm hard already"
We agreed to meet where he had been parked previously.
It was the night before a meet I had been waiting for forever. I got some sexy white soft lace panties, matching belt & stockings and a white lace strapped satin vest top sorted out, before going to bed, to wear the next day. I never wore any lingerie to sleep in that night and deliberately hadn't masturbated for a couple of days to make sure I would be extra horny and have a good load to surrender.
In the morning I used hair removal cream on my legs and stomach leaving a nice neat bikini line. I trimmed my pubes short and when my dick was hidden away made me look like I had a pussy.
As always slipping my lingerie and stockings on over my smooth legs was a delightfully erotic sensation. I unrolled my stockings up my legs feeling the sensual fabric caressing my smooth legs as I did so. I fastened the clips on my belt and smiled as I pulled up my panties. I pushed my dick back to hide it from view and held it in place with my tiny pretty panties. I was already getting horny as I pulled my skimpy matching vest top on over my head. I turned around a couple of times admiring the view in the mirror.
I put on my male outer clothes over the top. As always it was a business suit, shirt and tie, boring but underneath my body was in excitement mode. All day long as I tried to concentrate on work my body was in a constant state of semi arousal. The soft panties hugged my dick in a most deliciously sexy and sensual way. The belt, which I had never worn for work before, gripped me lovingly.
A couple of times though the clasps holding my stockings up came undone so I had to escape to the bathroom to do them back up. This gave me opportunity for a chance to fondle myself through my panties maintaining a high degree of arousal.
Sitting down at my desk I was very aware of my stockinged legs. I was becoming so aroused, so excited at the prospect of the evenings adventure. I had pushed my dick back behind me, under my ass, held in place with my panties. This prevented it getting truly hard.
Every time I rested my hands on my legs I became more aware of the stockings I had on. They felt lovely, so sensually lovely! Every time I needed to go to the toilet I caressed my panties and stockings. All of this was a great build up for later in the evening. I could not wait for a guy's hands caressing me through my lingerie.
Finally it was time to leave the office. It was time to meet this good looking guy. It was only a few miles down the road from my workplace so it took no time to get there but all the while I was becoming even more aware I was in lingerie and it was heightening my sensitivity.
The other exciting thought on my mind was for the first time in my life I was going to have another guy's dick. I didn't yet know what I was going to do with it, or he mine, but fuck I was so looking forward to it.
I arrived at the secluded area in the woods and immediately saw the green car where it was parked last week. The autumn light of late evening was fading fast allowing a bit of secluded privacy in the wooded clearing. The silhouetted trees against a darkening sky were a perfect back drop. I flashed my headlights at him as he had done last week. I pulled up between his car and some bushes.
My heart was racing. No sooner had my engine stopped than he was stood in my doorway. He opened my door and leant against the doorpost with a knowing smile. He was average height but his looks were far from average. He was fair haired, blue eyed, broad shouldered and had a friendly smile. He asked if I was well and was I sure I was up for some fun?
"Oh yes" I replied and impatiently asked "Have you had many guys before?"
"Many" he responded" "but I have never had a crossdresser. I've never had a dick gift wrapped in stockings and suspender belt.
"Have you had many guys yourself?" He asked.
"No" I answered, a bit nervously "I've never touched a dick other than my own but to be honest I've been dreaming of doing so for many months."
"So, did you put on the lingerie you promised?" He asked.
"Oh yes" I answered "I want to be dressed feminine whilst I touch my first dick. I want to experience it as a female would."
"Want to show me your lingerie?" He asked "I'd love to see."
"Of course" I answered a little shyly. with that I nervously but excitedly I removed my neck tie, unbuttoned my shirt slowly to reveal my silk and lace vest top.
His eyes took in the view and then reached over to gently stroke my chest and nipples. It felt wonderful. I told him so with which he pinched my nipples softly as if I were a woman. His hand then moved slowly downwards. Lower and lower stroking me in a delicious way all the way down. The lower he got the more turned on I was getting.
His fingers traced along my garter belt, softly feeling along the elasticated fabric.
Our eyes met. "And panties?" he said, looking towards my dick.
"In a hurry?" I asked. "You're keen."
"No but yes, I want a look at you in your stockings and panties" came his reply. With that his hand slipping lower in to my waistband, I sighed with anticipation and pleasure.
"You don't know how long I have waited for a moment like this" I said.
With that I removed his hand and unbuttoned my trousers and pulled them down to my knees. This exposed me in my top, panties and stockings to him. His eyes feasted on me and I loved it. I was still sitting in the drivers seat so I swung my legs round facing outward of the car and reached for him remaining sitting.
I gingerly touched the bulge between his legs. Carefully and sensitively I slowly held his manhood. It was already hard. It excited me so much. I loved the feel of it in my hand. I was enjoying the feel of power over him making him harder the more I massaged it gently. I was enjoying plessing him and the fact he wanted me to.
My dick was trying to get harder too but it was trapped in my panties with me sitting on it wedged between my butt cheeks so it couldn't. However, the feeling of it being trapped in sexy panties fondling another guy's assets were one of the best feelings ever.
As I stroked and fondled his manhood through his clothing he bent forward and sensitively stroked a stockinged leg with each hand. I was in heaven. I unzipped his fly and slipped my hand in but struggled to gain enough access. I had to unbutton his waist band to give me sufficient to get to my intended goal. I lowered his trousers a bit.
As I was lowering his pants he placed the palm of his hand over my panties, where my dick should have been. He pushed his middle finger between my legs and toyed with my dick as if he were rubbing a clitty. This was beginning to drive me wild with desire.
