Be Careful When You Use The Ladies!

Young Ted had a tremendously arousing and sensual experience just two weeks ago and it’s time that you heard about it.

The story begins with the young man walking home from a movie and seeing all the pretty girls going into the nightclubs that line the streets on his way home. At each one, he stopped and looked longingly at the pretty ladies.

He couldn’t help but think of all the fun they were having and all the sex the guys that got to go home with them were no doubt having. If only he could get inside one of those clubs!

crossdressing webcam chats

The reason Ted was at the movie theatre was that they only charged $2 for a ticket and that’s about all he could afford. For a guy to get into one of the night clubs it was a costly $20 and in his broke-ass state he just couldn’t put up the cash.

He didn’t have a job as a 21-year-old college student. His tuition was paid for by his parents and the school gave him money for food as a part of that so he didn’t really have a lot of cash to throw around for fun activities like going to a wild club filled with lots of really hot girls. It was a shame for Ted because there really were tons of super hot ladies in there getting drunk and feeling like they would love nothing more than a hot fuck.

Just as he was about to turn away from the last club to head home young Ted saw a sign that said women got in for free. His first thought was that a policy like that was totally unfair but then he realized he could totally make it work to his advantage.

If there was one thing that had always come up during his school years it was that Ted didn’t look all that manly. He was always being made fun of for having a girly body which guys usually meant that he was really skinny. Sure, he wasn’t muscular but that worked just fine for him and lots of girls liked that look.

Now he was going to embrace his feminine look and get into that nightclub so he could have some fun and maybe get to know some of the ladies.

Ted’s sister was a very sexy girl and she had a closet loaded with stuff that would make him look great. He decided that the only recourse was to go home and ask if she would dress him up for a night at the club. He was sure that she would say yes because she was a nice girl like that.

She loved to help him out and she had a lot of gay friends so it’s not like she would make fun of him for becoming a crossdresser (not that all crossdressers are gay, although before the night was over it would be a question for Ted).

crossdressing webcam chats

Of course, his sister was hesitant at first but she would have been irresponsible if she hadn’t “Are you sure you want to do this Teddy? You’re sort of crossing a line when you put on women’s clothing and try to fool people into believing you’re a girl. You know you’re basically becoming a crossdresser, right?”

“Yeah Crystal, I know. I just want to have some fun tonight, you know? It’s been such a long time since I’ve gone out and really let it all hang out and I think this is the perfect way for me to do that, although of course, I’ll want my man parts to be hidden completely so I don’t want to be literally all hanging out.”

Sissy phone sex chats if you want to discuss all of your crossdressing needs and fantasies

crossdresser picture

Crystal smiled at him and lightly punched him on the shoulder in the way that sisters do. He smiled back and they went about the business of finding him the perfect outfit to get into that club as a crossdressing boy good-looking enough to convince the bouncer and everyone inside that he was a genuine female.

For the top, they settled on a loose and flowing yellow blouse. It was made from an incredibly soft and shimmery material and it hugged his body in a very sexy way.

Call me on my crossdressing phone sex line 

He didn’t really have female curves but the top gave the illusion of them. They went with an orange skirt for the bottom and even though Ted thought the colours would look bad they ended up being perfect together.

His sister thought that a pair of black thigh-high stockings would be the perfect touch, especially since he had a little bit of hair on his legs and that would be a pretty significant giveaway if someone were to spot it.

More sissy phone sex lines here

While putting on the top and skirt Ted had remained sort of distance from the whole situation but when he pulled those stockings up his legs he could feel things begin to stir in the black panties he was wearing. Suddenly he was much more than just a guy dressing up in women’s clothing. He was becoming a genuine crossdresser, which is a whole lot different than someone just pretending.

He was really into it. He liked how the clothes felt on his body and how the simple act of putting them on made him feel feminine. He understood why women liked to wear such delicate little outfits. This was a very good feeling he was having and if being a crossdressing boy is what made him feel that way then he suspected he’d be doing it a whole lot more often.

Once he was in his black stockings his sister took a look at him, “You need just one more thing to be perfect Teddy. I have a little orange scarf that I usually wear with that skirt and if we tie it around your neck it will cover up your Adam’s apple to make sure that there’s no way of knowing you’re a boy under all that sexiness.”

With the scarf applied she brought him into the bathroom to complete his transformation from college boy to college sissy girl by putting on makeup. She started with a little bit of foundation to even out his skin tone.

Then it was some blush on his cheeks, some eyeliner, a little bit of mascara and a thick coat of shiny pink lipstick. She had red in a magazine that guys really like it when the lips are the colour of pussy lips and she tried her best to approximate that with Ted. If he was going to be an effective sissy then he had to be able to fool anyone and if his lips were pink and shiny then no one would be looking too closely at the rest of him.

