Eric's Dreams Pt. 02

Yes, when Eric was undressed, he looked sort of like a chick.

Part of it was because he had a totally shaved body. From September to late May every year, there wasn't a hair on Eric's body. He shaved, meticulously, every two days...his underarms, his arms, his chest and stomach, his public area and his ass, and finally, his legs. He was as silky soft and smooth as any runway model. He would have shaved like that all year round, except he did enjoy going swimming, and he thought that being totally shaved would look too strange.

Another reason Eric looked like a girl -- his chest was feminine. He never understood why. But, but instead of wide, flat pectorals with two tiny nipples, peppered with chest hair like the men he often had sex with, Eric's chest was different. He had what looked like small breasts. Perhaps A-cup, when he was thin....but when he gained weight, it all seemed to go to his breasts. They would swell into B-cups and maybe a bit more than that when he gained a little weight. But whether he was thin or a little heavier, they looked just like a woman's breasts. When he crossed his arms just so, they popped up and out, and created a long deep line of cleavage in the middle.

Plus, his nipples were big. Nearly two inches across, when they were soft and puffy. When they got cold, sure, they tightened up. But when that happened their perimeter shrank, but their tips popped straight out, around three-quarters of an inch. Hard and pointy, and incredibly sensitive. One light touch and his cock would twitch, and start to grow. He always dreamed that if he did get a real boyfriend, his guy would pay lots of attention to those nipples.

But the trouble with dressing up as a woman was -- most gay men didn't like it. Several times, when the lights were low, drinks were on the table, and cocks were hard, he offered to bring out the lingerie and have a cross-dressing sex session. But every time, the gay man he had picked up had no interest in that whatsoever.

And this particular might, that presented a problem.

Eric was still reeling with passion from the session with the Camaro driver earlier in the week. It was so hot, and the driver came so hard in Eric's hungry ass, by all measures Eric should now be his bitch. As the urban myth goes, once a gay man lets another one cum in his ass, the bottom becomes the top's bitch. The idea thrilled Eric, and he wanted so badly to become the whore bitch of some hug stud. But alas, the Camaro driver didn't want to see Eric again. So there he was, a few days later, as the feeling of having an ass filled with cum slowly faded, and he was nobody's bitch. Damn.

He was a little pissed off that so many gay men didn't like his femme side. Sure, they liked the blowjobs Eric gave, and they liked to fuck him, but usually not in lingerie. They just wanted to fuck Eric's dazzling ass, and cum inside him, and then deny they were gay. Eric was so tired of the whole charade. So he decided this night would be different. This night, he would transform into a woman, and go get some straight cock.

He went to the mirror, and said "Eric...see you later." And with that, he began the two hour process of changing from a man, into a woman.

It was a long process, but he loved every minute of it. First, he put on soft music, always female vocals, featuring songs about falling in love. He removed all his male clothes, and pulled on a sheer cotton bra, and matching panties. He of course, took a moment to tweak his nipples....and he was so pleased and excited to see them poke through the fabric in such a sexy way. He poured a heavy glass of white wine, and sat down at his makeup table.

He started by pulling his long brown hair back, into a tight ponytail. Then he began the meticulous process of erasing his masculine features with heavy foundation, powder and concealer. Once that was done, all the signs he was male were gone. His face was now a blank canvas, waiting to become a masterpiece of femininity.

He began by applying dark contour, all around the edges of his face. Using a big, soft brush, he dusted the ears under his chin and forehead, below the ears and just a touch under his cheekbones. Done correctly, it gave his face a three-dimensional appearance, which was very attractive, and very kissable.

Next he turned to his eyes. They were the most intricate part of the transformation. He needed to use a light touch, because too little makeup would keep him on the male side of the net, while too much would make him look like a drag queen. He wanted to look like a pretty woman, not a Las Vegas showgirl.

He applied dark, smoky eye makeup on his eyelids, using his fingertips. He gently massaged it in, and followed up with heavy black eyeliner, flipping the edges of each eye into a flirty little curved point. Cateye, they called it. It was so feminine, he just loved that touch. He looked at his fine work as his palms massaged his hard nipples.

