Harry and the Transsexuals
A Short Story by Marlene Sexton
Copyright Marlene Sexton 2012
Published by Red Heels Press
Harry had never been in this particular lounge before, but it felt familiar. The dark red carpeting, the cheap wood paneling on the walls, the dim lighting, the vinyl seating in the booths. They were all the same. These bars weren't pretty, but they were comfortable. A good place to have a few drinks, maybe a smoke and let the bullshit of the day fade away.
Harry traveled for a living and was in the last city on his schedule before heading home, just a few hours drive away. He met with clients all over the country selling video surveillance equipment. It paid well, but it didn’t seem like it did. Harry was still paying his ex-wife alimony. His wife, not exactly a prize herself, left him for another man. She was still shacked up with the unemployed loser and they were living off Harry’s alimony payments in a singlewide. The payments would cease if she married the guy, but she wouldn’t out of spite.
At forty-seven, Harry was beaten and sad. His only daughter had just graduated college and he was looking forward to a pension in a few years. His ex-wife had tried several times to attach that too, but she was never successful. He was middle aged and he looked it. Beer gut, bald spot, and a prescription for Viagra weren't at the top of many women's lists when looking for a man. He had been alone for a long time.
Harry sipped the last of his first Jack and Coke and signaled the waitress for another. He liked that about these places. Most had a waitress or two and often enough they were easy on the eyes, though Harry could admit his standards weren't all that high anymore. Unfortunately, this waitress was old enough to be his mom and was missing at least two teeth. Oh well, she was quick and attentive and Harry didn't have to fetch his own drinks.
The night slipped away as Harry had polished off three more drinks while he pretended to watch the baseball game on the TV. Mostly he just daydreamed, however. He dreamed of retirement. Getting off the road and getting to spend some time at home, such as it was. Maybe he could lose a few pounds, meet a woman, and have a real life. Even though Harry led a dreary existence, he was an optimist and hoped things would get better someday, despite the fact they never did.
As Harry called for his check, the door opened and two young girls burst into the bar. They were both tall and sexy. The one with the long blonde hair that fell from her head in big, loose curls wore a short black skirt and a shiny blue halter-top that plunged deeply between her small breasts. Black nylons covered her shapely legs and she wore tall black pumps. The other had shorter dark brown hair and wore a red sleeveless dress that came to mid-thigh. She wore tan nylons and red high-heeled sandals. Her tits were big and round and her hips were full and womanly. Her eyes seemed to sparkle.
When the waitress came over, Harry ordered another drink instead. He wasn't too proud to hang out and enjoy a little eye candy. The two girls took seats at the bar and each ordered a glass of white wine. They didn't really fit in here, but Harry wasn't complaining. They talked and laughed with each other and ordered more wine. They were both very pretty. Harry let himself imagine himself in bed with them. No need to surf porn on his laptop tonight, he had all the stimulation he needed sitting over at the bar.
Harry nursed his drink. It had been 20 minutes since the girls had come in and he really didn't want to leave. It was late, maybe eleven, but this was worth it, especially when the brunette girl started looking his way. Harry told himself it was his imagination, but then the brunette grabbed her blonde friend's attention and whispered, as they both now glanced over. Harry was a little self-conscience. Were they attracted to him? Doubtful. More likely, they were making fun of him.
After a few moments, they made their way to Harry’s booth, wine glasses in hand, “Hi, I'm Deidre,” the blonde said and then gesturing towards the brunette added, “This is Sarina. Can we join you?” Harry wasn't quite sure what to do. Part of him was screaming yes, but another part was wondering what they were up to. Was this a prank? Pull the old guy’s chain and then laugh at him. Harry decided to take a chance, but prepared himself for the worst. It wouldn’t be the first time he had been humiliated by a woman.
“Why not? Have a seat. I'm Harry.” Deidre sat to his right and Sarina his left. Up close, they didn’t seem as young as he thought, but they were both pretty.
“Nice to meet you, Harry,” Sarina said in a quiet voice.
“We saw this place and thought it looked kind of shabby chic, but it's just shabby. What're you doing in here?” Deidre asked.
