Bob and the Lawyer

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Bob's first experience as a woman.
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Bowzer
Bowzer
45 Followers

(This is the third short story in a series. The first was Bob and Bigfoot, and the second was Bob and the Wife.)

"Oh, my," said Diane. Her pink tongue caressed her red lips, she felt her heart fluttering, and, truth of truths, she felt a little wet down below.

She had always wanted a woman, but had never had the courage.

Often she had dreamed about Barbara, but Barbara was not approachable.

Bob, however, was.

Bob was a man, men had their brains in their manhood, Bob could be approached. It was a simple logic.

Of course, Bob, being a man, didn't necessarily make Diane wet.

Bob being a woman, however, did.

Well, maybe not a real woman.

But woman enough to set off Diane's estrogen drip.

She stared at the voluptuous figure and was in awe. Bob had managed to establish the proper proportions. Her..His...He had selected the right shade of lipstick to make the lips fuller without being garish. He had even managed to apply shade and mascara and avoid the tart look that most men trying to be women fell into.

She was breathing so hard that her breasts felt constricted.

And she knew she had to get some of Bob.

"I need a drink," said Barbara.

Barbara went to the wet bar and reached for the bottle of Vodka in the silver stand up rack. With trembling hands, careful not to so much as brush against her husband, or even look at him, she splashed a stiff shot into a tumbler.

Tumbler up. "Ah!" Tumbler down. Her lipstick was smeared on the lip of the glass, She smacked her lips and poured from the bottle again.

"You look...divine, Bob." Diane was glad to find that her voice still worked, though it was a little breathy and hoarse.

"Thank you, Diane." He had pitched his voice higher than normal, and it was obvious that he was trying to figure out how to speak like a woman. "Are those your real nipples?"

Diane looked down at the rise of her breasts. She wasn't wearing a bra under her creamy, boy beater tank top, and her little erections were struggling against the soft material. She looked up at Bob, felt a fluttering contraction between her legs, and said, "Oh, my."

Barbara had turned away from them and was tilting another tumbler. Hard, biting liquid cascaded down her throat, but it felt soothing to her. She shook her head, shivered, and escorted the bottle over to a brown couch. She sat heavily, splaying her legs, and poured another drink.

"So, Bob," Diane swallowed to wet her throat and licked her lips, it felt like all the moisture in her body had decided to go to her pussy, "What's happening?"

Statuesque in figure, keeping his face just so, he was not quite sure what the effects of talking would be on his make up, Bob said, "Oh, not much."

Not much, Diane thought. He stands before me in full drag and says, not much.

"Well, uh, I notice that you've changed your wardrobe just a wee bit."

Bob held his arms out in a very graceful motion and looked at his body, "This?" Then the boy of him peeked through, "Do I look all right?"

It was all Diane could do to stop herself from tackling him and ravaging his body. "I think you've done just fine." She raised a hand and caressed his jaw. The hand trembled.

Bob stared at her hand, took it in his own and examined it. "I love your nails."

Her nails were a glossy, dark red. Bob's were pale and stubby.

"We could do your nails."

"Could we?"

They faced each other, Diane trembling at the thought of him, him trembling at the thought of manipulating those hands, making them feminine, giving them a real set of nails.

On the couch, Barbara slouched back and raised the bottle directly to her lips. She was definitely getting light-headed, but what did it matter? Her husband, her staunch, check-writing,, Republican husband, had turned into a woman, a better looking woman than herself, it appeared, and her best friend looked like she was getting ready to rip off his clothes and mount his bone. And she, dammit all, didn't care. After all, she had a new best friend. She hiccuped as she raised her best friend yet again.

At the wet bar, Diane said, "And perhaps, while we do your nails, we could talk a little bit."

"About what?" asked Bob. She hadn't really wanted to talk to him before. In fact, she had always displayed a kind of disdain for him.

"Oh, I don't know. Fixing cars, baseball scores, why you're a woman. Things like that."

For the next half hour, while Bob told Diane the story of the Sasquatch, Diane worked over his nails. She put on new nails, painted them a most delicious red color, and then coated them with lacquer. When she was done, he held them up and stared at them in awe.

"These are just the most beautiful, the most scrumptious things I've ever seen. His voice was getting softer and breathier. Diane realized that he was mimicking her, learning from her as they went along. His progress was nothing short of astounding.

"And you say that the Sasquatch, what it did to you, is responsible for your...change of attitudes."

