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Old 07-17-2017, 07:29 PM
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zoy662 zoy662 is offline
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Default Strap-on takes cross-dressers virginity.

Sorry if this sucks. Its my first story.

Zane had never really considered himself a submissive or dom or anything like that. He really didn't have much of a sex life, in fact he was a virgin with no sex life. He always watched a fair amount of porn buy it was always pretty basic “guy fucks girl” type stuff. The most exciting thing about Zane was that he was a crossdresser who exclusively wore Bras and Panties, in fact when moving to Chicago he left all of his old boy underwear behind, however this was more of a comfort thing than a sexual thing.
Zane was a pretty lonely guy and hadn't really met anybody since the move two months ago, but he decided he wouldn't just spend all of his time in his apartment. Zane bought tickets to a comedy show at a club he arrived a little late so he ended up sitting at the bar, not that he could drink being only 19.
The show had ended but Zane hung around for a bit to finish his coke. Then she walked u and sat right next to Zane. She was a very beautiful woman, standing at 5’5 compared to zane who was an even 6 foot. Her hair was black and curly, her skin was olive, and her eyes were a beautiful brown. Zane hated to think this way but if he didn't hear her talk he would have assumed she had just came from Israel. She was wearing a pair of new looking black jeans with a light blue sweater.
She looked at Zane a moment then spoke, “I love your outfit”
Zane took a moment to study his apparel, it was nothing special just old blue jeans and a t shirt depicting The Who. Still he was happy this beautiful girl was speaking to him. “Uh, thanks” He said.
“You know what my favorite part is”
“No” Zane asked confused
“The pink bra strap hanging out of your shirt” She said pointing to what was obviously a bright pink bra strap.
Zane was absolutely horrified. He could not believe this beautiful girl had just discovered his most embarrassing secret. He immediately covered it up with his shirt. He felt like such an idiot for letting this happen. He couldn't bear to look at this beautiful girl in the eye and he stared at the floor.
She spoke up “Usually when someone gives you a compliment you're supposed to say ‘thank you’”.
Zane spoke still looking at the floor. “Thanks” His words were barely audible.
“Are you embarrassed” She spoke loud and clear. Zane remained silent, and she grabbed her head by the chin and lifted his head until he met her eyes. “Hi. I asked you a question. It's very rude to ignore people like this” He still said nothing, he was completely awe struck that she had discovered his bra and that she kept talking about it. “Well?” she asked again, “Are you embarrassed or not?”
Zane decided he might as well speak, “Yes, I'm embarrassed.”
“Holy shit!” she replied, “He fucking speaks” At this point she let go of Zanes head. “I’m Suzie.”
“Zane” he said still confused as to what was going on.
“So Zane, are you wearing panties?”
He could not believe she had just asked him this. Of course he was wearing panties, he always wore panties, but he could never admit it. “Um, uh, what?”
“I said. Are you wearing panties?” Suzie respond, each word clear and purposeful.
Zane was in a state of shock. “Um, I don't, uh, I um...”
“ Are you trying to say you don't know?” She said, mockingly. “How can you not know if you’re wearing panties? You do know what panties are right? They’re girl underwear”
Zane started to notice people beginning to look at them and his face flushed with red. “Um could you not, uh talk so loud”
“Um uh uh uh durr um durr” she said clearly mocking Zane and his nervousness. “I understand if you're shy or whatever, but God, grow a fucking dick. Just answer the question and stop acting like a bitch”
Being berated like that snapped Zane out of his fog and he spoke to Suzie, “Yes”
“Yes what?”
He began to blush more than he thought possible. “Yes, I'm wearing panties”
A big grin appeared on her face, “I knew it. Well lets see them.” Zane did not move, he couldn't imagine what he was expected to do. “God, do I have to do everything?” she asked, annoyed. She grabbed the side of his jeans and pulled down enough to expose the purple lace material of Zanes underwear. “Sexy” She let go of the jeans and Zane moved to cover his panties back up. “Come on we're going to my place” She lead Zane by the hand out of the club.