“Just stopped in for a few drinks. I'm on a business trip and staying a few blocks away.”
“Out of towner, huh?” Deidre stated, “We live over on the east side of town. Sarina and I were out looking for a new place to hang. I don't think this is it.”
“No, I wouldn't think so. You girls don’t quite fit in,” Harry said looking around the place. Harry didn't get the feeling the girls were there to make fun of him. They seemed genuinely friendly. Deidre was bubbly and full of energy and Sarina seemed content just to sit and listen. They were both pretty, but different in a way Harry couldn't quite put his finger on.
“We don’t fit in a lot of places. So, you alone tonight?” Deidre asked.
“Uh...yeah, just me. I was about to head back to my room after this drink.”
Deidre put her hand on Harry’s thigh and asked, “Want a little company?” Harry had always been a little slow to catch on but he got it now. They were hookers. For a moment, he thought these girls were just being friendly. His damn optimism was always betraying him. Harry called to the waitress and reached for his wallet, but Sarina pulled his hand down.
“Harry, we're not prostitutes,” Sarina said seeming to read Harry’s mind.
“Uh...oh, no. No! Geez, it sounded like that, didn't it? I'm sorry, Harry.” Deidre apologized.
“Sorry, I just assumed. It's not every day two pretty girls introduce themselves out of the blue, you know?” Harry explained. If they weren’t hookers, then what were they and why were they coming on to him?
“Harry,” Sarina said placing her hand on Harry's thigh causing him to shift his attention to her immediately, “I just thought you looked lonely. I asked Deidre if she wanted help cheer you up and she did. That's all. I promise.”
“Look, you'll understand if I'm a little skeptical. Just seems a little odd two pretty girls walk into a dive like this, see some schmuck in the corner and just decide to follow him back to his hotel room. Just sayin'.”
The girls looked at each other, Deidre shrugged and Sarina sighed then turned back to Harry and said,” Look, you've been upfront with us. We'll be upfront with you. You just have to promise to give us a chance. Fair enough?”
Harry mulled it over for a moment. He liked both of them and honestly, he was desperate. They seemed nice enough and against his better judgment, he thought he could trust Sarina. Harry figured he'd see where this went and answered, “Fair enough.”
Sarina smiled, “OK, I'll just come out and say it, but remember, you promised to give us a chance. Deidre and I are transsexuals. Do you know what that is?”
Harry looked at Sarina, then Deidre, back again, and said, “OK, jokes on me. Look I don't know what your game is but I need to go.” Harry started to scoot to his right, but Sarina grabbed his arm and he protested, “C'mon, let go.” Harry tried to pull away but Sarina was surprisingly strong. She pulled his arm towards her. For a moment, Harry was a little worried. He wondered if they were going to grab his wallet, or worse.
However, Sarina pulled up her dress and placed Harry's hand on her crotch. Harry was a little confused, but after he settled down he realized Sarin
a wasn't joking. His hand rested on Sarina’s bare flesh. It was warm and smooth and not what Harry expected.
“See? Now you promised to give us a chance,” Sarina said. Harry looked at Sarina and then down at his hand. It was dark and he couldn't see much, but he clearly felt Sarina's cock and balls. She wasn't hard, but she had a cock, that was for sure. Harry, yanked his hand away and looked back to Sarina, his mind reeling.
“Look, Harry. What I said was true. I thought you looked lonely and I thought we might be able to help. You said we looked pretty. I promise, we don't have to do anything you don't want. Could be fun though.”
Harry looked at Deidre, “You got one too?”
“Yeah. Wanna feel it?” Deidre said and giggled.
Harry looked back at Sabrina. This was a little surreal. Even though he'd felt Sarina's cock, he was having a hard time reconciling that with what he saw. Neither girl was a perfect ten, but they didn't look like men. Not even close. Sure, they were both tall, but they were pretty too and Sarina had beautiful tits. Her eyes were just stunning. How could she be a transsexual? Harry wasn't sure what to think.