Once he was all dolled up – they had styled his hair a little bit too – Ted headed back outside and made his way down to the club offering free admission for girls. When he got to the front of the line the bouncer didn’t even bother asking Ted for ID. He just complimented the newly sissified boy on how good he looked, thinking that he was a girl. The bouncer wanted to fuck Ted more than he had wanted to fuck any of the beautiful girls that had come into the club that night.

Inside it was everything he had been hoping for. The music was thumping loudly, the girls were beautiful and he was carried away with dancing and celebrating his newfound freedom and femininity. He loved feeling so girly and he loved that all the ladies in the club were so friendly with him. They clearly thought he was a girl just like them when in fact he was a crossdressing boy trying to fool everyone.

Everything was going perfectly until the sissy crossdresser made a mistake in the bathroom. He got in line for the lady’s room, of course, and when he finally made it into the stall he stood and pulled his dick out of his panties. He should have closed the door but no one else was so he didn’t even think about it. When the girl in the stall next to him flushed and stood up she saw that there was a sissy boy in the women’s bathroom she freaked out.

“What the hell are you doing in here!” she screamed.

She ran out before Ted could even say anything and he figured that if he could get back onto the dance floor and blend in with the rest of the crowd then he would be fine. He didn’t think the girl would tell the bouncer that there was a crossdresser in the club but he was wrong. Just a few minutes later he felt a tap on his shoulder and turned around to see the tall blonde man with the moustache that had let him into the club and complimented him on how good he looked.

Ted was burning with embarrassment at being outed as a sissy crossdresser and he wanted nothing more than to run home. The bouncer was having none of that though. He brought young sissy boy Ted to the back of the club where there was a private bathroom for the employees. He pulled them both inside and locked the door behind them so they would have some alone time.

“I can’t believe you have a cock in their little girl. I could have sworn you were a woman when I let you in. You’re just too good-looking to be a crossdresser. Maybe you’re a woman trapped in a man’s body. I think I know how we can bring the girl inside you all the way out.”

With that, the bouncer unzipped his pants and let his big dick fall out. It was already half hard and Ted’s heart was beating rapidly as he looked down at it and realized what the burly blonde man wanted from him. He was alone in the bathroom, the door was locked and this man was at least twice as strong as him. There was no choice but for him to perform the most humiliating act he could imagine on this well-hung man with a moustache. He would have to get on his knees and suck his dick.

“You’ve got a dick in your panties but mine is much bigger and I know you want to suck on it. Don’t you want to give me a blowjob sissy boy? Wouldn’t my big dick taste good in your mouth? Why don’t you get down there and wrap your lips around it? Become my sissy cocksucker and prove to me that you don’t want to get in trouble for being a little pervert in the bathroom.”

Teddy followed the commands of his new superior and dropped to his knees. His mouth opened and he kissed the cockhead. He started licking it like a lollipop and when he heard the man moan loudly he knew that he was doing the right thing. When he started sucking it felt surprisingly good. A wave of femininity passed through him.  This is what girls must have felt like when they gave their boyfriends and husbands blowjobs. They must have felt this wonderful sense of submission that was running through his body.

“Damn baby, you give good head. That pretty mouth of yours is so warm and tight but your virgin asshole is going to be even tighter and the time has come to pop your cherry. You’re a virgin, aren’t you sissy boy?”

Ted didn’t say anything but instead just grunted his approval. By that point, he had completely submitted to the bouncer and his sexual desires. Now Ted’s job was to serve his needs, to be his fuck hole until the man had blown his hot load.

He pulled Teddy up from his knees and bent him over the bathroom sink. Using a mixture of spit and his precum the bouncer lubed up the young man’s asshole and slid his dick inside. It hurt at first – it’s always painful for a virgin to get fucked up the butt – but Ted was feeling surprisingly relaxed so it didn’t take long for that pain to turn into a nice sense of pleasure. It wasn’t like he was going to cum from getting ass fucked but it wasn’t unpleasant at all.

The bouncer, on the other hand, was in heaven. It had been a long time since his dick had fucked an asshole that tight and beautiful and he was revelling in the fabulous feeling of humping a butt so sexy. Thanks to Ted’s oral ministrations it wasn’t long before his dick was on the verge of cumming and shortly thereafter he let his load loose all over the cutie’s backside. Some of it dripped into his asshole and some of it stuck to the back of his skirt. Now in a daze, Ted was led out the back door of the club and the bouncer patted him on the ass and told him that he was welcome back any time. Do you think Ted went back again the next night? Hell yes!

More crossdressing stories here It’s really time to stop drinking

More crossdressing stories here

Back to Mistress’ Phone Chat Line