Zane could not believe this was happening. First a beautiful girl discovered he was a crossdresser now they're in a lyft heading back to her apartment. The two remained silent until Suzie lead him through the door into her apartment. She lived on the fifth floor of seven in building downtown. It was very tidy, much cleaner than Zanes messy studio in the south side. The apartment had two bedrooms, a kitchen, a bathroom with tub and shower, and a spacious living room where the two stood now.
Suzie walked Zane to the center of the room and stood facing him. “Alright.” she said. “Strip down to your underwear”
This is not how Zane expected his night to go. “Right now?” he asked.
“Yes right now.” She responded, “What the fuck do you think I brought you here for?” With that Zane pulled his shirt over his head revealing his bright pink bralette with green cups splayed with floral patterns. He went to work on his jeans and undid the button. He pulled his zipper and lowered his jeans before slipping them off his feet. His purple crochet lace boyshorts were now completely revealed. “Glad to see you're enjoying yourself.” She said eyeing his dick. He looked down and realized he was hard. When did that happen? How could he not have noticed? “Shame about the size though” That hit Zane hard like a punch in the gut. He knew his dick wasn't big, when he measured he found he was 1.5 inches soft, and just under three inches hard, but he didn't expect the first girl to see it to make fun of it. “Take your underwear off, now.” Zane stripped naked and stood in front of Suzie.
Suzie stood looking at Zane almost disappointed. “Wait right here” with that Suzie went off into the other room for what seemed like hours why Zane stood there with his mind racing. Suzie returned from the other room dressed very differently. She was almost completely naked, the first thing Zane noticed was her beautiful olive breast he could have spent days staring at them if he wasn't distracted by the dildo strapped to her waist. Zane's heart dropped into her stomach when he saw that. She was crazy there was no way she thought she would actually use that on him. The dildo was a very realistic white cut cock that was 5 inches long and thick enough that you couldn't wrap your whole hand around it.
“What is that?” He asked already knowing the answer.
“It's a strap on” She answered matter o factly.
“What are you going to do with it?” He asked already fearing the answer.
A big smile came to her face and she spoke with complete authority, “I'm going to fuck you with it”
Needless to say Zane had never had anything up his ass before and he was terrified at the thought of that being jammed up him. “Fuck you, you're not doing that”
She walked over to Zane and placed her hand on his cheek, directing his eyes to hers, “I understand the idea of being fucked for the first time is scary, I've been there, but your dick is tiny and there is no way I'm going to get any pleasure from that. This dildo has a vibrator in the end so I can get off, and you are going to love being fucked so you can get off, and if you're still not into it you can get out. So make a choice”
Zane was terrified but he really liked this girl and he was actually enjoying how she was treating her. Was it worth taking it up the ass though? Fuck it. “I'll do it”
Suzie pinched Zane’s cheek in between her thumb and pointer. “Good girl”
Zane blushed, “I’m not..”
“Quiet now” Suzie cut him off. Zane immediately closed his mouth, he would have to talk to her later. “It's important that you listen to what I say so this goes as smoothly as possible for you, now get on all fours with your ass in the air and your cheek against the floor”
Zane looked down at the tile floor. It didn't look very comfortable and was hoping for something better for his first time. “Couldn't we use your bed and or at least your couch?”
Suzie looked annoyed, “ I dont want cum stains on my sheets or couch, now get on the fucking floor”, With that Suzie smacked Zane hard on his ass making him jump and squeal. He followed her instructions and knelt down with his face on the tile and his ass as high in the air as he could get it. “Stay right there, I'll go grab some lube” Zane could not believe the position he was in, this was without a doubt the most demeaned he had ever felt, and had she really spanked him? I mean a light slap is fun but this was really hard, He could still feel the sting. He heard Suzie come back into the room, he wasn't able to see much from the position he was in. He then felt something old and wet against his asshole that made him jump. “Calm down”, suzie said comforting, “I'm just lubing you up, trust me you don't want me going in dry” Suzies started applying pressure with her finger to his asshole, “I'm going to start fingering you now, to loosen you up” Zane felt her finger slip into his asshole his immediate reaction was to clench up, Suzie slapped his ass again, harder than before. “Don't clench up, It's just going to make this hurt”
Zane was a little angry now, “Don't fucking hit me”
“First off” Suzie began, “ I didn't hit you, I spanked you, there's a difference. Second, I wouldn't have to spank you if you would be a good girl”
Zane was very annoyed now, “I'm not a fucking...”
