Jasmine and Doug lay there, sated for the moment. Jasmine thought about Doug and all their communication before this meeting. They’d gone over several fantasies of his, planning several. There was one she was thinking about; she wasn’t sure he would go for it but thought there was a pretty good possibility. She turned on her stomach and put one arm across Doug as she lifted her head, looking at him closely.
“Doug, what do you have planned for the rest of the day?”
He wasn’t sure where she was going with the question, but he also knew they were well beyond any expectation he had when arranging to meet a transsexual escort. “Nothing really, just see some of Chicago and go to the football game tomorrow. It’s a 1 PM game, so I’ll be heading home after that.”
“I have something I would like to do. Would you come to my place and let me dress you?” Jasmine wanted to rush through an explanation but knew too much information now might scare him off. She really wanted to do this, not just for him but for her as well.
“What do you mean?” Doug looked a little confused.
“You are not too tall, slender without massive shoulders. I want to make you up.”
“As a woman?”
She smiled, “Of course, you already look like a guy.”
“Jasmine, I don’t think that’s a good idea.”
She pushed herself up and sat cross-legged on the bed. “I’m not talking make you a transsexual. I just want to see if I can make you a passable woman.”
“Passable?”
“I think I can make you more than just passable, as in someone seeing you would not even realize you are a guy in women’s clothing.”
“A dress?”
Jasmine laughed. “No, not in the winter. I think long sleeves and pants would do fine. Just an experiment and maybe a little fun.” She was happy he didn’t immediately go all macho on her. He might not be thinking it possible, but she had one more ace to play. “I’ll even sweeten the deal. I will wager the envelope you gave me that I can make you more than passable, that I can turn you into a beautiful woman.”
Doug knew just how much money she would be giving up, and it was considerable. As he thought about it, he didn’t realize how transparent his face was to her. She knew he was thinking it was a sure thing because there was no way she could turn him into a woman. Plus, a bet is a bet! “Who would decide?”
“You would. Let me do all the work, just no peeking until I am done, and you decide!”
Doug was thinking how nice it would be to have that escort fee back. He also had another envelope prepared as a ‘tip’ that he was perfectly willing to give her since she had already rocked his world several times over. “I’ll be the judge?”
“Yup, I just want a blank canvas. Nothing crazy, no eyebrow tweezing, just make-up, clothes, flats instead of heels, and maybe a little undergarment help. Then I will unveil you in front of the mirror and you decide. My word on it!”
Doug thought and basically decided, ‘What the hell!’
She saw him make up his mind and thought again how lucky she was and how much fun this was going to be, even if Doug didn’t know the half of it.
Other than the clothes on his back and his shaving kit, they headed for her place.
. . .
Four long hours later, Doug stood in front of a full-length mirror, surprisingly nervous. He had followed every instruction and let Jasmine do anything she wanted. The underwear felt weird; the bra with its inserts felt even weirder. She glued them to his chest so they would look ‘normal’, in her words. She swore they would come off with a little solvent made for the glue. She even showed him the bottle to prove that she had it when he demurred at first.
Some of it was fun; they kept teasing each other, touching, kissing. Having Jasmine’s undivided attention was actually a blast.
The wig was heavy on his head, a red wig, which she said went well with his skin and eye color. There was a sheet over the mirror and now was the moment of truth and he figured he would win the bet, there was no fucking way . . .
Jasmine quickly yanked off the sheet and suddenly Doug was face to face with the result and he froze in shock. Jasmine grinned at his surprise. She knew he didn’t think she could do it.
He thought he was looking at a picture until he lifted his arm to his face and the image in the mirror moved. He couldn’t help himself, “Holy fuck!” He stared at the mirror and the only negative thing was the look on his face, or was it her face?
The wig was styled in a carefree look, not quite windblown, but it looked so natural. The face was the real central point, he had shaved very close, and even though he knew how much make-up she had used on his face, it didn’t look it. It looked smooth and the wings of mascara looked … perfect. He’s seen pictures in magazines that didn’t look this good.
She dressed him in a peach-colored tubular sleeveless top which seemed to emphasize the breasts. Over it was a contrasting light green jacket that was open. A pair of dark-striped pants made it look like he had hips; the stripes weren’t straight, but almost like an optical illusion. She did tell him no heels because it might take too long to move well in them, so she put him in a pair of peach flats that were actually a little tight, which made him walk with more care than usual. Some jewelry and some glittering gemstone glued near the corner of his eyes completed the look. He looked… the words wouldn’t come.