Next, the false eyelashes. He smiled as he remembered how difficult they were at first, with the glue and the clamps....but after a while he got the hang of it, and now it was easy. Shortly, he had long, lovely eyelashes, like a Hollywood starlet. He then applied mascara, blending the false eyelashes with his own. It looked lovely. He was almost done.

With a small, soft brush he applied while eye makeup to his eyelid, just under the arch of his brows. He blended it in again with his fingers, and looked at how that make his eyes just pop with drama. He finished by combing and lightly waxing his well-plucked brows, and make them a darker shade with a deep brown eyebrow pencil. Eyes were done, and they were killer good.

And finally - best of all - the lips. He drew around them with a deep burgundy lipstick pencil, going ever-so-slightly beyond the actual lips themselves, to make them look fuller. He then applied dark red lipstick, and finally, lip gloss, so they were shiny to the point of looking like they were dripping wet. And finally, he used an old trick many women knew....he touched the fullest parts of his lower and upper lips with white lip gloss....which made the lips look like they were catching reflections. Just what every man would be hoping for.

Genevieve was lucky, since at this point in the world, long hair on men was accepted. So he pulled his long brown hair out of its ponytail and brushed it until it was shiny and luxurious. The ordinary, straight brown hair, parted in the middle, became a playground of curls and bows and barrettes. The long brown hair fell down beyond her shoulders, and curled a bit at the end. She looked ever-so-cute.

And finally, the last step in his ritual. He looked into the mirror and softly said "Hello Genevieve."

She liked what he saw, and he couldn't deny it turned her on. There, looking back at her, was a tall, slender, drop-dead gorgeous -- girl. His femme persona, Genevieve O'Hara. The woman he so desperately knew he was, in his heart.

Time to dress.

Genevieve always wore two bras...both tight with big cups filled with socks. Years later she would smile, when she saw the tip on the internet. She had known all along, that to make your breasts look big and sexy, two bras were the key. The result was dazzling -- a heaving, deep cleavage, which looked not only like a real woman...but a totally stacked woman. She had to stop looking...or she would be forced to jack off, and then the passion would subside, and she would have done all this for nothing.

She liked it simple, in the belief it helped make her more passable as a woman. So, she put on black panties, black pantyhose, and a tight black under-bust corset, which cinched in her waist just the right way. Over that, she wore a tight navy blue polka dot dress, with a plunging neckline. It showed a lot of cleavage. She never could walk too well in heels, so she instead wore black, chunky clogs, which made her legs look good.

She put pearls in her pierced ears, and a string of pearls around her neck, and she was ready. It was show time. If she had done it right, soon she would be filled with straight, cock. And a lot of it.

She tossed her keys in her purse, and headed out for to Pookie's, the corner bar just between the gay and straight parts of the neighborhood. As she walked in, many, but not all of the people turned to look at her. That was good, she thought....just another girl. No one was staring, no one was elbowing their friends, saying look at the freak. She had done it. Genevieve was passing.

She took a seat at the bar, ordered a glass of the house white, and looked over the crowd. It was a good looking bunch, that was for sure. Mostly preppy young people, a good mix of guys and girls. Lots of college jocks and debutante types; the kind of people who would later brag to their suburban friends that they went to 'a bar in the city.' Living on the wild side, eh?

And here she was, a very horny crossdresser looking for straight cock. Looking to be somebody's whore bitch. She wondered which one of the men would cum inside her tonight.

It didn't take long to get the answer.

By the time she finished her first glass of wine, an impossibly handsome young man leaned against the bar next to her. Good clothes, good hair, good smile, good teeth.

"Hey. What's up?" he said. "Want something to drink?"

He was 21 or 22. Oh yes. A very good night lay ahead.

He bought her another glass of white, and he had a draft beer. They make some small talk, and she mostly listened as he told her about his job, his friends, his car. And by the time he asked her a few questions, she knew: he believed she was female.

She used her standard story -- that she was a secretary at a law firm downtown. Country girl, who just moved to the big city. Not many friends, and just wanting to have some fun after work. As she told him her story, she knew he wasn't even listening. He was looking at her so intently. Genevieve decided to let him have a really good look, so she opened her purse and bent down a little, allowing her cleavage to spill open. She didn't look up, as she spoke gently about making sure her keys were in her purse. It allowed him to look long and deep at her bountiful breasts.

