tagTranssexuals & CrossdressersHelen and Jim Vol. 01

Helen and Jim Vol. 01



Angel sat with her arm around her friend Helen consoling her as she sobbed quietly.

"Helen honey, he was a jerk. Certainly not worth crying over! You should be glad you found out he was cheating before you moved in together. At least now all you have to do is change the locks on your doors and throw his tooth brush in the trash."

"But I love him!" She sobbed "He made me happy when he was around me. And the sex was pretty good too!"

"Yea, but you told me he couldn't handle all of you and he was still a jerk sometimes. I'm telling you, there is someone out there who is a much better match for you."

"But I'm tired of this whole dating thing. I want a steady boyfriend that I can count on and if it could last awhile maybe even marry him."

"Marry him? Are you crazy?! You're still young and beautiful, why in the world would you want to settle down now? You can pretty much have any man you want!"

"Sure, as long as he doesn't mind me wanting to stick my cock in his ass all the time. Oh Angel, at least Willie was...well...willing!"

They looked at each other for a second then commenced to snicker. The snickers morphed into chuckles and then the whole thing dissolved into laughter. They laughed, leaning against each other until tears were running down the cheeks of both women. Wiping their eyes with the heals of their hands they slowed back down to chuckles and Angel said,

"Good ole willing Willie. That's how we'll remember him. He was willing, not much of a boyfriend in any other category, but at least he was willing to give up his man butt!"

"Well most of the time anyway."

"Oh shit Helen, you used to bitch about him not putting out enough for you and now you're defending him. I know it sucks to be dumped, at least that's what I've been told, because I've never actually experienced it myself, but you're just going to have to get over it." Angel said with haughty air, her chest puffed out in mock pride.

Helen elbowed Angel in the ribs, deflating her and making them both chuckle some more.

"All teasing aside, the best way that I know of to get over being dumped by some overrated ex-boyfriend is to go out and find some other willing guy and get laid. Nothing makes you forget about an old asshole as quickly as having a new one quivering excitedly around the base of your girl prick! What'd ya say hon, to the clubs?"

Helen wiped her cheeks, sniffed and put on a brave smile. She thought for a second then nodded and said,

"To the clubs."

Angel gave her a blinding smile and huge hug. She stood up and said,

"Woohoo! Look out boys, Helen's on the prowl and no behind is safe! I'm going to run home and slip into something a little more likely to give me the edge to slip into someone and I'll be back to pick you up in a couple of hours." She consulted her cell phone for the time and said, "Say around 9:30? That will put us in the clubs around 10 when things are really jumping!"

"Sure Angel, I'll be ready at 9:30."

Angel held her hands down like she was holding onto someone's imaginary waist and thrust her hips a couple of times as she said,

"I can't wait to do some dancing tonight! We're gonna have a great time!"

Angel leaned down and planted a quick kiss on Helen's forehead then spun on her flip-flop covered heal and sashayed out the door. Helen watched her go and couldn't help but to feel a little out classed. Angel was wearing snug ripped blue jeans and a white tee shirt speckled with pink paint, yet somehow still looked like a supermodel or more appropriately some golden goddess. Her long blonde curls bouncing on her shoulders, her smooth tanned legs enticing through the rips in her faded blue jeans and that was how she looked when she was dressed down! Helen knew that tonight when Angel picked her up she would look like she'd stepped out of a fashion magazine.

Helen looked down at the old grey sweat pants that covered her legs and the baggy Megadeath tee that had been someother old boyfriend's from before Willie. At the thought of Willie tears began to gather in her eyes again so she pushed the thoughts of him away and got up off of the couch to shuffle into the bedroom, pulling the tee off in the hallway as she went. She threw it on the unmade bed, shucked the pants off and added them to the tee, then went into the bathroom to grab a shower before dressing.

Helen stood before a full length mirror attached to the back of the bathroom door and appraised her body. She had a decent figure. Her breasts stood up nicely and having a pair of 36Ds meant there was plenty to play with. She had sultry brown eyes and a trim waist that capped off a pair of full hips. She was very curvaceous in all the right places so why the hell did Willie suddenly lose interest? Maybe it was because she was becoming so comfortable with him that she'd suggested they move in together. It wasn't her body he was running from, it was the commitment. She sighed and pouted out full lips beneath a petite nose as she pulled a lock of her dark hair back behind an ear. All this and a tick over 8 inches in her panties to give a guy a real thrill, it was Willie's loss. She knew Mr. Right was out there, she just needed to find him...or he needed to find her.