Harry had been with women he'd met in lounges before. Usually one night stands. However, this was different. These girls were pretty, but they were...well, they were men. They didn't look like men, but still. Harry was confused, a thousand thoughts running through his head. Suddenly, he had one question and asked, “Why? Why me, why now?”
“Look, I know you've got questions. Deidre and I might look like girls, act like girls, even think like girls, but we’re a lot like you. Honestly Harry, we’re horny,” Sarina said, giggled at the frank admission and continued, “You were here alone and I thought you looked like you could use a little fun. I think you're kind of cute. I wanna fuck you, OK? Deidre does too.”
Sarina took Harry's hand and looked into his eyes. She was pretty. Beautiful, in fact. He had to admit that he hadn't felt this way in years. If Sarina could be believed, she liked him. Apparently, they both did. That hadn’t happened in…well, that had never happened. Sarina’s hand was so soft and warm and looking into her eyes made Harry melt inside.
He couldn't help but trust Sarina. He didn't doubt what she said, he just wondered if he could do it. He imagined himself touching a cock. It didn't seem like it would be pleasant. However, when he thought of touching Sarina's cock specifically, or Deidre’s for that matter, it was kind of exciting. In fact, he already had and it was intriguing.
However, Harry was afraid to follow that line of thinking to its logical conclusion. He was afraid what he might discover about himself. Harry was so conflicted. On one hand, he was worried about being gay and all that. On the other hand, however, the thought of these two girls in his bed was pretty fucking hot. Not guts no glory, right?
“You promise I don't have to do anything that makes me uncomfortable? I’ve got to be honest; I've got mixed feelings about this,” Harry said deciding to see where this went.
“I promise, Harry. You get nervous Deidre and I will back off. If you can't do it, maybe we'll just give you a kinky lesbian show and a blowjob. I'm glad you’re willing to be a little adventurous, though. Who knows? You might discover it's not as bad as you think. ,” Sarina said and squeezed Harry's hand.
“It'll be fun, Harry. Promise!” Deidre said. The girls got up and Harry followed. He felt nervous, but a good nervous. He hadn't felt this way in long time. Maybe this would be fun. Besides, who would know what went on back in his room but him? That thought made Harry feel better. No matter what, it would be his little secret.
He watched Sarina and Deidre walk towards the door. He hadn't been able to tell while sitting, but now that he was standing, he realized the two girls were several inches taller than he was in their heels. They were hot, he thought as he watched there asses sway. He threw some money on the table and caught up with them. He was feeling more adventurous already.
~~~
The threesome arrived at Harry's room and Harry let them in. They had decided to drive the few blocks in Deidre's Camry. Harry was actually excited the more he contemplated the situation. Harry didn't know if he could do everything the girls wanted. Hell, he wasn't even sure what they wanted but he was going to give it a go. The room had a small kitchen, a small living area with sofa, chair and a TV, and king bed, one of those business friendly rooms.
He told the girl's to have seat and offered them a beer. Deidre wanted one, but Sarina declined saying two glasses of wine was her limit. Harry grabbed two bottles out of the fridge from amongst the Chinese takeout boxes. Harry took a seat in the chair opposite the sofa where the girls were sitting. He popped the cap off one bottle and handed it to Deidre, then did the same with his beer and took a swig. Harry suddenly thought a couple more of these might be in order.
“Thanks!” Deidre said.
“Sure. So I know it's not polite to ask a lady her...Uh, anyway, how old are you two?”
“I'm 22,” Deidre said and then added, “Sarina's 24. How old did you think we were?”
“Mid-twenties, I guess.”
“Pretty close,” Sarina said, “You don't have to be nervous, Harry. If you want, Deidre and I could undress each other. Would that take the edge off?”
“It would make me hot,” Deidre said and giggled.
Harry laughed and said, “Yeah that would be nice.”
“OK. Why don't you take of your shoes, maybe your pants, too?” Sarina suggested.
“Um...yeah, sure.” Harry had changed after work. He was in jeans, a t-shirt and tennis shoes. He kicked off the shoes and peeled off his white socks, then wiggled out of his jeans. He only had on his gray tee and his pale blue boxers.