She looked up, and he just stared. "Damn, you are so pretty,' he said. And within a few moments, she felt his hand on her thigh. It wasn't a grope, rather it was a light stroking with just a few fingers. Genevieve felt the butterflies explode inside her chest -- the guy clearly thought she was a girl. He didn't have any idea Genevieve was really Eric, with a long cock that was carefully tucked away, but one that had begun to stir when the jock stroked her thigh. She responded by placing her hand lightly on his thigh, and massaging gently. They looked at each other, and he smiled.

'Hey, uh, don't know if you got plans, but...'

'But what?'

'Well, I was thinkin' we could get out of here.'

'That could be arranged. You told me about your car. Can I see it?'

'Yep. Right around the corner.'

Genevieve smiled.

In five minutes they out the door and in his car. He leaned over and gave her a long, hard kiss, his tongue jamming into her mouth like a cock. She sucked on it, and circled it with her own tongue...giving him a hint about what was soon to come. He went right for her boobs, and started to massage them deeply. She moaned with pleasure -- his hard, big hands were pressing on her nipples, through the dress, and the two bras. Every time he pressed on them she felt shocks of excitement, which traveled down from her nipples to her cock and ass. She knew before long he would want to see them, to suck on her nipples -- and for that to happen she had to keep them looking fat and heavy. So Genevieve pulled down the top of the dress, exposing the bras.

'Oh yeah,' the jock said, 'You got incredible tits.'

He squeezed them hard again and again while they kissed. Then Genevieve reached down, and pulled down the front of each cup, reached in and pulled as much of her breasts out as possible...she didn't want him to see the socks, still tucked down in the bottom of each C-cup. By pulling them out she exposed her nipples, which, were now hard as a rock -- just what the jock was looking for.

His mouth latched on to a pink, hard nipple, and he groaned, as he sucked and licked and slurped. Then he moved on to the other one, sucking and licking. She wanted him to lightly bite them...she wanted to feel that sharp touch of pain...but she wasn't counting on it, since most straight men had no idea what to do with a woman's body.

Genevieve also knew that soon he would want to fuck. And he'd be expecting a wet, warm pussy -- which she obviously couldn't offer. So before that point, she needed to take the initiative.

As he sucked her nipples, Genevieve unzipped his pants -- and felt a nice hardness under the jeans. All she needed to do now was blow him, and let him come in her mouth -- while swatting his hand away from her ass, and the night would be perfect.

She unbuckled his belt, unbuttoned his jeans, reached in, and pulled out a hard, throbbing cock. Not huge, but perfectly good. About five inches long and thin, with a nice mushroom-shaped head. She squeezed it in her hand and started to stroke it up and down...waiting for his moan. It was right on cue.

Genevieve pushed him back against the seat, and lowered her head to do the job. He smelled sweaty and musky, and a little like pee, as she took him in her mouth. She didn't mind. All pick-up men smelled the same way. The only truly clean men, who smelled fresh and sweet as she sucked their cocks, were the ones who had walked right out of the shower and into her arms.

She rolled her tongue around his swelling cock, and pushed her mouth down as far as it would go. His dick barely hit the back of her mouth...so there was no deep throating to be had. She was a little disappointed, but forgot about it as she sucked harder, stroking the shaft with her hand, now wet with saliva. He head bobbed up and down, as he moaned, his eyes closed and mouth wide open.

'I want to fuck you,' he said, his eyes still closed.

Genevieve lifted her head, and stroked his cock with her hand.' I have my period.' And she sucked again.

'I don't care,' he said.

She lifted her head again. 'No, I can't do that. It's gross. And I have something up there.'

'Oh man...I want to fuck you so bad.'

'Well,' she sucked more, as a thought crossed her mind. She lifted her head. 'You could fuck my ass. I love that'

'Oh yesssss,' he said.

'But let me guide it in. I don't want you near my period.'

'OK. You're the boss.' He stretched his legs out, into the passenger side, as Genevieve turned around, her back to him. It was crucial that he not touch her, or see anything. She reached in between her legs and pulled her cock and balls up and forward. She pulled them above the elastic band of her panties, and they were out of the way. She then bunched up the fabric of her skirt over her package, making sure he couldn't see, and if he reached around, he'd find bunches of fabric instead of a cock and balls.