“So, from your reaction, I think I just won our bet?”
Doug couldn’t say anything; he couldn’t stop looking at the mirror. The girl looking back was stunning.
Jasmine loved his reaction, but before he lost the high he was on from just looking at himself… no, herself, it was time for phase two.
“Okay, Doug. While I am getting ready, you need to think of a new name. I am not calling a knockout like you, Doug.”
Doug still couldn’t take his eyes off the mirror, and said “Ready for what?”
Jasmine peered around her closet door for a moment. “If you think we are going to sit at home, you are crazy. We are going out!” She saw the nerves set in right away and it cause Doug to look away from himself. “Don’t worry, I know a nice place we will fit in fine. No pressure, no hassles. You look amazing and no one will bother you, especially with me next to you. Don’t sweat it!”
While Jasmine was changing, Doug was getting nervous just thinking about it. He looked at himself again and was torn more than he thought he would be. Part of him said, “Absolutely no fucking way!” But there was a tiny part inside where he was curious if he could pull it off and pass as a girl.
Jasmine came out and Doug was stunned all over again. She picked an outfit practically the opposite of his, a tight peach dress that showed off her skin tone, with a belt the color of the light green jacket he was wearing. Her gorgeous legs were on display and as she sat down to do her make-up, Doug felt himself stirring.
Jasmine felt his eyes on her. “None of that until later. Let’s just go have a little fun, a few drinks, and maybe a dance or two. I want to show off my new girlfriend!”
While she got ready, Doug sat and then paced around the room. His look was so different, but also just the feeling of the clothing was so different. He wasn’t sure why he was wearing pantyhose under his pants, but it really felt both strange and sexy. The softness, smoothness, and firm hold were very different. Just walking across the room felt very, very different.
She was ready quickly, and she just kept the two of them moving like going out was a forgone conclusion rather than a question. She never gave him a chance to get stubborn. Almost without him realizing it, they were in her car.
“Since you haven’t given me a name, how about ‘Dani’? It’s sexy and since it starts with a ‘D’ it will be easier to get used to it.”
Doug didn’t say anything as he ran the name ‘Dani’ around in his head.
It didn’t take long before they pulled around a club. Jasmine parked on the side and led ‘Dani’ around the corner. There was a small line, but Jasmine went past it and hugged the bouncer controlling the lines. The bouncer looked unlike any bouncer Doug had seen and was probably the most muscular woman he had ever seen. They were let in and they took a table off the one side and ordered drinks.
Jasmine gave Dani a little time to settle down and while a few people stopped off to say hi and get an introduction, no one freaked out and it seemed to calm Doug even more. No one was pointing any fingers and while he could see some of the women were not actually women, the club seemed to be more of an unthreatening place than anything else. Several of the people were what Doug would have said was not passable, but they were being treated… well, he would have used the word ‘normally’. Doug was shifting mental gears as he realized the very concept of ‘normal’ was going through some re-defining in his own head. He sipping a drink, a fruity thing with a skewer of fruit and a damn umbrella that he wouldn’t have ordered for himself in this lifetime, but it seemed to fit both the atmosphere and everyone he saw was drinking something similar. He really wanted two fingers of scotch to settle his internal constipation, but this drink was stronger than it looked and it even tasted pretty good.
Jasmine didn’t push anything, just allowed the world to go around the two of them. A couple of people wanted to join them, but Jasmine waved them off. She didn’t think Dani noticed, but she didn’t want anything to make him nervous again. After a time, Dani leaned close and asked where the restrooms were. She whispered where they were and behind his back, she gave a high sign to one friend, who then preceded Dani to the loo – partly for protection and party for other reasons.
Jasmine smiled as Dani walked away, he wasn’t quite as smooth as some, but he was relaxed enough to move better and better. She waited a few minutes and followed him.
After Doug did his thing in a bathroom cubby, which was also different because of the layering he wasn’t fully used to. He exited and saw a woman standing in front of the large mirror adjusting her make-up.
“Hi!” the woman said to Dani.
“Hi!” Doug washed his hands and paused longer to look at himself again. He still couldn’t believe the transformation.
“Hey, can you give a girl a hand?” The woman at the sink was smiling at Doug in the mirror. She was tall and slim, with black hair and a nice smile. She was in a skirt and blouse, buttoned high on her chest.
“Uh, sure, I guess.”
