A Haircut & A Blowjob Ch. 01

Story Info
Taking a trim out in trade.
3.1k words
4.32
71k
15
0

Part 1 of the 2 part series

Updated 09/22/2022
Created 07/13/2003
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Author's note: I came up with the story for this idea and let it sit for a few days while I ignored writing over the weekend. On Monday when I started, the characters began creating themselves making it more of a romantic story than I had originally intended. It will appear here soon. I was a little upset since I thought the original idea still held some merit. I decided to see if I had some literary discipline and started on the story again, determined to keep to the storyline that had been outlined in my head days earlier. This time I kept to it a bit more closely.

* * * * *

"Men are all whores. Admit it." Terri tilted Jack's head to the front to trim the hairline along his neck. Every time Jack came into the shop the talk generally devolved into either the battle of the sexes or just sex in general.

"What's your point? Most people sell themselves to some degree. You sell your time to cut my hair. I sell my time where I work. Most people don't get to take advantage of what they do best, sadly. Wouldn't it be great to be able to barter your best talent out to others?" At her urging Jack tilted his head to the side.

"What would that be, in your case?" Terri was both expectant and a bit sarcastic. She could imagine what was coming. Jack did not disappoint.

"Oral Sex with women, of course. Talent this great can't go for just pennies though." The shit-eating grin on Jacks face could not help but make Terri laugh.

"I'll admit it is a great talent to have, but I don't think you'll find much call for barter big boy." Jackie had stayed behind to talk with Jack and Terri before she closed the shop. "On that note though I will bid you both a good evening. Terri, don't let him try to swindle you out of the cost of that haircut by promising a mouth full of ecstasy, okay? You can get what he's promising at the club tomorrow night, and they'll pay for your drinks."

Jack and Terri said goodnight as the shop's owner left them alone. The conversation left with her for a while. Terri could not believe she was actually considering the conversation seriously. She moved around Jack slowly finishing the haircut. After five years she could almost do it in her sleep. Tight on the sides, a little less so on the crown, and leave enough in front so he could throw it to the side. It was not the first time Jack had said something that played on her mind. She felt a little slipperiness starting by the end of the haircut.

Maybe if I dared him, called his bluff, she thought to herself. A little smile played across her lips as she led him to the sink to wash away the clippings. She imagined her little conspiracy. I'll relax him with a shampoo massage then spring it on him during the rinse. She set her hands to work rubbing his head. After five years washing and cutting hair Terri knew how to massage a head. It was always a little extra kick she threw in and usually kept the tips flowing all day. When Jack sighed she knew she had him.

"How about we take this haircut out in trade tonight?" Terri's smile was bold and sardonic. The perfect I dare you stare. Jack's eyes opened and he choked a bit. Perfect, Terri thought.

"Hmmmm," Jack stalled. He needed a moment to think. A one-second assessment of Terri, more memory than active looking, reminded him that Terri had everything he wanted in a woman's body - except him. She was tall, but not taller than Jack. Terri is 5'9 with dark curly hair that she kept cut short. Her nicely sized breasts appeared firm in the T-shirts she usually wore when cutting hair. After curving in a bit her hips flair out to a nice child-rearing size, but the backside of those hips did not nearly reach ghetto booty proportion. Jack had always imagined it would be firm since Terri's arms were always tight with a nice triceps cut. Her legs were no less amazing showing perfect swimmer's muscles all the way up to her hips when she wore shorts to work in the summer. Now Terri's silver gray eyes were bearing down into Jack's waiting for an answer.

"I don't know. It seems like an awful lot to do for just a haircut. I think I'll need some change back." Since we're bartering, he thought. The shit-eating grin came back brassy and confident. Terri bit.

"What kind of change? You know it's not like I let everyone do that to me, you know." Damn, I keep forgetting guys take dares, Terri thought. Still Jack was a good guy and he would let her out of it, she told herself.

"The change would be one blowjob payable ahead of time." Jack was starting to sweat a bit now. Could she be serious? It would be great, but it took a long time for me to find someone who cut my hair as well as she did, he thought. She'll back down or give me room to get out of it. C'mon, laugh and we'll chalk it up to me bragging again. Terri did not laugh. She remained looking down at him the sarcastic smile frozen on her face.

Is he serious, Terri asked herself? Her thoughts turned in that direction figuring she'd shrug it off. But hadn't Jackie gone out with Jack for a few months? She suddenly wished she didn't remember all the girl talk that came flooding back into her mind. A spotlight highlighted Jackie's description of one time he went down on her.

"He tied my hands up to the head board. He said he didn't want them to get in the way. He also told me the best always start at the top and work their way down. The things he did. I don't know how many times I lost track of where he was. I must have cum four or five times - intensely." Jackie had told the story a few times and always looked a bit sad for a few moments afterward. She'd later told Terri just how intense it was being with Jack and not just the sex.

