tagTranssexuals & CrossdressersAnal Sex with Stranger on a Train 05

Anal Sex with Stranger on a Train 05


Chapter 5

Peter finally meets Roberta again, the love of his life.

In just a few minutes, Robert returned to the room dressed as Roberta. Giving him a sexy cross dressing show, by her feminine antics and charms, she obviously enjoyed being watched by Peter. With a shake of her head and with a flourish, as if releasing her sword in Zorro, the gay blade, she released her long, blonde hair pinned to her head by a barrette. Her hair, as if a curtain on a Broadway stage fell down her back and behind her. In an instant, she transformed herself from a man, to looking like a nerdy, private secretary, and into revealing herself as a sexy bimbo.

Instead of covering and hiding her big breasts with an oversized sweatshirt, she wore a bra, makeup, and a long, flowing, low cut, colorful gown. Now she looked just as beautiful as she did on the commuter train. Even head on, while standing face to face, if he didn't know that Roberta was a man, he'd never guess that she wasn't a woman.

"Wow," said Peter. "That's some sexy transformation. How did you accomplish that in just a few minutes? I can't believe it's you, Robert."

"Roberta, if you please," she said with a flirtatious smile.

But for her big brassiere, he couldn't help but notice that Roberta wasn't wearing any underwear and his cock was already making a stiff appearance beneath his feminine gown, no doubt, in anticipation of having sex with Peter. Now as if Peter was a woman and Robert the man, he was uncomfortable seeing Robert's cock sticking straight out at him as if pointing to him and choosing him as that special someone. In the way she appeared before him as a woman, albeit a pre-op, transsexual woman, he wished she had a vagina instead of a cock.

"Is this better?" Roberta twirled around as if she was a dancer on Dancing with the Stars.

Feeling much more comfortable, albeit even after seeing the stiff impression of Robert's cock poking out his gown, Peter felt his cock stiffen by the mere fact that Robert looked so much like a feminine woman instead of a manly man. Easier for him to justify having gay sex when he fooled himself into thinking that he was having sex with a woman instead of a man, he felt better about having seemingly heterosexual sex with Roberta than he did in having gay sex with Robert.

"Yes," said Peter. "You really do make for a beautiful woman."

"How about from the back?" Roberta turned around, leaned forward, pulled her gown tighter around her, and wiggled her ass as she did on the train when grinding her firm, round buttocks into his cock. "How do I look now?"

Peter's cock involuntarily throbbed and pulsated when Roberta wiggled her ass like that.

"Not only are you a beautiful woman from the back but also from the front too. Don't tell my wife, that is, if you were to ever meet her, but you're much better looking than she is. I'm sad to say, now that I see you in the light, you look more feminine than my wife does too. Now that I think about it, comparing you to my wife, my wife is a little more masculine looking than you," said Peter laughing.

Never considering the thought before, now with him nearly out of his closed closet, he wondered if he had chosen a more masculine woman as a wife because he was more sexually attracted to males instead of females.

"Good to know, your comments are as complimentary as they are interesting and revealing," said Roberta. "It's gratifying for me to be appreciated when working so hard with all the subtle and not so subtle things that I do to look more like a woman than a man."

Peter stared at her as if staring at a real woman instead of staring at a cross dressing man.

"Now I can see how I could be so fooled into thinking that you were a woman," said Peter. "Even looking at you now while knowing full well that you're a man, I'd never believe that you're not a woman."

Suddenly, unable to control his lustful thoughts, in the way that she looked so beautiful now, he wished Roberta was his wife instead of the woman he married. Suppressing his homosexual thoughts before, he didn't bother to suppress them now. Easily, he could be gay for someone who looked like her? Only, what happens when she doesn't want to get all dolled up in her cross dressing outfits? What if she doesn't want to bother fixing her hair and putting on makeup?

Surely she doesn't go through the trouble of dressing like this all day, every day, like a woman instead of a man, does she? What happens when Robert wants to pile and pin his hair beneath his Chicago Cubs baseball cap, throw on jeans, a sweatshirt, and sneakers to go to Home Depot or to a ballgame and do what guys generally do on a weekend? When out and about with her and especially when with other men who aren't as enlightened about homosexuality and/or bisexuality, no doubt perhaps, suspecting that Robert was a cross dresser, he didn't know how he'd react to being out and seen in public with a transsexual. He couldn't possibly know how he'd confront that reality until he faced it.

