Sissy Wanted
Sissy Wanted
The ad headline grabbed her attention and her heart skipped a beat. She had only looked at the personals ads to fantasise over the msw section, she never dreamt there would be someone looking for her. She quickly put the idea out of her mind, he may have been looking for a sissy, but that didn't mean he was looking for her. She went back to her fantasies, but those two words kept intruding, and she found herself returning to the ad for a sissy.
It was a simple ad, little more than the headline, and yet it had her heart racing and mind spinning like no other. She kept trying to convince herself that she wasn't ready, not just in her self confidence, but also her appearance, and as convincing as her arguments were, they did little to deter her. Before she realised what she was doing, she had sent a reply to the ad. She wasn't even sure what she had said in the message, and while she began to panic a little, she also knew he wouldn't really be interested in her, so the nerves would only last until he saw her pic. She sat staring at her email, waiting for him to answer, beginning to fantasise about an encounter that would surely never happen, when the message pooped up on her screen indicating a new email.
Her heart fluttered, then she got a hold of herself, he wouldn't have been sitting waiting, the email would be from someone else. She clicked on the link anyway, just to be sure, and there it was, an email from the site with the ad. She clicked on the email, and began to read. The email wasn't much more detailed than the ad, Jamie was looking for a sissy girl to play with, discreet, not at his place, and of course, he wanted to see a pic. He also said he 8 inches, so the length of his email didn't really matter :). As excited as she was to read the email and think about the possibilities, she was also sad now the fantasy was coming to an end. She loaded her photo, pressed send, and waited for the inevitable thanks, but no thanks.
As she expected, the next email did not take long, but what it said blew her away, "Wow you're hot, so when do you want to get together?".
She couldn't believe it and had to reread the email several times and when she was sure it was real, she froze with the realisation that now she would either have to go through with this, or run away and disappoint this nice guy. She took a deep breath and began making arrangements to meet Jamie the next day before he went to work on the night shift. It turned out he lived in the next town, which was actually kind of good as she wasn't sure she wanted to invite guys off the internet around to her home, and she suggested they could go halves in a room, and he jumped at the idea, giving her his phone number and telling her to call him when she was ready for him.
She spent the next hour, or two, looking over motels, weighing up each one before deciding on the most suitable for the occasion and booking a room. Then she had another moment of panic wondering what she was going to wear? She flung open her closet doors and began throwing her hodgepodge collection of women's clothes onto her bed. She tried on every piece on lingerie she had, until she settled on the best fitting, a simple satin bra and panty set. For the rest of her outfit she ended up taking the same approach, the best fit instead of the sexiest/sluttiest, a modest denim skirt and a simple, but cute, everyday top.
After a restless nights sleep she rose early, packed her clothes, and some back up clothes in case she changed her mind or in case Jamie had a preference, and headed off for the hotel. She checked in, drew a hot bath and began to prepare herself for her date. Even though she was nervous, she also had a sense of calm, and even confidence, going through her routine. When she was ready she sent him a message with her room number and waited for him to arrive.
The previous evening Jamie had told her about his sissy Daddy fantasy and she had been practicing her "Hello Daddy" for him, but when he arrived the panic started to set in again, he was quite a bit younger than her, and smaller, daddy just didn't seem quite right. She pushed ahead and greeted him, and while she thought she saw a moment of surprise on his face when he had to look up into her eyes, the small, cute grin when she said "Daddy" drove all fears from her mind and she kissed him, reveling in his returned kiss.