Suzie stopped him, “No more talking”
Suzie worked her finger back into Zane’s asshole, It was without a doubt the strangest thing he had ever experienced. At the same time it began to feel good, like pretty good actually. Although it was difficult to fight his instinct of clenching he made sure not too as he could still feel the pain in his ass. The fingering continued on for a time when Zane felt a second finger slide inside him and let a moan escape from his mouth as he got filled with Suzies fingers. This time she was a bit rougher and finger fucked his ass with much forces. Zane found himself almost whimpering as she took her fingers out. Zane felt something big and wet press against his asshole.
Suzie spoke,”Ok this is going to hurt a bit, but you just gotta breath through it”
The dildo entered Zane and a harsh stinging pain began in his ass. “Ow, fuck, fuck, fuck!” He screamed as he pulled away from the dildo.
Suzie beat his ass hard, three times, Zane let out a loud shout. Suzie grabbed Zanes hair hand pulled his head towards her. “Don’t you ever fucking pull away from me like that again. Do you understand me?” Zane felt ashamed he was letting himself be treated like this so much all he could do was nod his head. “Good” Suzie stated, and slided Zane back across the floor by his hips.
He again felt as the dildo worked his way into his ass there was pain but Zane knew better now than to try and pull away. He squirmed a little as the dildo entered him. He felt the movement in him stop. “The tip is in now, I'm going to let it sit there as you stretch out”
Zane was in much pain, “That's just the tip? It hurts so fuking much”
“I told you it would.” Suzie reminded him. “Now stop fucking whining, It's really annoying.”
Zane realized how much complaining he had been doing and decided he would stop.
“Ok we're going to do more now” Suzie said as she began working the didlo deeper and deeper into him. Zane could do nothing but lie there moaning as all five inches were driven into his ass. It felt fucking amazing, this was the greatest thing he's ever experienced. Slowly Suzie drew away from him, then slowly pushed back in. She repeated this action gaining speed each time. More moans escaped from Zane and he realized that he was actually being fucked. He always dreamed and fantasized that he would have his virginity taken by a beautiful woman, however never did he think it would involve being fucked up the ass.
Zane’s cock began aching, and he wrapped his hand around his whole dick and started stroking. Moan after moan leap out of Zanes mouth as this girl pounded his, he couldn't take it anymore and shot a hot white load of cum from his now shrinking dick. After his orgaam he began to focus more on Suzie who was still fucking him. He realized she was moaning and had been the whole time, she began to fuck him harder and harder as her breath began to skip. She thrust once hard and deep into him while she had an intense orgasam. She pulled out and they both lie there gasping for air.
Suzie turned to Zane, and again pinched his cheek. “Good girl, very good girl”
If he hadn’t just had the most satisifying orgasam of his life he would have been much more angry about that. He barely said a word before Suzie pointed to his cum on the floor and ordered him to clean his mess. He wiped it up with some napkins from the kitchen. Zane started to gather up his clothes and get dressed when he found something missing. “Umm, have you seen my panties?” He asked Suzie.
“Yes I have” she responded, still lying on the floor.
“Where are they”
“I’m keeping them as a trophy”
“I really like that pair” Zane said, meaning it.
“Are you doing anything tomorrow?” Suzie asked
“Umm, no” Zane responded
“Good. Be here early tomorrow” She said, rather dismissively.
“What time?” Zane asked
“Very early” Suzie said. “Now get the fuck out before I beat your ass”.
That was enough warning for Zane to dress quickly and make his way home, commando.
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  #2  
Old 07-19-2017, 07:27 PM
teenslaveboy1 teenslaveboy1 is offline
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wow nice story makes me wanna start wearing panties loll
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  #3  
Old 11-08-2017, 08:03 PM
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danguy1955 danguy1955 is offline
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I'm moving to Chicago, and wearing a pink bra with one strap hanging out in every bar I can find.

Great story.
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  #4  
Old 11-09-2017, 12:14 PM
Demon Queen Demon Queen is offline
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Default Good Story But...

This may just be a personal preference but you users the f word far too many times. I otherwise like it.
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