Cross-Dressing Gay & Lesbian Sex 03

There are no underage characters in this story. All characters are over the age of 18-years-old.

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Emma's secret lesbian fantasy inspires Daniel to tell her his secret of being a cross dresser.

"Don't you have a sexual fantasy?" She looked at him with inquisitiveness while he looked at her with guilt.

'Do I have a sexual fantasy? I have a million of them,' he thought to himself. 'If only she knew how many sexual fantasies I have, she'd think me a pervert.'

Nonetheless all of the sexual fantasies he had, he didn't answer her.

"Surely, you must have a sexy secret that you haven't confessed to me?"

'If only she knew his cross dressing secret,' he thought to himself. Again, instead of saying anything, he remained quiet. 'If only she knew he'd like to have sex with a man one time just to see what it felt like to have a man suck him before, perhaps, he sucked a man, he wondered her reaction.'

Not wanting to play this silly game of him confessing his sexual fantasies to her and in this way, this was her show. She's the one who started their pillow talking conversation with I want to have sex with a woman. He didn't start the conversation with I'm a cross dresser. If he was the one confessing his secret, sexual fantasy instead of her, he'd volunteer all kinds of secret, sexy things. Only, instead, the spotlight was on her and not him.

She waited for him to answer her question and when he didn't respond with much more than a shrug, she continued.

"Surely, you must have some skeleton hidden in your closet that you haven't told me and would never want exposed for fear of the judgmental embarrassment that you're as normal as the rest of us," she said with a laugh.

He wished he had the courage to tell her all of his sexual fantasies. Maybe she'd have a good laugh over some of them. He loved her laugh. She was even so much more beautiful when she was smiling and laughing. Giving color to her cheeks whenever she was laughing, if he could have created the perfect women, he would have created Emma. Truly, he's a lucky man to have someone like her as his wife and his partner in life.

With her always teasing him and joking around with him, he loved her playfulness. He enjoyed the fact that they could talk about anything and share everything, that is, other than his cross dressing secret. Yet, he was hoping to rectify that soon by telling her that he enjoys wearing women's clothes. Only, now, with her confessing her sexual secret in wanting to have sex with a woman, he felt pressured to tell her his secret in wanting to wear woman's clothes and possibly even have sex with a man.

With such a negative stigma attached to cross dressing, as if he was doing something wrong by wearing women's clothes, he felt so guilty. Yet, something that most people who aren't cross dressers wouldn't understand, cross dressing was his badge of courage against his struggle with gender identification. Never winning the war but giving into the battle by choosing a side, male and/or female cross dressers straddle the line. Most times dressing as men, sometimes they give in to their always there and sometimes more emerging feminine side to dress themselves as a woman.

"We all have secrets," he said finally while feeling bad for not taking this opportunity to take her in his confidence and to tell her his deepest, darkest secret. "Being that it wasn't until I was 30-years-old when I met you and married you, I've done some things I'm not proud of doing but am not ready to discuss them with you just yet," he said deciding not to tell her that he's a cross dresser.

Assuring himself that he would tell her that he cross dresses, he'd tell her his cross dressing secret after she had her lesbian affair, if she was to have a lesbian affair and told him all of the sexy details during their pillow talk. This way with him having something over her, he wouldn't feel as bad in her having something over him. It wasn't that he didn't trust her to keep his secret, he was just filled with so much guilt and angst that he needed to cross dress that he feared she may not understand his need to dress as a woman. Usually always in control, he felt weak in his inability to control his wanton desire to cross dress. Feeling enough guilt that he felt bad about himself, he didn't want her feeling bad about him too. If only she knew he was thinking of having sex with a man, different than her wanting to have sex with a woman, when he didn't even understand why he'd want a man over her, he didn't think she'd understand that either.

Yet, with just her focused stare, as if she could see inside of him and knew what he was thinking, she looked at him as if she already knew or suspected his cross dressing secret. She looked at him as if she was a police officer waiting for him to confess and come clean with the truth. As if they were both thinking about one another's sexual fantasies, they fell silent until she spoke again. Only, with him not yet telling her his cross dressing secret and with her already telling him her lesbian secret, no doubt, now he had more secret, sexual fantasies to imagine and to confess than she did.