"Thank you," said Roberta. "I'll take that as a compliment."

Realizing now how he was so fooled on the commuter train, he couldn't believe how much Robert looked like, talked like, walked like, and acted like a woman. She was so stunningly beautiful. She was so sexy. And she still had that incredible ass, the best as he's ever seen, touched, and felt on any woman.

"I love your hair," he said touching her long, blonde hair. "It looks so real. It feels real too," he said pulling out a handful of her golden strands before allowing them to magically fall back in place.

"That's because it is my hair. It's real hair," said Roberta putting her hair back in place with an experienced hand. "It's all my hair. I tuck it up and pin it beneath my baseball cap so that no one knows that I'm a trans woman."

"It is really? That's all your hair. No way," said Peter touching her hair again. "That's all your hair with no extensions? Wow!"

"Yes, it's all my hair and without extensions. I love my hair," she said. "The best part of me besides my blue eyes, big breasts, and shapely ass, I make for a much better woman than I ever did as a man. If I say so myself, I make for a much better looking woman than do most women," she said with a laugh.

"Trans woman?" Peter looked at Roberta with as much curiosity as he did with interest. "What's that?"

"For your information, just so you know who I am, I'm more than just a cross dresser. I'm more than just a transvestite. I'm transgender. I more associate with being female than I do with being male, I always have. My brain thinks I'm a woman and so don't I," she said. "My problem is in convincing everyone else to think the same way about me as I do about myself," she said with sadness.

"I see," said Peter.

Peter stared at her as if clearly seeing her for the first time. He liked the fact that she wasn't just a transvestite, so to speak, but a trans woman, a transgendered male who believes that she's a woman inside. It's the fact that she believes that she's a woman is the reason why she so fooled him, convinced him, and beguiled him into thinking that she is. More than just a man dressing like a woman as if in costume, she walks, she talks, and she acts like a woman. More natural for her to act female instead of masquerading as a male, her brain is encoded female rather than male.

If she looked this good now, he wondered what she'd be like and look like after taking more estrogen and after having the sex change operation. For him to fall in love with someone who looked like her, someone who really wasn't a woman yet, he wondered if he could put all of that aside and forget that she was born a man. He wondered if he'd be considered a gay man when being with a man who changed his sex from male to female.

With her already being a woman mentally and emotionally, he wondered if she'd want him after becoming a woman physically. Maybe wanting someone else, someone better looking, someone younger, someone taller, someone more understanding, and someone who wasn't already married, perhaps she'd be the one to reject him instead of him rejecting her. Suddenly he was jealous over someone else making her their woman.

"Yes it's all my hair," she said again and this time reaching around herself to run her hands through her hair that now rested on her shoulders and cascaded down and over her big breasts.

If there was really was such a person as Lady Godiva, imagining Roberta naked after her sex change operation, then that woman would be Roberta. She shook her head and tossed her hair again in the way that so many sexy women do when they have long, beautiful hair.

"Wow. That's so hot," said Peter. "I've always liked how women do that."

"Do what?"

"Toss their hair like that. That's so sexy," said Peter.

"Like this?" Roberta tossed her hair again.

"Yes, just like that. Boy, if you ever want to drive me crazy, do that when giving me a sexy look with those, big, baby blues," he said smiling as if he was smiling at a woman instead of a man. "Do that before giving me a blowjob," he said giving her a sexy look.

Moving her finger to her lip before taking it in her mouth to suck it, she returned his sexy look.

"Speaking of blowjobs, how about that blowjob now? Are you ready for me to suck you," said Roberta enticing him and teasing him by tossing her hair again while giving him a sexy look with her big, baby blues.

Suddenly Peter had this overwhelming urge to make love to Roberta as if she was a real woman instead of a cross dressing, transgendered man. Controlling the urge, in the way that he'd do with any woman who offered to suck his cock, Peter looked at Roberta as if he wanted to take her in his arms and kiss her while touching and feeling her everywhere. Unfortunately what held him back in showing his affection, his lustful, sexual desire, and his appreciation in receiving a blowjob from her was the fact that he knew beneath the clothes, the hair, and the makeup that she was a man masquerading as a woman. Even though he tried to understand her being transgendered, with black and white and man or woman getting in the way of his sexuality, he couldn't possibly even understand how she felt as a woman trapped in a man's body.