Sarina stood up and offered her hand to Deidre. The girl took Sarina's hand and stood next to her. They faced one another and kissed, each girl slipping her arms around the other girl's waist. Harry felt his cock twitch and his balls tingled. They may have been men at one time, but watching them make out was fucking hot. Stuff like this didn’t happen to Harry. He might have wished for real girls if it was up to him, but he wasn’t complaining about what fate had tossed his way. Transsexuals or not, this was exciting.
The girls stopped kissing and Sarina looked at Harry and winked as she tugged at Deidre’s top and slipped it over her head. Deidre had no bra and really didn't need one. Her breasts were very small, little more than a swelling on her chest, but her nipples were a pleasing brown color, and hard. Deidre's skin was tanned and smooth and she had a small tattoo of a hummingbird on her left shoulder blade.
Sarina tossed the top aside, ran her fingers down Deidre’s tiny breasts, down her taught stomach, and around her wasted to Deidre's ass. Sarina unhooked the clasp in Deidre's skirt, tugged the zipper down, and pushed the skirt off of Deidre's hips. Deidre had slender hips and smooth, muscular legs. They didn't look manly, just strong and shapely.
Deidre's wasn't wearing pantyhose, but a lacy garter belt and black stockings. Over those, she wore tight, black panties of some kind of stretchy material. Harry looked, but could see no hint of anything unusual. For a moment, he thought this might have all been a joke and the girls would show him their pussies. Surprisingly, the thought was almost disappointing.
Sarina crouched in front of her friend and ran the long nails of one hand down the front of Deidre’s panties. Sarina then ran both hands down Deidre’s stockings as Harry watched intently and he could see a small bulge appear in the girl’s panties. The panties were clearly meant to keep her cock from showing. Suddenly, Harry was curious. He wanted to see more.
Sarina looked up at Deidre and ran her nails up the back of her legs, over her ass and then around Deidre's small waist. Sarina grabbed the waistband of the panties and peeled them down slowly. She was teasing Harry and it was working. He wanted to see what was in there. Sarina turned to him, leaving the panties just shy of revealing Deidre's secret.
“I don't have to do this if you don't want,” Sarina said teasing Harry. She obviously expected Harry to beg her
to continue.
“No, please. Keep going!” Harry said, more excitement in his voice than he intended.
“Are you sure?” Sarina asked, a pouty look on her face, “I wouldn't want you to see anything you don't want to see.”
Harry smiled in spite of himself. He wanted this more than he thought he would. He needed to see Deidre's cock. He was curious, but more than that, he was turned on. “Sarina, I want to see. Please?” Harry pleaded.
“I can tell,” she said, glancing at his boxers and then back to Deidre. Harry followed her eyes. His cock had found its way out of the slit in his boxers. It wasn't fully erect, but it wouldn't take much to get him there. He quickly looked back at the girls. Sarina had grabbed Deidre's panties and was pulling them down. She slid them down Deidre’s thighs, the crotch catching between Deidre's thighs momentarily, finally sliding free as Sarina continued to pull.
Down they went and Harry followed them with his eyes until Deidre stepped out of them and Sarina tossed them aside. Harry continued to follow Sarina's hands and they slid up Deidre's legs again. Sarina smiled at Deidre as she took the girl's growing cock in her hand. It was different that Harry had imagined. Harry trimmed his pubic hair, but Deidre's cock was bare, as were her balls he discovered as Sarina took those in her other hand.
The sight genuinely excited Harry. The only thought Harry had as he looked at Deidra’s cock was how feminine it looked. Though it was big, it belonged on a girl, not a man. Sarina began stroking Deidre’s stiffening shaft as Harry watched it grow. Deidre closed her eyes and moaned, obviously enjoying the attention. Harry watched as it grew longer and thicker from Sarina's soft touch.
Deidre turned to give Harry a better view. Her cock must have been eight, maybe nine, inches long and thick. Deidre's head was large and round, almost purple, her shaft thickly veined. The girl's balls were big but tight against her shaft like twenty-year-old balls should be, Harry thought. Deidre’s cock and balls were magnificent and beautiful.
“Is it so bad, Harry?” Deidre asked, biting her lower lip.
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