“Come over here.”
Doug stepped closer. The woman grabbed Doug’s hands with a very strong grip and shoved his hand under her skirt. Between one second and the next, Doug was holding only the third penis he had ever touched. He went to jerk away, but the woman’s grip was strong.
“It’s okay; just play with it a little, like you would your own. I can’t go back out there with my skirt tenting! It’s not a big deal, just stand behind me and treat it like you would your own.”
Dani paused, unsure of what to do.
“I’m, Andrea and I think you look incredible. If you weren’t with Jasmine, I would truly assume you were a GG.”
“GG?”
“A genetic, or genuine, girl. She’s amazing, isn’t she?”
“I guess you two are friends?”
“Oh yes, we both come here because it’s a great place without the pressure we feel in regular clubs. It’s nice to be in such a place.”
During their brief conversation, Dani’s hand never left her, and he felt her harden nicely. Then she pushed back against him, and he felt himself responding as her ass rubbed him.
“See, I told you it’s no big deal. I just have trouble getting myself off. You are really helping me out, and I feel you might be enjoying it a little yourself.”
Dani looked in the bathroom mirror and saw two women looking back. Andrea’s skirt was flowing enough that it looked more like he was rubbing a pussy than stroking a cock.
“A little tighter; you aren’t going to hurt me.”
When he did so, she responded with almost a mew of pleasure. She would push back in time with his slow strokes; it almost felt like they were fucking. Then he felt a presence behind him.
“I was wondering what was taking you so long; I see you met Andrea?”
Dani jumped at the sound of Jasmine’s quiet voice over his shoulder. He would have moved, but she pressed against him from behind and her arms held him in place. “Don’t stop, Dani. Andi’s a bit of a slut, but she’s got a great cock.”
He felt Andrea moving as she pulled her skirt off and tossed it on the counter. He looked in the mirror and saw his hand around her cock. She wasn’t circumcised and he could see the collar of skin covering and uncovering the head. It was a view he found surprisingly sexy. Feeling Jasmine pushing against his ass helped that feeling. He found himself reacting more than thinking. Andrea’s ass wasn’t hurting either.
In a moment, everything changed. Andrea pulled away from him and sat upon the counter. She started stroking her own cock and Dani found she couldn’t look away. There was a little moisture making the tip shine in the bright bathroom lighting.
Jasmine pushed Dani just a little. “Go ahead, baby!”
With that little urging, Dani bent at the waist and found herself inches away. If she thought about it, he might have walked away, but she didn’t want to. But his mind was awhirl with the feelings and sensations of last night and today with Jasmine, but her mind was more tightly focused on what was in front of her. He might have been able to say no, but she couldn’t not take Andrea in her mouth. She felt different from Jasmine, wider and her foreskin brushed her lips as he sucked hungrily.
The dichotomy was a little confusing, but at that moment, he went from Doug, a guy in girl’s clothing, to Dani, a woman in her own right. She felt sexy and strangely empowered by all that was happening. If he paused to think, nothing might make any sense, but something was going on within him that made all this easier to accept.
Dani felt Jasmine doing something behind her, but she wasn’t paying that much attention. Andrea’s cock had her total concentration. It was a very different feeling than Jasmine’s, not that she felt she was an expert. Andrea was about the same length but thicker. Her scent was sharper, more earthy. As she concentrated on what she was doing, she felt something touch her right hand. Instinctively, her hand grasped, and she found herself holding another cock. For a moment, she assumed it was Jasmine’s, but she still felt her pressing against her. Before she could do anything, another cock touched her left hand.
It felt so strange, trying to coordinate the actions of both hands and her mouth at the same time. She felt her pants falling and her hose tugged down, and then panties were pulled to one side. As Jasmine rubbed the now-familiar lube on her bumhole, she leaned in and whispered to her, “Dani love, you might remember one of your fantasies was to be part of a transsexual girl orgy? I do so hope this meets your expectations?”
As she said that, she felt her push into her ass. Her mind was totally overwhelmed with so many sensations she was not capable of processing. One last surprise was when a mouth engulfed her own hard cock. Somewhere buried deep within her, she thought about what was happening. Five other people were using her and she was loving it!