His cock was still rock hard and pulsing, and wet with saliva. Genevieve reached around and grabbed it with one hand, while pulling her panties aside with the other. She brought it to her ass, and rubbed its head against her hole.

"Gently now.' she said, 'don't hurt me.'

She lowered her hips, and the cock pressed against her hole -- hard. It was still outside of her as she lowered her hips more. It pressed so hard against her tight hole, and she thought she would need lube before it would go it. But, but she didn't have any, so she'd have to make do. She let it go, and spit into her palm. Then she reached back around and rubbed the spit on her hole, letting a finger pop inside, then two. Then she reached back and guided the cock to her hole once more. This time, as she lowered her hips, she felt it press -- press -- and pop! It slid right in. She sat all the way down on his lap, his cock pushing up inside her ass. Oh, the pleasure. It felt so good inside her. And he felt the same way.

'Oh jeez..that is AMAZING,' he moaned. She lifted her hips up, and sat back down...and he was buried to the hilt inside of her. Hot and hard and slippery. She reached around and flipped her skirt over, so there was nothing to see. She then guided his hands around, and onto her boobs. They were still popped out, above the bra.

"Pinch my nipples while you fuck me...please?' He was only too happy to oblige, unaware it was a ruse to keep his hands busy, and away from the bunches of fabric in front of Genevieve, which hid a hard cock and throbbing balls.

And now, she had done everything she could to keep her secret safe; now it was time to get fucked by a straight man.

She settled in to the rhythm...her hips rose and fell, up and down, forward and back. She kept a hand in front of her, guarding her own hard cock, in case he tried to reach around. She tried not to think about her cock, though, because she couldn't come...that would be a disaster.

He was bucking too, his hips thrusting, his cock plowing her warm, wet ass. She wanted him to come inside her. And she wanted him to cum fast -- in case he started thinking once again about fucking the pussy she didn't have. And Genevieve knew exactly how to make him come fast. She squeezed her ass as tight as could be around his wet cock.

'Ohhh.' He gasped. 'That feels incredible.' She squeezed even harder, and he began to buck wildly. A jackhammer of cock filling her ass. It felt so good. She suddenly felt pre-cum start to rise within her own hard cock. 'Oh no...' she thought...but the pleasure was just too intense.

Her ass was filled with cock, and its big mushroom head was hitting her deep inside, in all the right places, again and again and again. It was more pleasure than her body could contain. She knew she was going to come...she couldn't have stopped it if she tried. She felt the orgasm start to roll up in her balls, as she panted with lust.

The jock kept fucking her, unaware of the pleasure he was causing her to feel. And then, it was too much for Genevieve. The orgasm came fast and hard, as her cock erupted with come, spurting out again and again into the soft bunches of fabric that surrounded it. She never touched it...and yet the come spurted and shot, slowly becoming a soft stream, then a dribble.

'Oh no...' she thought. 'He's gonna know...he'll smell it. Oh no...'

But the jock was in another world as he fucked her hot ass. His eyes were rolled back in his head, and his hips kept thrusting and bucking, thrusting and bucking, feeling her tight, wet hole surrounding his throbbing cock. Finally he, too, couldn't contain the pleasure.

'Ohhhhhhhhhhh,' he cried, and Genevieve felt his back arch, his cock stiffen even harder, and as his whole body shuddered, she felt a hot spurt inside her, so hard it was like being hit by a fire hose wide open. His cock spurted again, and she felt that too. And again...shots of hot cum exploded against the walls of her ass.

'How much come does he have?' she thought...as two more powerful spurts slammed the inside of her ass.

That was it. He relaxed, and dropped back into the car seats. Now she had to make sure to keep her secret safe, for just a few more minutes. She slowly lifted her hips, and his cock popped out, slapping down on his belly. It was still hard, but starting to shrink, and certainly not the rock it was a few moments earlier.

Genevieve pulled forward, and knowing her ass was hidden by her skirt. She quickly pushed her come-covered cock and balls back into her panties, lifted her hips and sat down on the passenger seat. Glancing down, she saw her skirt was wet with come. Think fast, she thought.

'I came.' She said...smiling at the jock. 'I didn't think I could come if you were doing...that...but I did.' You are amazing.'