Even though he had Daddy fantasies, Jamie was not as experienced, or as in control as she had hoped, that or she was just really keen to suck his cock. She took the lead, unzipping him, pulling out his rapidly hardening cock and engulfing it, slowly drawing back and letting it slid out of her mouth. Jamie nearly fell over trying to get out of his jeans, so she steadied him and gently raised a foot, taking off one boot, then the other. Jamie then slipped out of his jeans and sat down on the bed while she removed her top. She lent in and resumed sucking Jamie's nice, long cock, while his hands began to slowly explore her body. He was nice, but more of a cute boy than a Daddy, and she had to read his nervous fumbling and assist in the removal of her clothes to keep the momentum flowing. When she had her skirt around her waste and her panties off, he sweetly asked if he could fuck her. She paused from sucking his cock, looked into his eyes and said "Of course Daddy, how do you want me?". She could see the ideas spinning in his head, and since he seemed unsure she crawled around on the bed and offered herself to him doggy style, which seemed to appeal to him. Jamie climbed up behind her and pushed the tip of his cock to her pussy, pausing for a second to check his aim, then pushing inside her, gently but persistently. She encouraged him with some "Oh yeah, fuck me Daddy"'s and he then started to ease into a rhythm, and his role as Daddy. It wasn't long before Jamie pushed her down into the bed, getting her into the position he liked without losing his rhythm. Then he began to really fuck her, long deep thrusts of all 8 inches, and she loved it. He was a little thinner than her perfect cock, but he had the length to make her squeal and squirm. After awhile Jamie fell back into his boyish ways and mumbled some question about cumming, inside her? She wasn't sure of the exact words, and it didn't really matter, so she just said "Oh yeah Daddy, give me your cum", and with that he gave one last thrust and buried his cum deep inside her. He stayed there for a moment or two, gave her a few more thrusts of his cock, and then pulled out of her, collapsing on the bed. She immediately turned and began gently sucking him, cleaning him and using her mouth to massage the last of his cum from his cock. They stayed this way for a while, until Jamie said he had to go to work. She lay on the bed, smiling and watching him dress, and when he was done he reached into his pocket saying "I'd better pay my share of the room" before throwing a couple of notes onto the bed next to her. She smiled widely, grabbed the notes and went to put them with her things, and Jamie laughed saying "I guess that's just reinforcing the stereotype". She laughed too, "Yes" she said "I kind of felt like a whore, it was hot", and she gave a little giggle as she came towards him to kiss him good bye. He kissed her and headed for the door, and just before he left he said, "I'll be back later", and she could feel the glow on her face as she watched him walk away.
The ad headline grabbed her attention and her heart skipped a beat. She had only looked at the personals ads to fantasise over the msw section, she never dreamt there would be someone looking for her. She quickly put the idea out of her mind, he may have been looking for a sissy, but that didn't mean he was looking for her. She went back to her fantasies, but those two words kept intruding, and she found herself returning to the ad for a sissy.
It was a simple ad, little more than the headline, and yet it had her heart racing and mind spinning like no other. She kept trying to convince herself that she wasn't ready, not just in her self confidence, but also her appearance, and as convincing as her arguments were, they did little to deter her. Before she realised what she was doing, she had sent a reply to the ad. She wasn't even sure what she had said in the message, and while she began to panic a little, she also knew he wouldn't really be interested in her, so the nerves would only last until he saw her pic. She sat staring at her email, waiting for him to answer, beginning to fantasise about an encounter that would surely never happen, when the message pooped up on her screen indicating a new email.
Her heart fluttered, then she got a hold of herself, he wouldn't have been sitting waiting, the email would be from someone else. She clicked on the link anyway, just to be sure, and there it was, an email from the site with the ad. She clicked on the email, and began to read. The email wasn't much more detailed than the ad, Jamie was looking for a sissy girl to play with, discreet, not at his place, and of course, he wanted to see a pic. He also said he 8 inches, so the length of his email didn't really matter :). As excited as she was to read the email and think about the possibilities, she was also sad now the fantasy was coming to an end. She loaded her photo, pressed send, and waited for the inevitable thanks, but no thanks.
As she expected, the next email did not take long, but what it said blew her away, "Wow you're hot, so when do you want to get together?".
She couldn't believe it and had to reread the email several times and when she was sure it was real, she froze with the realisation that now she would either have to go through with this, or run away and disappoint this nice guy. She took a deep breath and began making arrangements to meet Jamie the next day before he went to work on the night shift. It turned out he lived in the next town, which was actually kind of good as she wasn't sure she wanted to invite guys off the internet around to her home, and she suggested they could go halves in a room, and he jumped at the idea, giving her his phone number and telling her to call him when she was ready for him.