Helen reached into the shower and turned on the hot water. She shucked her panties off and stood over the toilet to take a long needed piss into the bowl. It splashed a little, but she had put up the seat like a good girl so it didn't really matter. When the last few drops dribbled out of the end she shook it a couple of times, then opened the door to the shower and disappeared into the steam.


Jim was a nice guy and pretty good looking to boot. He had blue eyes, dark brown hair, and he had the smile of a cover model. He sported a nicely muscled frame and at a half inch over six feet tall could pull off that whole 'tall dark and handsome' thing pretty well. On top of being nice and good looking he was quite the handy man, adept at plumbing, carpentry, electrical, tile work or any of that construction type of stuff. Need your old car fixed? Jim could handle that as well. He could sew up a medieval costume for a Renaissance Fair or cook up a fine candle lit dinner for two or ten. Laundry? No problem. Hell he would even clean the entire house...including the windows! But he couldn't keep a girlfriend.

Jim was about as close to Mr. Right as a woman could get, yet once she became intimate with him the deal fell through. He would romance the hell out of some woman and land her in bed only to have her bounce right back out the other side. With all that Jim had going for him he had one major drawback. No, he didn't fart excessively during sex or pick his nose, well...only if it really needed it. He just came up a bit...uh...short in the penis department. Ok, quite a bit short. If you really must know, he was somewhere around the length of the average man's pinkie finger. Yep, that short. If the little rascal had been the diameter of a tuna can things would have worked out fine, but that was not the case.

Now Jim had enough good things going for him that if he looked long enough he surely would have found a woman willing to over look that one short coming, pun intended, for all of his other good traits, assuming he was willing to put his tongue to work in place of his penis. Which of course being Mr. Right and all he most certainly would have done. However, after a long string of comments such as, "Oh wow! That's really small!" and "My, what a cute itsy, bitsy penis!" among others, he had sworn off dating. He'd even had one girlfriend whose clit was bigger than his penis when she took a vacuum pump to it. They might have made a go of it, but she constantly teased him about it and at 22 you don't find much humor in the fact your girlfriend is hung better than you. He broke that one off himself.

Time passed, as it has a way of doing without our notice and one day Jim woke up and realized that his thirtieth birthday was just a couple of weeks away. The big, Three-OH-shit-what-am-I-going-to-do-now, birthday. Jim sat on the edge of his bed, head in his hands as he contemplated his past and what the future could possibly hold. Maybe he should take another stab at the mating game. Maybe he should turn gay and find him a nice guy to settle down with, but there was one major problem with that, he wasn't attracted to guys in the least. Maybe he should just become a monk, but he'd heard some stories about those guys...so nope. Not that either. So now he was back to women. Maybe now that he was older and the women would be as well, they would be more understanding and caring. Well maybe, but maybe not.

Brave was now another trait Jim could add to his long list of pros as he walked timidly into a noisy club called Toppers. On the sign over the doorway was a picture of a top hat, cane and white gloves, but to Jim's relief those symbols didn't really express the club's dress code. He had been expecting to see many of the patrons dressed formally, but they were all dressed as they would be for any dance club. He was also relieved to see that the crowd not only appeared to be at least around his age, but there were women everywhere. On the dance floor, on the stage, on the bar, hell it looked like the world's largest bachelorette party. Sure there were guys too, but the ratio was way in favor of the guys seeing as most of them were dancing with at least two women. If he'd been just a tick more observant he would have noticed that a few of those women, though very glamorous at a distance, had rather manly features up close.

Jim worked his way to the bar and finding a seat on the end plopped into it and hailed the bartender. The guy had on all black with a matching bowtie and was obviously very fit. They couldn't really communicate over the throbbing techno music so the bartender had Jim point out his choice on the drinks list. Once Jim had his Dos Equis in hand he turned to watch the dance floor and sip on his liquid courage as he looked for a potential dance partner.