The dilemma created a silence filled by the thoughts of each person. Terri was indeed starting to treat it seriously and Jack had placed the opening firmly in her hands. I'm not going to just fall on my knees in front of him though. Let's see if I can make him sweat a bit. Don't want him to think I'm too eager. She laughed.

"Your hairs a bit dry. I think I'd better use some extra strength conditioner on it. I'll have to cover your eyes since it's pretty intense stuff." Terri draped a towel across Jack's eyes. The conditioner she applied made Jack's scalp tingle more than usual. He bought it, she thought. Now to 'Jack' up the pressure. Terri swung her leg over the seat where Jack reclined. Her hips sunk naturally into the right place on his lap as she folded her arms to lean against his chest.

"Now why would your particular brand of face be so good that you could hope to earn a blowjob as change?" Terri purposefully got up close to Jack's face when she spoke. To her pleasure he didn't try to pull off the towel when he answered.

"You'll understand after the second orgasm. Actually I'm offering quite the bargain, you being a friend and all. Anyone else would cut my hair twice AND blow me. For you, my lips are on special." Damn she's warm, he thought to himself. He imagined she was wet too. Even without these thoughts her seat and the occasional brush of breast under her arms would be enough to get him started. Any attempt at adjustment would give it away though. That or another minute, he figured.

That's it, she thought, time for me to put up or shut up. Terri spent an indecisive minute and then she felt him. An increasing pressure pushed against her where she straddled him. She slid down his legs seemingly before she made the decision. Her hands searched out his belt and loosened his pants. Jacks hips lifted off the seat to make it easier to pull his pants down. He lifted again a bit higher pressing himself against her face accidentally. He felt her cheek pressing against him momentarily. She pulled his hands away when he went to pull down his boxer briefs. His hands went back to the armrests.

Terri looked up to see the towel still over his eyes. Her smile was wicked as her attention was drawn back the tented gray underwear. She teased him by playing along the waistband. She let the backs of her fingers tease his skin making him think she would pull them down. At the same time she teased herself making imaginary bites and kisses just over his hard cock. She grabbed the waistband as if to pull it down but to Jack's surprise she pulled it up. Not long after he felt her hand slip into the fly.

Jack moaned as Terri ran her fingertips through his hair, fingers split around his cock. The sides of her fingers stroked him lightly. The kisses and nibbles were starting to make contact as her hunger for him started to increase.

Jack felt her mouth through the cotton. At first she just used her lips on the underside. She gradually moved up to the tip where he felt her teeth. Her hand was stroking the underside with her palm. Terri's other hand was gently juggling his balls from the outside. She opened his fly wider and pulled his cock out. She studied it as her hand moved slowly up and down. Her hand was so slow and gentle it seemed more like she was petting him instead of stroking.

Terri let him go for a moment opening the fly a bit wider with both hands and pulling down. His balls popped through joining his cock in her gaze. A quick peek told her the towel was still in place. She didn't have to hold back her smile or her fascination. Her fingers massaged his balls as softly as the hand that resumed the massage of his cock.

Jack's body jerked and shivered from the tickling she was giving his sac. Terri nearly laughed enjoying a sudden feeling of control over Jack. A feeling, she realized, he would soon have with her when he took up the same position. A sudden desire to squeeze her breasts together overtook her. A moan brought her out of her reverie.

Terri started at the base where his sac wrapped around his cock. Her tongue pressed the crinkled skin down feeling the solid pressure of his organ. She momentarily held Jack's cock still as her tongue gently lapped at him no higher than two inches from the base.

Her tongue moved down taking over juggling his balls from her hand. Terri felt Jack tighten up as she took one of his balls in her mouth. He was safe. She always saved her aggression for a different task. Her tongue danced around as she applied a light suction. His cock was completely hard now. Not that she could be sure exactly when that had happened.

Terri began gently stroking his cock again. She did not take the other nut in her mouth instead choosing to slather it with her tongue in long strokes. Jack could not help but think of popsicles and lollipops. Her mouth pushed his balls up and apart as her tongue began stroking the base of his cock.

Her tongue started exerting more pressure followed by her hand. Terri began milking his shaft. Pressure exerted as she stroked it toward the tip, a gentle caress as she moved down. After a few strokes up she had what she wanted. Jack felt her fingertip work around the head of his cock. It seemed to move a little too easily until he realized why.

Terri's tongue left the base of Jack's cock as she began the upward milking once again. The head of his cock glistened a little although the fluorescent lights didn't really do the dampness any visual justice. She studied it a bit more squeezing out a bit more fluid. When it began to form a drip she moved to catch it.

Jack felt her tongue dab at the head. He could already feel the tingle starting. Terri was earning a special effort. He could imagine her tasting it then swallowing. More of the licking followed as she cleaned the head. The tip finally broke through her lips as he felt the first bit of suction.

