John Learns About Herself Pt. 01

John was 32 years old. He was living with a woman and they had kids but he was not happy. John held a secret: he was a cross-dresser. He had been since a youth and it had grown and surged and waned and returned many times since then.

He didn't really know what he was really. He wasn't attracted to men in the slightest so he wasn't gay but every time he relented and put knickers on, he suddenly wanted to please a man. Well, actually, he wanted to play with a man's cock. The problem was, it would be attached to a man and John knew exactly how much of a dick men could be. There was no love there for men at all... but oh my, the thought of a cock. Now that was enticing. But only when John was dressed in female clothing. It was like putting on another person that took over John's maleness. Even dressed up, he didn't fancy men but he wanted to please them, sexually.

John had had two experiences with men in the past:

The first had come about through an online chatroom whilst he was at work. The bloke was older and just wanted to meet up with John to chat. John was wary for the obvious reasons but he was also not feminine-looking in anyway. Well, yes, he had long hair but he also had a beard and his face was masculine. John thought that would be off-putting to another man: in his head, John was trying to be seen as feminine but I guess other men didn't care about that - ultimately, they just wanted their cock played with. By whomever.

One day, John cracked and agreed to meet up at the local shopping centre at lunchtime. The minutes dragged by until he had to leave work and drive and park up and then walk to the place described by the mystery man online.

Sure enough, the correctly coloured car was waiting in the spot described and John stopped and took a deep breathe before walking up to it and knocking on the passenger window. The window came down and the voice inside said "Get in. We can chat".

John hesitated and then opened the door and climbed in. He turned to the driver and saw an older man, roughly maintained and overweight. Definitely not a turn on.

"Oh well" he thought "we can chat and see what happens, I guess".

They chatted about nothing and then the man finally escalated the situation by suggesting they move to one of the empty parking lots across the road - the business park was in a downturn and companies had closed down and left. The area was fairly quiet now. John agreed.

The ride took all of three minutes and they stopped in a secluded car park behind a building and surrounded by a four foot high hedge. The man unzipped himself and told John to lean over and rub his cock. John refused - he was not feeling feminine in any way and that was needed to desire cock. Right now, he was a bloke in a car with another older bloke. Not conducive to doing this for the first time.

The man was almost wheedling by now. "Just touch it through the material for a bit. It would be a shame to come all this way for nothing. Just a quick feel..." This carried on for a few minutes and John was getting irritated by it, certainly not turned on. But then again, he had touched his own cock so many times that another one, through the material... what was the big deal, really? Wasn't this why he was here? He growled at himself, silently.

Finally, he nodded and sighed and his hand moved hesitantly over, stopping by the gear stick. The man had gone quiet having achieved his goal. He sat there in anticipation.

As John's fingers finally, tentatively, touched the man's groin, feeling the bulge of the cock lurking under the material, the man shuddered and groaned and then apologised profusely. He had come in his pants, already.

John withdrew his hand and muttered pleasantries about it being OK and then said he had to get back to work. He opened the car door and was getting out when the man leaned over and apologised again for the speed of his orgasm. John locked his gaze on the driver and then just nodded and stepped out.

That was John's first experience with a man. In the sexual Halls of Saga, this must rate pretty low down the list. At least for John. The driver probably loved the expectation and the build up and that first touch. It was electric enough to send him over the edge and come in his pants.

John laughed to himself as he walked back to his own car in the shopping complex across the road. "Bloody men" he thought to himself.

Months later, John was back in the chat rooms. He couldn't keep away - it was the only place he could chat as a female version of himself. He had to trawl through the dross of manhood there, trying to find someone he could trust enough to be around as the female him. One day, he struck up a chat with a local man who sounded normal, normal enough to chat with for several days. The bloke was called Tony and he laughed at John as John teased him online... this was something that John was very good at. He knew what men wanted (he was one himself, after all) and how to tease them with that promise.

One day, Tony came out and just said "Come round mine tomorrow and you can dress up for me". John was floored for a moment. This next step had come out of the blue. He paused before replying but finally typed "OK. What time?"