"Perhaps, you'd like to know what it feels like to be with another woman or with two women," she said treading on thin ice while prodding him to confess his sexual fantasies, whatever they were.

"Yes, that would be hot to see you with another woman naked and in bed together," he said.

Suddenly the imagined image of her with another woman took control of his mind. She covered herself by encouraging him with her look as if goading him to respond in kind. Exciting him in the way he excited her by fingering her nipples and fingering her pussy, sexually teasing him in the way that he was sexually teasing her, she slowly stroked his cock.

"Perhaps you'd like to watch me having sex with a woman," she said giving him a sexy look while exploring dangerous ground.

With her look making him want to confess his secret, he was so tempted to tell her that he was a cross dresser but not wanting to ruin the moment of her telling him about her secret, sexual, lesbian fantasy, his secret could wait. Obviously knowing her well enough to know what she wanted, if that's what it took for him to agree for her to have a lesbian affair, what she wanted was for him to confess that he'd love to have sex with another women too. At the very least, what she obviously wanted to hear was for him to agree for her to have lesbian sex with a woman while he watched. With him knowing her well enough that he could read her, obviously what she wanted was for him to tell her his sexual peccadilloes too, no doubt so that she wouldn't feel so exposed in his eyes. Perhaps sweetening the pot and as if this was already part of this prearranged deal, she conceded by giving him her blessings for him to watch her having lesbian sex with a woman and/or for him to have sex with her lesbian lover too.

'Wow! This lesbian affair must mean a lot to her for her to invite me to watch and/or to even participate to entice him to give her his blessings,' he thought.

Yet, somewhat troubled by her sexual lust for a woman, he wasn't sure how he felt about his wife sneaking around behind his back and lusting over women, even if only a sexual fantasy. No doubt when she was sexually thinking about a woman, she wasn't sexually thinking about him. Then, again, when he's dressed as a woman, he's not thinking about her either; he's only thinking about himself. Then, again, when he's dressed as a woman, he sometimes thinks of having sex with her while dressed as a woman. With the guilt he felt by not giving her as much oral orgasms as she gives him, he feared once she had a lesbian affair, she'd turn lesbian. He feared once she swung for the fences from the other side of the plate that she'd take off with Greta, Maureen, Ebony, or Janya. Unable to compete with a woman, he's just a cross dressing man.

Had it been a man she was lusting over instead of a woman, he'd be upset instead of being intrigued enough to be sexually excited. Curious to see how this would play out, imagined or real, he'd love to meet the woman who captured his wife's sexual interest. Sexually excited to see his wife naked with another naked woman, this arrangement could work out really well. Only, knowing Emma, this was nothing more than a fantasy and not much more than pillow talk. With him knowing her as well as he did, she'd never have lesbian sex. It's a good thing he didn't confess his cross dressing secret to her. Definitely, he should wait until she actually goes through with having sex with a woman, if ever she does, before taking her in his confidence about his need to wear women's clothes. Nevertheless, if her sexual fantasy never materialized into anything more than just pillow talk, the fact that they were discussing her secret, sexual fantasy of having a lesbian affair was hot.

"I'd like to see you having lesbian sex with a woman," he said finally showing her his cards by dipping his toes along with is cock in her lesbian, sexual fantasy.

He imagined her having sex with her beautiful, brunette, lesbian lover.

"Really?" She looked at him as if to see if he was teasing her. "You would?"

He imagine his wife French kissing her lesbian lover. He imagined her lesbian loving sliding down her body to eat her pussy. He imagined Emma having her tits felt and her nipples fingered while her brown haired, brown eyed woman licked her pussy.

"Yes. I would. That's kind of my sexually fantasy too, seeing my beautiful wife making love with another beautiful woman," he said with a dirty laugh. "Actually, that's a lot of guys' sexual fantasy to watch their wives or girlfriends having sex with another woman."