She slowly got into a rhythm, her hands working up and down in time with her mouth sucking Andrea. She felt Jasmine pushing into her at the same time, pushing her cock into the warm mouth below. Her mind might be stretched to the limit, but her body was learning quickly. It didn’t take long when she exploded into the mouth of whoever was below her. She didn’t have a chance to catch a breath as Andrea pushed deep into her mouth and started fucking her face. It might have been uncomfortable if she thought about it, but it wasn’t for long before she felt her cumming and filling her mouth much more quickly than Jasmine had and some flowed down her chin. Below her, the woman who had sucked her so wonderfully started licking her chin and neck as Andrea overflowed her ability to swallow.
The two cocks left her hands and she grasped the edge of the counter to stay upright. She had one hand on each side of Andrea as Jasmine started really fucking her. She looked to the left and saw one of the women who had stopped by to say hello to Jasmine standing there holding her own cock, stroking it slowly. To the right, she saw the woman who had been with her doing to same. Andrea slipped off the counter and kissed Dani hard. As she did so, she moved off to the side and was replaced by the other two women. They were holding their cock close to each other and offered them both to her mouth at the same time.
Dani could barely hold both of them for long, but she did his best; each time Jasmine thrust into her, she lost contact with those two. She felt her speed up, and she knew Jasmine was close to her own wonderful orgasm. She tried to suck on the two cocks in front of her harder, but it was impossible as Jasmine pounded her harder and harder. They moved off and she used her arms to hold herself as she got fucked. There was no other word for it, she slammed into her harder and harder until he felt it, she pushed deep and froze and the feeling of her cum filled her.
She couldn’t bring herself to move as she felt Jasmine pull out. Someone cleaned her up a bit and even pulled her clothing back into some semblance of order. When she finally stood up straight, there was a small smattering of applause as the five women looked at her. Each stepped up and kissed Dani gently before leaving. Andrea came back to the table with them.
Dani still couldn’t talk; she couldn’t find the words. Somewhere deep inside, Doug was still there, just quiet for the moment. She took a sip of a fresh drink; the fruity concoction was the perfect thing for her parched throat. Andrea leaned close to him on one side, Jasmine on the other. At Jasmine’s request, one of the servers took their picture. Andrea said nothing; Jasmine waited for Dani to recover. She knew she had taken a big risk but hoped Doug/Dani appreciated it. Dani put her arms around both ladies and hugged them to her.
“You know, Jasmine, that orgy idea was just a passing thought. I didn’t realize I would be at the center of it?”
Jasmine put her head on Dani’s shoulder, “I know, but it seemed like a good idea at the time. Are you going to tell me you hated it?”
“Who were they?”
“Good friends of mine, like Andi here. She’s a bit of a slut, but what can you do?” Andi reached over Dani and smacked her lightly.
“Sure, I’m a slut! Who just fucked her girlfriend in the loo of this club?”
Dani paused and the more practical Doug showed a little, “How come we didn’t get caught? No one came in, or was I that oblivious?”
Jasmine grinned, “Well, once you wrapped your lips around Andi’s cock, you were pretty tightly focused. But I cheated and had Louisa, the bouncer, direct everyone away for a while. She told them it was closed for cleaning. I doubt we fooled anyone, but appearances do count.”
Andi laughed, “Jas, it does mean you owe her a favor!”
Jasmine grinned, “I know and it’ll be fun!” She looked at Dani, “Too bad you won’t be here next week. Louisa’s next night off is Wed. She loved a lot of attention!”
“Louisa, the bouncer who let us in? The muscular one?” Dani asked, mildly curious.
Jasmine smiled, “Yes, she’s into bodybuilding and her body is a wonderful exploration of hardness and softness. She’s another old friend. You would enjoy every inch of her.”
Dani actually blushed at the thought. He glanced over and Louisa looked at them. Doug would have found her a bit too much of a masculine woman, but Dani thought she looked sexy and very powerful!
Andi came back to Dani’s hotel with them after a quick stop at Jasmine’s to pick up a few things. Dani thought about changing but decided tomorrow was soon enough. The three of them made love several times until the early hours. In the morning, after some quick cleaning up, Andi sat there in bed and watched Dani go back to being Doug. She shook her head slowly, “You are a striking person in either persona.”
Jasmine stood there, slowly stroking herself. Her friend was sitting on the bed holding her own, now very soft cock. They both looked at Doug as Jasmine said, “Do you really think you can go back to your vanilla sex life now?”
Doug looked back at them, his face thoughtful, then his eyes dropped to Jasmine’s slowly hardening cock.
The three of them knew the answer, or was it the four of them as Dani looked out from Doug’s eyes in hunger.