He lowered his hands and looked into her face, which was very close. Her eyes were half shut and her mouth was moist and red and slightly parted.

"Do you believe me?"

"Oh, certainly, I believe you," though she didn't, and, personally, felt that he was looney tunes and so the fuck what their faces were getting closer and she was licking her lips and her hair was tousled and very sexy and she felt like a diver tumbling off a high cliff.

On the sofa, Barbara was slumped into the cushions. Her dress was hiked up and her underwear was showing. The bottle was seated next to her, and she swirled liquor in her glass and was fixated upon it.

"Fuzhy Wuzhy wazh a bear," she intoned.

At the wet bar Diane was inches away from Bob's face.

"I have to ask you," said Bob, "that is, I have to admit, there is a part of me that, well, it wonders...it wonders, what do I do next?"

"Fuzhy wuzhy had no hair," pronounced Barbara.

"Well, Bob, I think we have to find out just how much of a woman you are."

"And how do we do that?"

Diane was having a hard time holding herself back. There was a vibration at the core of her, and her nipples were so hot and itchy she thought her breasts were going to explode, and the dampness between her legs...oh, my.

"Well, we have to experiment a little, see if sex still turns you on."

"Fuzhy wuzhy wazh pretty fucked up, wazhn't he?"

Tell me, Bob, does the idea of sex still turn you on?

Diane was so close now that she gently stuck out her tongue and licked at Bob's lips. She could taste lipstick, and a shiver went right up her back. She felt like her nipples had suddenly turned into neon lights. If she got any wetter she was going to have to wring her damn panties out.

"I think so," Bob licked his own lip where she had touched it. He was puzzled. Of course, he had been going through a lot of changes lately.

"And do you want the Sasquatch again? Or a man, or a woman, or...or would you like somebody like me? Would you like me Bob? Do you like me?"

Up to this point Bob had been paying attention to himself, had been turned on by himself, by the changes to him. Now, however, he really studied Diane.

She was his wife's friend, but his wife was sitting on the couch and didn't seem to give a hoot's patootie what he did.

And, he had to be honest, outside of writing checks, had she ever?

But Diane hadn't ever really seemed to like him before. Her. He had even thought she was a bit dykish.

But now...now she was so close, and that eternal boner struggling against his new apparel was just shivering and shaking, and self-rapture could easily be transferred over to rapture for her. After all, her face was so close, and he could feel the slick of her tongue over his lips, he could feel her bosoms heaving so close to his own, and she had done his nails, after all.

Could he be turned on by her? Him being a woman now?

If he had been the man he once was he would have just leaped on her, pumped her mercilessly, given himself pleasure and whatever she managed to eke out of it was up to her.

But he wasn't a man. Well, he was. But he wasn't. And what would Barbara say?

Barbara was here, after all. She was sitting just a few feet away. Though, considering the state she was in it was doubtful if she would care.

So should he...she...or shouldn't she...he.

Diane had run out of patience. She placed one hand behind his neck and yanked him...her, forward.

Their lips met, and it turned all soft and gentle, as two women's lips were wont to. They nibbled on each other tenderly, exploring the lines and folds of their lips. Lipstick was delicately smeared, saliva was intermixed, and tongues began to brush against each other.

On the sofa Barbara put her head to one side and gave a snore.

Diane felt like she was swimming under water, and she could hardly breath as she ever so gently caressed Bob's breasts. Oh, the feel of them, the thrust and curve, the false nipples so carefully centered, it was all too much. And it didn't matter that they weren't real; they were real in Diane's mind.

Feeling like he was being sucked in by a whirlpool, Bob gave himself up to her lips. He closed his eyes and smelled her body and perfume, tasted her mouth like the fine cuisine it was, and delicately touched her breasts.

She arched her back, the fiery sensations coursing through her breasts and down to her womanhood. Sparks were shooting down there, and it was a wild fourth of July somewhere in the world. Between the fireworks and the dampness she knew steam was going to shoot forth at any second.

She let her hand run slowly down the fabric of Bob's dress, down to where the bulge throbbed and danced, and...the bulge was gone!

Diane's eyes snapped open.

Bob's eyes opened. "What?"

"Your erection? What happened to it?"

"My erection?" He sat back from her and looked down. Sure enough, the quivering knob that had been threatening to poke through the material was gone. "I don't know. It was there a moment ago." He sounded dazed, truly confused. He had really been into Diane, feeling the sensations, welcoming the tender, girlish ways he was slipping into. And what use did a girl have for an erection, anyway?