Tony said his wife was out until 4pm so any time well before that. They arranged for noon the next day and John's heart raced at the prospect.

The following day, John left work in plenty of time and drove the short distance across town to Tony's street. He parked his car, collected his bag of clothes and walked down the street before standing before the door, the green door with the number 56 on it. John took a breathe and knocked.

A man, probably in his 40's opened the door and looked John up and down. "You could have shaved" he said.

"My wife doesn't like me smooth-skinned" John lied. He didn't shave because he didn't like shaving - it was too masculine a chore and besides, his skin was always burning red raw afterwards.

"Come in. Do you want a drink? Something to take your nerves away?" Tony offered.

John thought about it and then nodded. "Just a small one - I am driving. Where can I get changed?" he asked.

Tony had disappeared into the kitchen and so John stood in the lounge, looking around at this man's belongings, looking into his life.

Tony came back with a drink and handed it to John. "whisky and coke. OK?"

John nodded and took the drink and sipped it.

"Sit down for a mo." Tony said and indicated the sofa. John sat, taking another sip.

"What is it you want from this?" Tony asked. John looked at him and related the story about the older man in the car and said that was his only experience with a man and no-one had ever seen him dressed as a woman. Tony nodded in the right places and listened. When John stopped, Tony took up the chat with "And you want to dress for me? I am a dominant bloke. I like submissive women. Are you OK with that?"

John merely nodded slightly and took another drink, thinking nervously about the situation. "I need a man to take charge of the situation. If you let me, I will revert back to the male me."

"Good. Go upstairs. The bathroom is at the top of the stairs. You can change there."

John finished the drink in one gulp and stood and left the room, walking up the stairs to then begin undressing and arranging his lingerie. He had his very favourite powder blue padded bra and thong set. He also had sheer hold ups that he liked to wear. He pulled the body-clinging short sparkling dress over his head and pulled it down and straightened it in the mirror: he had found it in a charity shop several years ago and always loved the feel of it and the shortness of it. Finally he pulled on the heeled sandals with their little straps around the foot and ankle. They were only a size 7 but being open toed, his size 9 feet could be forced into them. They were another charity shop find.

John looked at himself in the mirror and gulped. With one final brushing down of the dress, he walked downstairs gingerly and then entered the lounge for the second time.

Tony was standing in the middle of the room and he starred at John, appraising him. "Not bad. But you really should have shaved".

"What do you want me to do?" John asked nervously.

"You haven't ever done anything with a man before? Apart from touching a cock through material?"

John nodded and Tony merely shrugged.

"I want you to turn around and put your hands on the back of that chair. Spread your legs slightly too".

John did as he was told and heard Tony approach and then felt hands on his thighs, rubbing them from knee to just inside the hem of the dress over the stocking material.

"Hang your head down and stick your arse up more". Tony ordered. John obeyed, leaning over as he felt hands running up and over his buttocks. They squeezed his cheeks and a hand ran under, between his legs and around to his belly then back, sliding over his crotch. It was all mater-of-fact and it felt strange knowing that a man was fondling his arse and stroking his groin.

John remained flaccid, much to his satisfaction but he was moving his hips slightly as Tony pawed him roughly, mainly because he had seen women in porn films doing roughly the same sort of thing.

"OK then, come in to the centre of the room and get down on all fours before me. I want you to unzip my trousers now and pull my cock out. Do you understand?"

John's eyes glazed and his breathing came out in heavy breaths. He nodded and knelt on all fours on the carpet, before Tony.

"Good girl. Now get my cock out" he said and John responded hesitantly by unzipping the fly and sliding a hand inside his trousers and under his pants to feel the cock there, swelling already in anticipation of the hand, now resting against it.

He hooked it out and it rose steadily before John's face. John looked at it and then up at Tony. Tony smiled down at him and simply said "Suck it".