She spent the next hour, or two, looking over motels, weighing up each one before deciding on the most suitable for the occasion and booking a room. Then she had another moment of panic wondering what she was going to wear? She flung open her closet doors and began throwing her hodgepodge collection of women's clothes onto her bed. She tried on every piece on lingerie she had, until she settled on the best fitting, a simple satin bra and panty set. For the rest of her outfit she ended up taking the same approach, the best fit instead of the sexiest/sluttiest, a modest denim skirt and a simple, but cute, everyday top.
After a restless nights sleep she rose early, packed her clothes, and some back up clothes in case she changed her mind or in case Jamie had a preference, and headed off for the hotel. She checked in, drew a hot bath and began to prepare herself for her date. Even though she was nervous, she also had a sense of calm, and even confidence, going through her routine. When she was ready she sent him a message with her room number and waited for him to arrive.
The previous evening Jamie had told her about his sissy Daddy fantasy and she had been practicing her "Hello Daddy" for him, but when he arrived the panic started to set in again, he was quite a bit younger than her, and smaller, daddy just didn't seem quite right. She pushed ahead and greeted him, and while she thought she saw a moment of surprise on his face when he had to look up into her eyes, the small, cute grin when she said "Daddy" drove all fears from her mind and she kissed him, reveling in his returned kiss.
Even though he had Daddy fantasies, Jamie was not as experienced, or as in control as she had hoped, that or she was just really keen to suck his cock. She took the lead, unzipping him, pulling out his rapidly hardening cock and engulfing it, slowly drawing back and letting it slid out of her mouth. Jamie nearly fell over trying to get out of his jeans, so she steadied him and gently raised a foot, taking off one boot, then the other. Jamie then slipped out of his jeans and sat down on the bed while she removed her top. She lent in and resumed sucking Jamie's nice, long cock, while his hands began to slowly explore her body. He was nice, but more of a cute boy than a Daddy, and she had to read his nervous fumbling and assist in the removal of her clothes to keep the momentum flowing. When she had her skirt around her waste and her panties off, he sweetly asked if he could fuck her. She paused from sucking his cock, looked into his eyes and said "Of course Daddy, how do you want me?". She could see the ideas spinning in his head, and since he seemed unsure she crawled around on the bed and offered herself to him doggy style, which seemed to appeal to him. Jamie climbed up behind her and pushed the tip of his cock to her pussy, pausing for a second to check his aim, then pushing inside her, gently but persistently. She encouraged him with some "Oh yeah, fuck me Daddy"'s and he then started to ease into a rhythm, and his role as Daddy. It wasn't long before Jamie pushed her down into the bed, getting her into the position he liked without losing his rhythm. Then he began to really fuck her, long deep thrusts of all 8 inches, and she loved it. He was a little thinner than her perfect cock, but he had the length to make her squeal and squirm. After awhile Jamie fell back into his boyish ways and mumbled some question about cumming, inside her? She wasn't sure of the exact words, and it didn't really matter, so she just said "Oh yeah Daddy, give me your cum", and with that he gave one last thrust and buried his cum deep inside her. He stayed there for a moment or two, gave her a few more thrusts of his cock, and then pulled out of her, collapsing on the bed. She immediately turned and began gently sucking him, cleaning him and using her mouth to massage the last of his cum from his cock. They stayed this way for a while, until Jamie said he had to go to work. She lay on the bed, smiling and watching him dress, and when he was done he reached into his pocket saying "I'd better pay my share of the room" before throwing a couple of notes onto the bed next to her. She smiled widely, grabbed the notes and went to put them with her things, and Jamie laughed saying "I guess that's just reinforcing the stereotype". She laughed too, "Yes" she said "I kind of felt like a whore, it was hot", and she gave a little giggle as she came towards him to kiss him good bye. He kissed her and headed for the door, and just before he left he said, "I'll be back later", and she could feel the glow on her face as she watched him walk away.
11 years ago
Very hot !
Loved reading about your sexy encounter,
xxx