I could wait no longer. I wanted to get my hands on his dick. I had waited too long and was so keen now to have one in my hand and take in the extra special sexiness of it.
"Please leave me a moment" I said. I was afraid he might bring me off before I wanted too. "Let me enjoy your cock first" I said.
I then had his dick fully out in the open. It sprung out in a full erection to full attention standing proud awaiting my attention. I was surprised to see blond pubes. That was a first for me. My heart beat was so high and I was breathless with desire and excitement.
His balls were big and hung below his dick heavily, unlike mine which are smaller, and much tighter in their ball bag.
His dick though was a masterpiece! It was so erect, so hard, so beautiful. It wasn't as long as mine but it had a great width to it. A much greater girth than mine has.
"What is your name?" he asked.
"Suzie" I said.
"Okay my sexy Suzie, enjoy yourself my love" he huskily whispered."
As if I needed any invitation to enjoy a long unfulfilled ambition. I cupped his big heavy balls in my hands as if weighing them. I softly massaged them enjoying the feelings inside my femininely dressed body and mind. His dick twitched as I held it gently with my other hand. In the most sensual way I could I slowly began to wank it, one way, upwards away from his body. Slowly, very slowly and softly, loving the feel of it, repeating my actions, hoping he was enjoying it to the same degree. My other hand found his ass hole which I lovingly fingered.
I wanted to enjoy his fat dick but wanted to please him and pleasure him just as much as I was enjoying it. I wanted us both to enjoy our time together. I was so horny, so turned on that the thought we were outside never even crossed my mind. I was lost enjoying my greatest dream ever.
As I have said before I am petite so have correspondingly small hands. I struggled to get then wrapped around this lovely dick in my hands but I did my very best. I held this wonderful piece of manhood in my hand and slowly began to work it up and down barely holding it just simply trying to tease and pleasure it.
I wanted to make him enjoy his climax but I wanted him to wait for it. I gradually increased my grasp on it and very slowly increased the speed with which I was wanking it. I looked up at his face. His eyes were firmly closed so I guess what I was doing wasn't so bad.
My strokes became faster and faster, then abruptly I stopped, just to tease him more. That was when I stuck two fingers up his ass. He groaned and squated to make it easier for me to get my fingers in him. I began stroking him again a couple of times but again stopped. I was getting him to the brink and holding him there. I was tormenting him.
I had no preconceived notions what I was going to do when I had my first dic. It all just happened naturally. I just held held the base of his lovely dick and licked up his shaft. It dribbled precum. I lapped it up like it was honey. I half opened my mouth and have the tip of it a wet loving kiss.
As I said I hadn't planned any of this but next I found his fat dick in my mouth. I sucked on it greedily, wanking it slowly as I did so. I could barely take it in my mouth it was so big. At first I just sucked and licked at the knob end of it. Then as I got into it I sucked more and more of it. I continued to slowly wank it at the same time. He tried to push it down my throat but it made me choke so I took my mouth away continuing to caress his balls and stroke his shaft.
No sooner had I put it back in my mouth and began sucking away than I tasted someone else's cum for the first time. At first it was a dribble then a gush hit the back of my throat. It was a flood of hot sticky beautiful cum. Wonderful cum. The first time I had tasted anyone's but my own. I licked and sucked away at every last drop not wanting to waste any of his nectar. Now I knew how a woman felt pleasing her lover.
"That was great" he said, "sure you've not done that before?"
"Never even touched one before" I said "I enjoyed it too, glad you did." With that I gave it another caress and a loving kiss.
"So Suzie" he said "Now it's your turn. I am eager to satisfy my first crossdresser."
We changed places. As we did so he removed my shirt fully exposing my silk and lace vest top. I got out of my drivers seat pinching my legs together as I did to keep from having a big bulge in my panties. I kept imy dick tightly squeezed behind me. He sat down in my seat pulling me towards him.
He nuzzled in to my panties stroking and caressing the backs of my stockinged legs. His hands roamed around my sexily clad body, up my silky back, down to my lace covered butt and back down my stockings again. All the while he was kissing and nuzzling my panties. I couldn't believe I was out in the open dressed en femme with a guy, but I only cared about the sexy fun I was having.
He kept one hand behind me pulling me on to him. All the while his other hand was roaming all over my body exploring it whilst sensitively caressing me through my lingerie. He delightfully ran his hands up the back of my stockinged legs and squeezed and stroked my ass cheeks through my panties.
I was lost in the moment. The feelings I was experiencing were like no other and still his hands wandered over my body.
He moved his hand up between my knees, lovingly caressing me through the fine fabric of my stockings, pushing my thighs apart. With that my trousers fell to my ankles. My erection escaped. It pulsated and twitched as it swelled in the front of my panties. He stroked it wonderfully through my panties for a while. And still his other hand worked it's magic behind me.
He removed my stiff clitty lovingly from my panties as gently as if it were made of glass. He pulled them down sufficiently to release it, then caringly pulled them back up, leaving it standing to attention out of the leg hole. He massaged my balls softly through the sheer lace fantastically. He then emulated what I had done to his magnificent dick by softly, slowly caressing it one way, from the base to the tip.
The next treat he gave me was to lightly lick it stopping at the very tip. He licked and softly kissed it making me ache with desire. All the while he was continually exploring the rest of me through my lingerie. I had done this to myself. I had done this to women. Now though I knew just how a woman felt, both to turn a guy on, and to be turned on sensually at the mercy of a guy's caresses.