John held the cock in his right hand. It was the first cock (apart from his own) that he had ever held. He was so aware of his kneeling position and his clothing against his body and the swelling of the think cock before his face. John blinked slowly, opened his mouth and leant forwards to put that cock into his mouth. He placed it onto his tongue and closed his lips around the shaft, holding the thick cock in his warmth, moist mouth.

John began to suck the cock, trying to do his best. He quickly removed himself from any "oddity" in the situation. He had rationalised it away by think "loads of cocks get sucked every day... people do it and move on... no real issue... that is all I am doing". And so John sucked his first cock, not sure if he was doing anything correctly or badly - he just moved his mouth back and forth and engaged his tongue whilst holding on to the cock with his hand. Tony seemed to enjoy it because he moved his hips and moaned.

John actually didn't mind sucking the cock. It was an OK thing to do - not messy or overly smelly etc. John hissed as Tony took hold of his head in his hand and held his head still as he began to thrust back and forth. The noises were getting messier as Tony's hips moved more vigorously. John occasionally fought the deeper thrusts by pulling back against the hand holding him. "Oh no, you don't, sissy. You are there to take whatever I give you. You don't get to dictate what happens".

With that, Tony thrust harder for a few thrusts and John whimpered at the feel of that much in his mouth. He was gagging occasionally and he hated that but the cock was moving steadily back and forth now and he was still kneeling on his knees with a hand around the cock that was busy at work in his mouth. "I am actually doing it" John thought to himself then. "I am actually being a cock-sucker. A man is hard because of me and I am performing for him". With that, he began to rub the shaft in his hand as it moved inside his mouth and Tony groaned deeper in response.

"That's it baby. Rub my cock. Suck it well baby. Make me come."

John's mind was racing. He was definitely femininely-minded now and enjoying the role-play. He wasn't quite so sure about the prospect of the cock shooting its load into his mouth though but he was still being held by the head and being guided up and down the shaft of Tony's cock which was thrusting nicely into his mouth. He could feel Tony's balls slap against his chin and that spurred him on to wank harder and look up at Tony.

That final bit of the puzzle must have been enough because Tony gripped hard on John's head and thrust deeper into his mouth and his cock changed... John felt the change and then it was spewing out hot, vile tasting liquid that blasted the back of John throat.

John tried to hold it all in his mouth but it was too much and too horrid a feeling to hold. Besides, some had slipped down his throat anyway and he finally gave up and swallowed the rest of the cum. This was not nice but John found himself licking the cock and pulling more of the cum out of the cock even though the taste was not something he enjoyed. He certainly enjoyed making Tony cum though, that was for sure and John's horniness level was well up by now.

He knelt there before this man, with the man's cock in his mouth, licking it clean, having made the man cum. He had swallowed it all and the world was still turning and no-one would ever know... he would leave, dressed as a man, knowing that he had been a sissy for a few moments and had done well.

John thought about that. He could do it again - what would it matter in the big scheme of things? He could be trained to be a good cocksucker, subservient to this man... his thoughts raced.

Tony pulled out and waddled over to the sofa. Not bad for your first time, sissy. I get the impression you liked doing it. Did you?" he asked. John, still kneeling, nodded slyly. Tony laughed. "I bet you are all horny now. My wife is always horny after sucking me off. She always was wet and eager to be fucked. What do you say to that?" Tony asked, looking down at John.

John didn't know what to say. He was certainly horny and had some sense of how Tony's wife felt after sucking his cock. "I can understand that, yes." was all John managed.

Tony laughed "I bet you can." He stared at John in the middle of the floor. "Crawl over here and put my cock away for me."

John obeyed. He liked to obey. He crawl (hopefully sexily) and performed the act for Tony, zipping up the trousers.

"You had better go upstairs and change back into your other clothes - your lunch hour must nearly be over."

John was instantly disappointed and stalled then stood and walked out of the room, back upstairs, back into his male, work clothes.

When he came back down, he said his good-byes and left quickly.

That was John's introduction into the world of being a sissy and pleasing men. It was a long and tortuous and rewarding but costly road.