The Girls Go Out

Helen smoothed down the little black dress as she appraised herself in the mirror. The dress clung to her curves and made her look like a modern version of Bettie Page, the world's most prolific pin up model. Helen's dark hair even had a fifties flair to it that matched the old pin up styles with bangs along the front and a long cascade of dark curls down over her shoulders. She'd copied it out of a Hot Rod Deluxe magazine that had been a recent impulse buy at the grocery store. After all, she kind of liked the look of the fifties and she really dug all those old school street rods and even a few of the rat rods. She would love to go out cruising topless in one of those old cars. The car not her, but under the right circumstances, she could probably be talked out of her top as well. She flashed a mischievous grin at her reflection and it was returned with a sparkle in its eyes. She slipped into a pair of black thigh high stockings and attached them to the garter belt. Some black retro pumps with red soles that matched her lipstick and nails rounded out the look. With one last turn before the mirror she strode from the bedroom armored in confidence on the outside, but still a little shaky on the inside.

Angel was right on time and sitting at the curb in front of Helen's house when she peeked out. Helen opened the door to waive to Angel before she gathered up her purse and keys to dash out to the bright red convertible M3. As she stepped up to the side of the car Angel asked,

"Wanna drive?"

Helen hesitated for a second and looked the red cabriolet up and down. It was a nice car but didn't really move her much. She liked the old stuff. Helen shook her head and hopped into the passenger seat.

"Oh come on!" Angel said with exasperation. "This is a really nice car. When are you going to get over this old style kick you're on? You need to get with the modern times, and look at your hair! I swear it looks right out of a fifties magazine! Last chance, wanna drive?"


"Ok, your loss."

With a quick look over her smooth tanned shoulder to check for traffic she revved the M and left the curb in a slight haze of white tire smoke, snatching gears as she followed her headlight beams into the darkness.

Angel pulled up to the valet station at the club and one of guys stepped smartly around to the drivers door and opened it for her as he said,

"Mistress Angel! It is always so nice to see you. Now I wish I was working inside tonight!"

Angel slipped out of the driver's seat in a silver strapless dress that shimmered under the clubs lighted sign reflecting back all the many colors of the neon. The dress flowed into place like liquid metal with a hem that hung just shy of the middle of her silky thighs. Thighs that needed no hose or stockings Helen noticed with a sigh. Helen started to open her own door when a smiling young man said,

"Let me help you with that." As he proceeded to hold open the door and take her hand to help her from the car he got a flash of her garters. "You look very beautiful tonight miss. You could have stepped out of one of my Kar Kulture magazines!" Helen looked at the young guy a bit closer and noticed that he was sporting some ink though it was mostly covered by his clothes. With his black rimed glasses and flat top hair cut it was easy to see that he was also into that whole retro scene.

"Thank you! I'm glad you approve of my outfit." She shot a meaningful glance at Angel who had stopped talking with her valet to watch the interaction. Angel rolled her eyes as she returned her attention to her valet and said,

"Tony you always say the nicest things to me. If you're still on duty when I leave maybe I'll give you a special, more personal, tip when I pick up the car. Would you like that?"

"Oh yes Mistress Angel! That's more than I could've hoped for!" Angel rested her hand on his muscular chest for a moment as she gave him a peck on the cheek, then stepped around him and headed for the front door. Helen flashed a smile at the young man holding her door before she too stepped onto the sidewalk to follow Angel. When they reached the heavy brass door a muscular black bouncer pulled it open for them and said,

"Good to have you with us again Mistress Angel."

"Thank you Gerald. It's good to be back." As the two ladies moved into the atrium Helen asked,

"What's up with the whole "Mistress" Angel thing?"

"I swear, one very well made Halloween costume and too many shots of Jose' Cuervo can leave you branded for life!" Angel said with a dismissive waive of her hand. They went through the inner doors past two big burly men with long beards that could have passed for the Gibbons brothers from ZZ Top. They were wearing dark Ray Ban sunglasses, their barrel chests stretching the expensive suit material. They were as motionless as Buckingham Palace guards when the women passed. Angel walked by them without a glance; however Helen couldn't help but sneak a peek at the one on the right. She thought she saw the corners of his mouth twitch toward a smile, but twitch was all they did.

Inside the joint was jumping. The throbbing techno beat pushed and bullied the dancers around the floor while lights pulsed and whorled in time to the music. Men and women were moving and rubbing against each other, swept up by the erotic music and well lubricated by liberal applications of alcohol. Hands groped, hips gyrated, crotches ground, breasts and partially bare chests trickled with sweat. It was truly a target rich environment.

