Pam and Linda (Their First Encounter)
As a man Jim never felt very attractive, but when he dressed up in as Linda (s)he felt much more alluring. Dressing up on her own soon became a little bit less exciting so Linda bought herself a web cam. This opened up a whole new world of fun she never knew existed.
Suddenly men from all over the world were telling her how sexy she was and all the naughty things they wanted to do to her. She enjoyed the attention and loved to flirt and show off to them even enjoying a little humiliation and domination from some of the more manipulative guys. She found herself experimenting with her own body in ways she would never have left to her own devices. New uses for household and kitchen items were discovered.
Linda's confidence was growing day by day, but there was still that little voice in her head that said "You are a man in a dress, no one really fancies you!" These doubts came in spasms of guilt, but slowly she learned to deal with the fact that the creation of Linda was a way of accepting that she really just wanted to be with a man. One evening while on-line having 'fun' with her web cam, one chatter convinced Linda that she was not only as an attractive cross dresser but could probably pass as a woman also. Linda was hesitant; she had never been out of her bedroom dressed up, never mind out of the house. After much reassurance and persuasion she agreed to dress up in her sexiest outfit, with full make up on and looking very feminine and go out of the house.
Being outside in the cool night air was such a thrill, it was dark so she felt a little more secure, somehow she felt the streetlights helped mask any masculine traits that might show through. Feeling more and more brave and being encouraged by her cam viewers, Linda took a walk down the public street, standing under the street light in her sexy outfit she felt like a hooker. But instead of feeling ashamed she was excited. Her heart was pounding and she had never felt so alive.
Just as she was feeling good about how brave she had been - how coming out of the house dressed up represented a step in her development that is it was coming out in more ways than one, she noticed something that made her heart sink. She felt sick to the pit of her tummy. Someone was watching her and not just from the web cam set up at her house. She couldn't make out whom; she knew the house but not who lived there. Terror had gripped her by now and she hurried back up the street, realising now she was as brave as she had thought.
Hampered by her tight little skirt and inexperience in heels this high, she made limited progress before a voice came out of the darkness behind her. "Hello? Don't run away now, I was so enjoying watching you." it said. Linda was stunned, surprised and confused, what had they said, should she stop, or just get back inside?
"Please, I'd very much like to talk with you." the voice out of the darkened doorway said. Frozen by fear and intrigue, Linda stood shaking from a combination of fear and excitement. Again the voice asked to talk with her and so not wishing to waken the entire street, Linda tentatively tip toed over to the mystery figure.
Blushing intensely, Linda didn't notice at first that the figure in the door way was almost as tall as her, with Linda being almost six feet tall in her flats and nearer six feet three inches in her heels this was a seriously tall person.
"Hello? I'm so sorry if I disturbed you" Linda mumbled looking at her feet, too embarrassed to look the person in the eye.
"Oh disturbed is NOT the words I was thinking of!" replied the figure in the doorway.
"My name is Pam pleased to meet you .....? " smiled the figure in the door way.
"L- Linda " stammered Linda still dying of embarrassment at talking to some one in real time while dressed up.
"Why do you blush so my dear?" asked Pam. Have you never been out dressed before?" she continued.
"No Miss, I m-mean Pam.... I mean...." Linda still shaking mumbled to the ground.
"Miss? Oh I like that, you may call me Miss from now on" Pam giggled.
Feeling a little less self conscious Linda noticed not only was Pam as tall but was dressed in only some pantyhose a very little thong and some very high heels. Nor was she any more a real woman than Linda.
"Why don't you come in out of the cold my dear?" Pam smiled.
Feeling unusually trusting Linda followed Pam into the house. All in all, a very similar house to her own, Linda felt at ease quite quickly almost forgetting she was dressed up. Linda noticed a laptop computer sitting beside where Pam was sitting, on the screen she could see the same chat program that Linda used herself.
"What's your user name?" Linda asked never expecting the reply about to come.
"Pammy69" Pam gigged as she said it - knowing Linda would recognise it as her online friend who had been encouraging her along all this time and was the one who suggested she should come out into the street dressed up. As realization dawned on Linda she felt a little bit used.
"How did you know my user name?" Linda asked
"I didn't dear, but remember that time I made you sit in your bedroom window like a hooker? I looked out this window and saw you - I'll be honest I couldn't believe my luck!" Pam was beaming ear to ear.
"So all these weeks you have seen me coming and going from my house you have known my secret Miss?" Linda blushed again.
"Yes dear, but we did have fun didn't we?" said Pam as she moved over beside Linda and gave her a gentle squeeze.
"Well yes miss - and I did enjoy all the little tasks." Linda smiled wryly as all the naughty degrading things she had done on cam for Pam came flooding back to her mind. All the confessions of her fantasies about being caught dressed up by another CD. Then suddenly Linda realized that this WAS her fantasy. Pam had made her dream come true!