His moan brought Terri back to the situation. She had let her concentration hypnotize her a little. Change, she asked him silently? The circle of her mouth had a slightly sarcastic turn at one corner as she took him deeper into your mouth. Out of the corner of her eyes she could see his hands opening and closing. She knew he wanted to bring them to her head. Time to up the ante, she thought.

"It seems like you're enjoying this quite a bit. Jackie did tell me to make sure you paid for that haircut. Does this deal come with some kind of guarantee?" Terri stroked him firmly milking a bit more clear fluid for herself.

Jack was in turmoil. Terri had him, if not by the balls by his dick at least. He didn't think she would leave him there undone, but she now held the higher position. Her tongue swiped his tip reminding him of the question at hand. His grin came back again.

"If by the time I'm done you believe there has not been enough satisfaction given to equal both the haircut AND the great things you are doing to me right now I will pay for the haircut. Should you be completely unsatisfied with the entire experience I will throw in dinner at your place of choosing." He was not sure Terri would want dinner with a guy that failed to get her off with their tongue but it seemed a nice, if unnecessary, gesture.

Terri was also not sure if dinner would be a good thing if his face were a miss. She liked his confidence and bent to her task. She loved the noises Jack was making as she took him deeper into her mouth. Her head swayed side to side as she slowly sucked her way to the tip. A gentle rubbing of her teeth brought back a hint of the tension displayed when she had played with his balls.

She began bobbing her head up and down. Jack could imagine her, mouth wrapped around his cock. He could almost see Terri's eyes looking up at him. They were looking at him at just that moment. Terri wished she could look up into his eyes as she took his cock completely into her mouth. She told herself it was mostly to see the look on his face. Mostly.

Instead she was treated to something else that surprised her. His mouth was moving. Jack's tongue seemed to be unsuccessfully wetting his lips. The look on his face alternated from helpless, to fierce, to the point of wanting to lose control. His hands took on the shape of her head more than a few times.

That's the signal, Terri thought. When he grabs the armrests is when he'll go. Either that or when he grabs my head. Not that she would mind it if that happened. The next few dives over his cock were through a mouth trying hard to smile.

The tingle in the base of Jack's cock had moved all the way up the shaft as Terri took him inside her mouth fully. The way she closed her mouth over him and pulled in her cheeks made his cock feel completely surrounded. Her tongued cupped the underside seemingly all the way to her throat.

Terri's head began bobbing faster. Fast or slow did not matter to Jack. He was close and she could do just about anything but stop to make it happen. His hands grabbed the armrest, knuckles white.

Terri was pulling back when she saw her sign. She pulled out to the tip and gave one long evenly paced dive concentrating on giving as much contact with her mouth as possible. She felt his head grow.

Jack yelled out and moaned. The last entry into her mouth had done it. The pleasure spread out from his cock down his legs and up his belly. He barely noticed that Terri still had his cock in her mouth. Her throat worked to keep up with his jerking cock. Two swallows left her with enough to taste and show him.

The light was bright in Jack's eyes as Terri moved the towel. He brought his head up to look down at her. The silver gray eyes were looking directly into his. Terri opened her mouth showing the white fluid coating her tongue. For good measure she stroked a few more drops to the tip of his cock. Her tongue did one final Popsicle lick, clearing the drop from the eye.

"You've got your work cut out for you," said Terri. She stretched her legs out before getting up.

Terri remembered the conditioner and began rinsing his hair as he buttoned up his pants and pulled the belt tight. She dried his hair with a towel. Jack's breath was slow and even. For some reason she was glad his eyes weren't open at just that moment. The tension she had felt prior to going down on Jack was already twice what it had been.

Jack was completely relaxed. It was quite simply the best he had ever had. The look on his face was almost angelic to Terri. She thought it must be what it was like to watch him sleep. His eyes opened shocking her. The smile on his face weakened as he saw her eyes move away from him. He whispered something to her she could not hope to hear. As she stooped down asking him to repeat himself he pulled her head down further.

Her mouth had his flavor in it as expected. Still he felt it his duty to thank her with his kiss. He thanked her deeply, softly, gently and roughly. His lips thanked her until her heard a little moan pass through them. As their mouths parted he felt her breath against his face.

Terri's eyes immediately met Jack's as she opened them. The smile was gone. Another look she couldn't describe had replaced it. He licked his lips as his hands once again brought her face close.

"Now it's your turn..."

- To be continued...

Please rate this story
The author would appreciate your feedback.
Share this Story

READ MORE OF THIS SERIES

Similar Stories

That's What Friends Are For Justin's best friend Samantha will do anything for him. in First Time
The Blowjob Girls: Morning Hunger Two best friends adore giving blowjobsin Erotic Couplings
Blowjob Revenge After boyfriend calls her cocksucker, she blows everyone.in Group Sex
A Friendly Blowjob She makes him jizz his pants and sucks him off to make it upin Erotic Couplings
The Virgin Blowjob Queen Virgin girlfriend likes to suck dicks.in Exhibitionist & Voyeur
More Stories