Out of the crowd materialized a muscular man in black slacks and a black wife beater undershirt with a bowtie around his neck, the standard uniform for the Topper's staff. He didn't attempt to talk over the music. Instead he reached for Angel's hand and bending at the waist pressed his full lips to the back of it in a genteel kiss. They were warm and so soft they caused Angel's panties to tighten as she thought of them sliding along her rigid womanhood. He stood and indicated with an exaggerated waive of his arm that they should follow him to their table. They worked their way through the crowd to a reserved booth in a darker corner of the club. The table was in an alcove with two heavy red velvet curtains that could be pulled together if the people in the booth desired a bit more privacy.

Angel tossed her clutch on the padded table then turned to survey the room as she leaned against its edge. An Asian waiter glided up to the women just as the music stopped.

"What can I get you ladies?" Angel changed her attention to the waiter and was pleased to see that he was built like Jett Lee. It was obvious that he worked out and his easy balance seemed to shout that he was far more dangerous than the two mountains of man flesh that were guarding the inner doors.

"I'll take a glass of Chardonnay. Helen?"

"Bottle of beer. Dos Equis amber with a lime."

"Bring us a bottle of Champaign too. The Dom. We're celebrating Helen's escape from a boyfriend that didn't put out enough!"

The waiter smirked and said,

"Congratulations on your escape! I'll bring your order right out and I believe the Cheer Up Committee is already on the way over."

Before the music started up again Helen just had time to ask,

"Cheer Up Committee?"

As the throbbing new song started Angel pointed back toward the bar at three men dressed in the house uniform who were working their way over to Helen and Angel. The all looked like they could have been on a Chippendale's calendar. When the lead guy arrived Angel pulled what appeared to be a credit card with the Topper's logo on it out of her purse and flashed it to him as she pointed to Helen. With a nod he turned and dropped to his knees in front of Helen. Before she could protest he'd lifted the hem of her dress and freed her flaccid penis from its confines. He took her in his mouth and began to roll her around with his tongue as he sucked on her. Helen stiffened. First her body in shock as she controlled an urge to push him away and then she began to stiffen in his mouth. It started slowly at first, but as she began to harden in earnest she quickly outgrew his mouth. He gagged and snorted as he tried to accommodate her, but the girth was just a bit more than he could handle. Helen couldn't help smiling as she watched him struggle with her. Rare indeed was the guy who could swallow her without a little practice, but this guy was gaining ground quickly enough. He took a deep breath through his nose and sliding his hands up along the back of her smooth thighs to grip her firm round ass, proceeded to tilt his head back and swallow the length of her. Helen's eyes closed and her knees went weak. Somewhere in the back of her mind she thought it was a good thing the other two guys were there to help hold her up. After all, deep throat isn't something a girl her size gets very often!

Helen felt a hand searching for the zipper to her dress, then felt the squeeze of the fabric loosen when the hand found its mark. She didn't have names for these guys so she improvised by giving them month names since they looked like calendar models. Her engorged penis was still engulfed in Mr. December's throat and she couldn't help but wonder just how long he could hold his breath. Mr.'s June and July had the top of her dress down exposing the smooth black demi bra that cupped her voluptuous chest. That same searching hand, or perhaps a different one, found its way to her bra clasp and with a practiced ease freed her breasts. Somewhere far away she heard Angel say,

"I think I should leave you and your new found 'Cheer' alone for a while!"

Helen was lost in a world of calendar worthy body parts and could only manage a very short waive as Angel pulled the curtains closed. Swamped in unearthly male beauty Helen thrilled as mouths and hands found every erogenous zone. Her body was their playground and they romped and played as they explored her. Titillating her with their suckling mouths on her balls, toes, nipples, fingers, and any other body parts they could reach. They all worshiped her mighty womanhood and at one point in time they all three were licking along the sides of it. All of them were respectably hung, but only Mr. December came close to Helen's size. At some point the table had become a bed and Mr. December was straddling Helen's thighs holding both of their cocks together in his hands as he stroked them. She looked past June and July's heads where their busy mouths were working on her nipples and into December's eyes. His desire for her was written plainly on his face. His hands were longingly caressing her prick which was the same length as his, but thicker.

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byruwild© 16 comments/ 140838 views/ 89 favorites

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