"Can I offer you a drink before we continue?" asked Pam as she stood up and moved to the drinks cabinet. Linda could see Pam's obvious excited state through her pantyhose.
"Continue Miss? How do you mean? I need to go home..." Linda said realizing this was only the start of the evening as far as Pam was concerned.
"Oh now - you are not going to leave me now when you look so pretty and we are finally together just like we talked about. Isn't this exactly what you said you wanted?" Pam smiled pouring two very strong drinks.
The conversation continued on with Linda slowly realizing that this was everything she had ever fantasized about and now was her opportunity to make it a reality. Finally she admitted to Pam that she wanted to be her sub girle. To be there to please her in what ever way was required.
As Linda danced for Pam, as Pam had trained her to do, she slowly stripped down to just her pantyhose bra and wig. As ever the dance ended with Linda on all fours presenting her self. The difference was that this time her mistress was really here and ready to take advantage of the situation.
Pam kneeled down in front of Linda with her pantied cock straining at Linda's lips. Nervously Linda kissed it slowly through the panties and pantyhose. It tasted good and Pam moaned with excitement. Linda went back and kissed it again, but this time pulled the panties out of the way. Again Pam's repose was encouraging.
"Yes I want you to suck me through the hose Linda!" Pam moaned, clearly enjoying the fruits of her weeks of restraint.
Linda wrapped her hand round Pam's thick hard cock and stretched the hose to allow her to suck it better. As she did so the hose split and Pam's cock shot out through them in all its glory. Glistening with precum and saliva.
Linda looked up at Pam and just smiled a naughty smile, clearly she was enjoying this. As she worked the cock into her mouth she was surprised by how big a real cock was - this was much bigger than the dildo Pam had trained her with. The heat of it was a new feeling too. The taste was more familiar after all the precum and cum eating she had been doing in by herself in the previous weeks.
"Deeper Linda! Deeper! I want you to take it all in your slutty little mouth! "Pam moaned as Linda worked it a little deeper on each stoke. Pam using her hands on Linda's face to guide her in terms of stroke and rhythm. Before long Pam was holding Linda's head still and fucking her face, moaning in ecstasy.
As Linda rubbed and squeezed Pam's cream filled sack she felt like the little slut she had always wanted to be. She was happier than she had been in years. But then suddenly Pam stopped, withdrew and told Linda to stand. A little taken aback Linda stood up revealing her own boi clity was very hard and leaking.
"You are enjoying this aren't you dear?" Pam smiled
"Yes miss - very much - but why did you stop miss? Did I do something wrong?" Linda replied.
Pam explained that although it was very good it was not how the evening was going to end. Linda was to experience how it really felt to be fucked. Not the fantasy she had chatted about - but a real cock in her virgin ass. Pam was so gentle, so caring, spending a long time making Linda comfortable with what was to come. She started with a good lube and worked it well in letting Linda get used to someone else sliding a finger inside her.
As Linda moaned in surprise at how good it was feeling Pam slid another one in - then another, pushing them in deep. It didn't hurt it just felt warm and nicely stretched. Then came the dildo, it was BIG. Pam made Linda suck it first; she said it turned her on to watch Linda do that from a distance almost as much as to have her sucking Pam. Then as it slid into Linda she moaned. This did feel good, how could this be? She always heard anal play was sore.
"Yes miss, yes, deeper miss" she begged Pam fro more and writhed in pleasure as it slid deep inside her.
"Are you ready Linda? Are you ready to become my little gurl?" Pam said as she moved round behind Linda, but before she could answer she had pushed the pair of Linda's panties into her mouth.
"This will help you enjoy it even more Linda" Pam explained to her how the lack of air would heighten her climax. Linda could feel Pam's hard cock press against her ass hole.
This was it! Finally the moment Linda had dreamt off for years. As she breathed out Pam's hard cock slipped into her. The feeling was amazing - nothing prepared her for the sensation. Her own boy clitty was leaking a river of precum and with every stroke of Pam's cock in and out of her more and more oozed out. She moaned in delight hoping it would never end as Pam slowly worked deeper and faster. Deeper until Pam's nyloned hips slammed into Linda's ass.
"You like that Linda don't you?" whispered Pam in Linda's ear. Linda unable to answer so just moaned, nodded and writhed pushing back onto Pam's hard cock with each stroke. Finally Pam exploded a river of cum inside Linda's virgin ass. Linda could feel the warm cream being pumped into her. She was so excited her on little boi clit even dribbled out some of its own cum.
"Ohhh yessss!" Pam moaned as her climax seemed to last for at least two minutes. She milked every last drop out inside Linda before slowly pulling out exhausted.
"You are a good girl Linda - now suck me clean and then get dressed and run along home". Pam breathed the words out - clearly tired after all her efforts with her new little bitch.
As Linda walked back up the street, her make up smeared, cum seeping out of her stretched ass, and carrying her panties, she smiled. She finally was the little cum slut she had dreamt off and her mistress was near by so they cud do it all again - soon.