A rollercoaster ride of confused emotions and sexual excitement, going from how he felt as a heterosexual man with a beautiful woman to how he felt as a gay man with a cross dressing, transgendered male, to say the least, was confusing. Yet, it was enough that he was here now willing to have anal sex with Roberta again but, with all of this other stuff, having Roberta suck him and whatever else was on her sexual agenda for today was all uncharted ground in Peter's new journey into gay sex and homosexuality. Only going so far for right now, he wondered how far he'd go with the sexual dream that Roberta was a beautiful woman instead of a man. Being that she seemingly was more female than male when dressed as a woman or more male than female when dressed as a man, anal sex and perhaps a blowjob seemed to be the only thing he'd be willing to do with her. Even kissing her seemed out of the question.

He wished he had met her after her sex change operation. He wished he didn't know that she was a man who was a woman inside. Yet, then, he never would have confronted his true, sexual identity and sexual orientation had he met her after her sex change operation. Obviously for him to be here now in Robert's apartment, he was a gay man masquerading as a straight man as much as Robert was a gay man masquerading as a heterosexual woman. Two of a kind, with both of them masking their real identities, albeit with Robert being more honest and open in who he was than Peter admitting who he was, they were a good match for one another.

"Yes, I'd like for you to suck me," said Peter putting a gentle hand to the back of Roberta's blonde head as soon as she fell to her knees and took him in her mouth.

She started sucking him again. Only, unlike when Peter got an erection when Roberta stroked him on the train and when Robert stroked him earlier, oddly enough, he wasn't getting an erection now when Roberta was sucking him. With Peter now knowing full well that Roberta was a man, even though she looked like and acted so much like a woman, obviously having gay sex was making him uncomfortable. With the bigger picture in that he was coming to the realization that he was a gay man when he thought he was a heterosexual man all of this time, he was as tormented as he was confused. Unable to wrap his brain around it, he needed time to make the sexual delineation and to make the sexual adjustment in his mind.

"What's wrong?" Roberta looked up at him with his big, blue eyes and smiled while Peter looked down at Robert with confusion.

Knowing that Roberta was a man but with him looking so much like a woman was confusing him as much as it was sexually exciting him.

"Um, I don't know where to put my hands," said Peter while wishing that Robert had tits, big tits, in the way that he thought she had big tits on the commuter train instead of just a big, padded bra.

He couldn't remove the thoughts from his mind of Roberta being a man, even though he seemingly looked so much like a woman. He couldn't help but think of former Miss Venezuela, the newly crowned Miss Universe, Gabriela Isler, a transgender beauty queen being born a man but looking so much like a woman. Unable to continue the fantasy of Roberta, the fact remained that he was getting a blowjob from a man and not from a woman. Or being that Robert was all woman inside, just not physically on the outside, maybe he really was getting a blowjob from a woman and not from a man. Discombobulated and so thrown out of his comfort zone, was he a she or was she a he, he didn't know what to think or even how to react to his new found sexuality.

"Where do you normally put your hands when receiving a blowjob from a woman?"

Roberta gave him a look as if he was more trouble than he was fun and more of a problem than he was worth. Ignoring her look, Peter looked down at Roberta's big breasts while wondering if they were real or just a deception that were padded in a giant bra.

"I usually place my hands on her tits. I usually fondle her tits while fingering her nipples," said Peter hinting that he wished he could feel Roberta big breasts.

Enabling him to continue his fantasy, he wished she had breasts. Accustomed to feeling breasts in his hand and fingering nipples while he was receiving a blowjob, he didn't want to ruin his sexual fantasy by feeling a man's flat chest while playing with another man's puny nipples. Suddenly hearing the Village People singing YMCA, he didn't want to be with a man. He'd much rather be with a woman. Yet, if he was, indeed, a gay man, as Robert told him that he was, then by having sex with a transsexual, the best of both worlds, Peter was having his cake and eating it too.

"Knock yourself out," said Roberta rolling her eyes while removing her arms from her robe and allowing her robe to fall to her waist before unhooking and removing her bra.