"Well, you've just got to get it back!" She reached for his crotch and groped him. The material stopped her efforts, and she quickly kicked her barstool away and pulled him off his.

"I'm sorry," he stuttered. "I don't--"

"Shut up and lift your dress."

She wasn't waiting for him to lift his dress, however, she was down on her knees and lifting it for him.

"But...what..."

She pulled down his panties and stared at his limp member. A moment ago, it had been a girder of throbbing steel. Now it was just a limp dick. A saggy hot dog. A fallen lump of wrinkled flesh.

Useless.

Diane surged forward. She grabbed Bob's meat with her mouth and began to work it. She pulled it, she tongued it, she sucked it, she did everything she could to make it rise again.

Useless.

Barbara grabbed his testicles and began to manipulate them. She rimmed the head desperately. Being a lawyer, she knew a lot about cocksucking, but nothing she did seemed to do the trick.

At last, exhausted, frustrated, she sat back on her heels and stared at the limp member.

Bob stared down at her. He was perplexed and sorry and didn't know what to do.

"I'm sorry, it was hard just a minute ago, it's been hard ever since I met the Sasquatch, and..."

Diane stared at his penis. It had twitched when he had said what he had said about the Sasquatch. Could it really be that simple.

"Tell me about the Sasquatch, Bob."

"Well, I was hunting, and the Sasquatch, it...."

His manhood twitched and began to lengthen.

"Do you want to make love to me, Bob?"

Immediately, Bob began to shrink.

"Do you want to get anal-ized?"

Grow, surge, erectus.

"Do you want to fuck my pussy?"

Shrink, droop, nothing.

"Asshole?"

Twitch and bounce.

"Pussy."

No twitch and bounce.

Barbara frowned. From her cross examination it was obvious what had happened. Bob actually thought of his bunghole as a vagina. To him, it was a vagina, and his little dick was merely a sideshow, an indication of whether he was turned on, but useless for anyone who wanted to be penetrated by him. Then she had a thought.

"Bob, you're an asshole."

Bob's dick bounced up.

She grabbed it in her fist and smiled.

"You're a big asshole."

Bob's dick got bigger. She pushed him down on the couch and straddled him, still holding his larger and larger penis.

"I have never seen a bigger asshole than you."

She settled down over him, felt the length of him surge up between the walls of her wet tightness.

"God, you are such an asshole!"

Bob gave a tentative lurch forward, and Diane gasped. She was on a woman, at last, and so what if she had to call her a few names to get a rise out of her?

You're a brown, smelly asshole!"

Bob pumped a little.

Diane gasped again, bent down and kissed the woman she was on, nibbled the red lips, felt the breasts, and whenever Bob slowed down, or started to get soft, Diane would just tell him he was a brown and smelly anus, a ripe bung hole, a filthy little shit giver, a toilet filler from way back.

And, Bob giving occasional moans, Diane began to shriek and beat at him with her fists. She bounced and she whimpered and she slid up and down on his pole, and when she came...when she came...it was endless, joyous, wonderful, amazing, shocking, fulfilling, mind destroying...and so on.

Next to Bob and Diane, Barbara drooled in her sleep and began snoring louder.

Bowzer
Bowzer
45 Followers
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AnonymousAnonymousabout 8 years ago
very nice

i was at a old male friend at christmas time i hand him a gift i knew he would like it was a dido cock yeas ago he show me what it feel to had one in my ass hole well he hand me a box and to me to open it and wear what in there was a bar panties nylons he then said i know you like to wear them once in awhile and it just us two here i look at them and said why not its bee years since i dress as a girl well after i got dress and went beck out to him you look lovey in that outfit i sat on the couch and he sat next to me then he put his arm around me you know i could kiss you right now i turn my head and he kiss my lips as we kiss my hand went to his cock more he kiss me the more i play with his cock now he was kissing my ear and neck soon he had my bra off and start to suck my man tits i said yes that feel good now i had his cock out out of his pants and jerking him he stop sucking my tits and said i see my girl like this just then he bend my head and my face was at his cock i open my mouth and shove it in and start to suck his cock as i did his hand pull my panties down and his finger play with my ass hole soon i felt two finger go in he was finger fucking me then he ask do my bitch want my cock in her pussy ass hole i stop and said yes sir well after that night i become his bitch

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