"It is?"

"Oh, yeah, big time," he said encouraging her with a nod of his head.

Exhaling a big sigh of relief, she hugged him and kissed on the lips.

"Thank you for being such an understanding husband," she said. "Oh, my God, just the thought that I have your blessing to have lesbian sex makes it all the more possible without having any of the guilt of the lying and sneaking around," she said staring at him while awaiting his answer. "And would you want to participate too or just watch?"

Lying and sneaking around? He wondered what she meant by that. Has she been lying to him and sneaking around behind his back or did she just make a comment without thinking of what she was saying? With him now suspicious of her presently having a lesbian affair, she made it sound as if she was already having a secret, lesbian affair. With her describing her fantasy lover in such detail, she made it sound as if she already had a lesbian lover. Suddenly, he felt as if there as an interloper in his marriage. Suddenly, he felt that he wasn't the center of her sexual attention in the way that he's always been.

"Being that this would be your first time with a woman, if you don't mind, I'd rather just watch." He said as if Emma was really going through with having sex with a woman. "Maybe, if this goes well, the three of us could get together another time," he said talking as if she already had a woman in mind and this experimental foray into lesbianism was really going to happen. "Or maybe with this being your first time with a woman, you'd rather be with her alone."

If it was to ever happened, he wondered how he'd really feel about her having a lesbian lover. Just looking at the upside, he didn't even think about the downside until now. Would he really want a third person in his marriage, in his bed, and involved in his personal affairs? Would he trust another person with all of their secrets and personal things? Would he want someone snooping around his bedroom, his bathroom, and his computer when she was with Emma and he wasn't at home?

Why on Earth would he want to share the attention of Emma with anyone, even with a woman? Yet, if she had a sister, she'd be talking to her all the time on the phone and telling her personal things that he may not want her to tell anyone, especially her imagined sister. Much like some of her close friends, she still honors the boundaries of what she says and doesn't say about him and/or their marriage. Only, the boundaries of what she confesses to her lesbian lover may be wider and more forgiving than the boundaries of what she says to her close friends and/or even to her sister, if she had a sister.

"Actually, I'd like for you to watch first before having a threesome," she said. "Just as you'd like to watch me having sex with a woman, I'd like to watch you having sex with another woman too."

What? Seriously? She'd like to watch me having sex with another woman? Was she just saying that as his tempting reward for allowing her to have sex with a woman or did she really mean that she'd like to watch him having sex with another woman? He couldn't imagine any woman, unless she was a swinger, wanting to watch her husband having sex with another woman. A new, sexy dimension to their relationship, he looked at her shocked by all that she was confessing. Wow!

Her confession added to the guilt he felt over him not confessing his cross dressing secret to her. Especially now that she was talking so very much about her imagined lesbian lover, he needed to come clean. He needed to tell her that he not only enjoys wearing women's clothes but also that sometimes he thinks about having sex with a man. If she was so willingly able to confess all of what she's already confessed to him, he should do the same in confessing his cross dressing secret to her. Nonetheless his not confessing his secret to her yet, he liked the idea of watching her having sex with a woman as much if not more as he liked the idea of her watching him having sex with a woman. If it was ever to come to pass, he just wasn't keen on the idea of watching her with another man, if indeed that was her next secret, sexual fantasy and her next transgression.

"I don't think I could watch you having sex with another man," he said making a sour face while putting that out there for her to know his displeasure with that.

With him saying that about not wanting to watch her having sex with another man, she fell silent as if she was debating about saying any more. Was that on her agenda to not only have sex with a woman but also with a man? Was that her next sexual fantasy that she was about to confess? Was it just a guy thing that she could watch him having sex with another woman but he couldn't bear to watch her having sex with another man? Or was she just agreeing that he could have sex with her lesbian lover just so that she could have guiltless sex with her lesbian lover. Wow! They haven't even embarked on this lesbian, extramarital affair and it's already causing problems between them. Then, she floored him with what she said next.

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"She has a husband," she said.

Bingo! That explains why she suddenly fell silent when he said that he couldn't watch her having sex with another man.

"She has a husband?" Nearly ruining his sexual fantasy of her with her lesbian lover and with him in a threesome with her and her lesbian lover, he looked at her stunned. "Who has a husband?"

"My, um, fantasy, lesbian lover," she said.

Now not knowing if her fantasy lover was real or imagined before, he suspected she was real now. Not wanting her to clam up, threading carefully, he persevered in his questioning of her to uncover what was true and what was fiction. Confused, he wasn't sure if this was a sexual fantasy of if Emma has already had lesbian sex. Chances are if this woman was real, then maybe they've already had lesbian sex.

"She does?"

"Yes," she looked at him with guilt written all over her face.

"And what's his name?"

Not yet even knowing the name of her imagined lesbian lover and if her lesbian lover and her husband were even imagined or real.

"Martin. His name is Martin," she said.

Just as he was curious what her lesbian lover looked like before she described her to him, now he wondered what the husband of her lesbian lover looked like. What kind of man is he to allow his wife to have a lesbian affair? Maybe he's a man just like him? Maybe it sexually excites him to watch two women having sex with one another in the way that it would surely sexually excite him to watch his wife having sex with a woman.

In that moment, he knew she had been unfaithful to him just as he had been not honest with her in hiding his cross dressing secret from her for ten, long years. Playing her game now, but careful not to spoil the sexy fun, he persevered in his pillow talk. Not wanting her to hold back or to lie to him, he needed to know more. He needed to know everything. He needed Emma to tell him if she's already had lesbian sex or not.

"And is the husband of your fantasy lover okay with his wife having sex with women or is that something he doesn't know," he said with a nervous laugh. "Or maybe he wants to watch too."

She paused to look at him as if to read him before saying what she said next.

"With them having an open marriage, he knows that his wife is bi-sexual. Actually, he likes to watch too. He enjoys watching her with other woman," she said pausing, "and with other men. Should we get together, he'd like to watch too," she said pausing again as if debating if she should say what she was thinking.

Confused, he still didn't know if she was talking about a real person or an imagined one. Only, now her fantasy characters sounded more real than imagined. In the way she described the woman of her sexual fantasy, he could already see her in the way that he was unable to see Greta, Maureen, Ebony, and Janya. Suddenly, with her bags packed, he imagined her waving goodbye to him when leaving him for her lesbian lover and her husband.

"You mean, for you to live out your sexual fantasy by making love to another woman," he said already knowing the answer to his question. "I'd have to agree to another man seeing you naked while the both of us watched you and his wife having lesbian sex?"

He wondered how he'd react to another man seeing Emma naked. He wondered how he'd react to seeing his wife naked with another woman. In the way that he wanted to and was invited to have sex with her lesbian lover, he wondered how he'd react to her lesbian lover's husband having sex with his wife. He wondered how his wife would react to another man having sex with her and making love to her before fucking her. If it wasn't enough that her sexual fantasy was having sex with a woman, going from that to them having a threesome, now they were talking about swapping partners.

"I guess so. Yes," she said seemingly uncomfortable with his reaction to another man seeing her naked. "I really didn't think it through that far being that I wanted to run it all by you first."

Run it all by me first? Run what by me? He still didn't know if their pillow talk conversation was imagined or real. Now he didn't know if she was still only talking about having sex with just a woman or if having sex with her husband was part of the deal. Maybe now that he knows her lesbian friend has a husband who wants to watch his wife with her too, suspecting that Emma would want to have sex with him too, she was worried that he'd squash this lesbian tryst before it even started. Maybe these people really do exist and are not just fantasy characters in her head.

"So, being that you already know she has a husband and even know his name, it sounds like you already have someone in mind," he said with a nervous, little laugh while prying her for more information.

He looked at her with curiosity while she paused in her pillow talking dialogue to look at him as if already apologizing for being unfaithful to him.

"Actually, I do," she said avoiding making eye contact with him. "She's an acquaintance. One of my father's clients that he had when she was having to deal her mother's estate after her death," she said.