"Wow! Holy shit you have tits," he said looking from Roberta's big breasts to look up at her face before staring down at her big breasts again. "I can't believe it. You have way better tits than my wife. You have spectacular breasts," he said. "I wish my wife had a breasts like your breasts," he said looking from her tits to look up at her. "Are you kidding me? Are they real?"

Peter stared at Roberta's breasts again as if seeing a woman's breasts for the first time.

"Real? It depends what you mean by real," said Roberta laughing. "In this age of computer technology, is anything real today? My breasts are as real as the breasts of many Hollywood celebrities. From Christina Aguilera to Nicole Ritchie to Fergie to Halley Berry to Heidi Montag to Tara Reid to Kaley Cuoco, they are the best breasts that money can buy," said Roberta.

"I see," said Peter. "So they're silicone, a plastic surgeons idea of what all women's breasts should look like. Correct?"

"Duh? What do you think? Of course they're silicone," laughed Roberta. "I'm a pre-op transgendered male and when I started developing breasts with the hormone injections they gave me, my hormonal breasts looked nothing like these," she said with as much attitude as he said with pride. "It took a plastic surgeon to give me what I wanted."

"Wow! You have better breasts than Jamie Curtis in Trading Places and Haley Berry in Swordfish," said Peter.

"With the money that I spent on the breast implants, I should have put that money to the sex change operation but I couldn't wait to have my own set of tits," she said cupping her breasts in her hands while smiling. "I love my big tits," she said. "Don't you?"

"Yes, I do. I love your big tits," said Peter. "May I?"

"Of course you may," she said sticking out her chest for the examination and hands on inspection of his horny hands. "Feel free to touch them, feel them, fondle them, and caress them. That's what they're for," said Roberta.

"Amazing. Your tits are just so amazing," said Peter moving his hands all over Roberta's big breasts. "Perfectly symmetrical, they are so round and so firm, yet so soft."

He looked at Roberta as if seeing her in a whole, new light.

"I hope to have the sex change operation done soon. I've already aced the psychiatric exam. My dream come true, I just need to come up with the money to transform myself from Robert to Roberta," said Roberta looking up at Peter before looking down at his cock. "Just as I can't wait to legally change my name, I can't wait to change my driver's license from male to female."

She took him in her hand again to fondle the head of his cock before stroking him. Then, as if she couldn't wait, she took Peter's cock in her mouth again. This time really sucking him, she stroked him faster while sucking him deeper. This time while fondling her breasts and fingering her nipples, Peter grew hard in Roberta's mouth, as hard as he's ever been when with any woman sucking him, even his wife, especially his wife.

"Wait," said Peter. With Roberta being a skilled cocksucker, Peter was getting too sexually aroused too fast from her blowjob. "Stop!"

When Roberta wouldn't stop sucking him, Peter pushed back on her forehead and stepped back to pull away from her mouth.

"What now?" Dropping her shoulders in rejected defeat, she sighed her frustration.

Rather than receiving a blowjob, he wanted anal sex. The reason why he was there was to have anal sex.

"My entire point of this little sexual experimentation into gaydom—"

"Gaydom?" She flashed him an angry look.

"Sorry if I offended you. I just didn't know what else to call your cross dressing, homosexual lifestyle," said Peter.

"My cross dressing homosexual lifestyle?" Not even an official couple yet, they were already having their first tiff. "You mean my soon to be heterosexual lifestyle and your present homosexual lifestyle," she said with a smirk. "If begging for a name, instead of calling this gaydom, you could just look in the mirror and call it what really is, Peter Land," said Roberta with a laugh. "If anything, with me believing that I'm more of a woman than a man, you're much more homosexual than I am," she said with a self-satisfied laugh.

"Peter Land. That's funny," said Peter. "That's really funny. Ha! Ha! So, I'm a gay man," he looked at her with an insightful realization. "Actually, you're right. With you born a woman trapped in a man's body, you're not homosexual at all. I get it. I do."

"I'm glad you're starting to understand," she said.

"Lemme get this straight. If anything, with me attracted to you, especially now that I know that you're a man, I'm the one who's gay, that is, unless it's the woman inside you that I'm attracted to and not the man. Right? I don't know. I'm so confused," he said.

Report Story

bySusanJillParker© 5 comments/ 35242 views/ 25 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: