Karen Takes a Dare

Karen Takes a Dare

Karen couldn't believe she was doing this. She was about to walk down a busy street in a not so nice part of town all because of a dare she had made with her best friend. Nancy, Karen's best friend, could be a bit of a slut and Karen knew it. Nancy also knew that Karen could be a bit of a prude and needed to let down her hair.

The two friends had been debating for weeks about how if Karen would just relax and do something out of the ordinary, she might loosen up a bit. Karen was never able to sustain a relationship. It seemed that whenever she got close to a guy, he would want her to do something as simple as sucking him, and that would be the end of the relationship. Karen knew that she should just do it, but the act seemed so animalistic she couldn't bring herself to do it. Nancy had told her for years to just branch out.

Finally, it had come down to the bet. Karen knew she needed to loosen up a bit or she would never find a man. At 33 she knew she was still attractive, but how much longer would that last. Her 34d breast were starting to sag a bit, it was only a matter of time. She worked out and kept her 5'6" frame at 125 pounds but it was getting harder.

Nancy never had trouble finding dates. Guys flocked to her. Karen knew she was prettier than Nancy but there was something about Nancy that made guys come to her like a moth to a flame. Karen knew it was the animal attraction of sex appeal. Guys knew that Nancy was adventurous, that was a nice way of putting it, and wanted to be with her. Karen knew that Nancy had experience in all three holes, because Nancy told her every detail, and Karen had to admit it made her hot.

When Nancy told Karen how she would run her tongue around the head of a guy's cock, Karen would blush, but it excited her. When she told how the guy exploded in her mouth and she had to swallow or drown, Karen felt her mouth water a bit. When told about how the guys thick, hard cock thrust into her hairless pussy, Karen had a full bush, moisture flooded Karen's pussy. The description of the guy's cock penetrating Nancy's asshole, stretching it to the limit, made Karen's asshole flutter.

Nancy told Karen everything about her sex life. Karen knew things about guy's cocks that she shouldn't. Whose was bullet shaped, whose mushroom head, whose was like a banana and rubbed the g-spot just right, and whose twisted right or left. She also knew that Matt's was huge. Whenever she ran into one of these guys, Karen's nipples hardened as if by their own accord.

Karen knew Nancy was right but she needed an excuse to let go. The dare allowed her to do it. The deal was if Karen walked down this street, actually four blocks and then down the alley, exposing herself to men she saw, Nancy would take her on an all-expense paid weekend to a spa. If she chickened out, Karen would have to not only make Nancy's car payment but also hide in the closet while Nancy entertained one of her males. Karen wasn't sure why she had taken this dare, but she did.

The deal was that Nancy would help with the outfit as she had more to choose from. She would then drive Karen to the point of drop off and then drive to the end pick-up point and wait for Karen to "run the gauntlet," as Nancy put it. The outfit Nancy chose featured a balconette bra made from sheer lace, matching sheer thong which revealed Karen's hairy pussy, garter and stockings, 2 inch heels, and over the top was a Kimono style coat that came to mid-thigh.

Before completing the outfit with the coat, Nancy told Karen this just wouldn't do. She directed Karen into the bathroom and told her to lose the panties. "Why?" Karen asked but she was told to "DO IT!" Once in the bathroom Nancy told Karen she could keep the bush but she needed a bit of a haircut. Nancy approached Karen, put hands under armpits and helped her onto the bathroom counter next to the sink. She then grabbed some scissors, razor, and shaving cream.

"You didn't say anything about shaving," Karen protested but went along with Nancy. Nancy spread Karen's legs and carefully used the scissors to trim the hair along both lips and down to the anus. Karen was in a state of shock. She couldn't believe her friend was this close to her vagina and she could feel herself getting arouse. Not only that the scent of aroused female was evident to both.

"Don't worry," Nancy stated. "I won't cut you and I'm aroused, too." She then used the shaving cream and coated the area she had just trimmed. Karen leaned back against the mirror and closed her eyes. When the cold blade of the razor made contact she couldn't hold back a moan. Nancy continued to shave the area, leaving it bald for the first time since pre-puberty. The only remaining hair was a tuft above the slit. As she finished, Nancy took a wet wash cloth and cleaned the entire area. She then took a middle finger and gently stroked Karen's clit, causing her to push her pelvis forward. Nancy knew Karen was going to be fine tonight.

With the panties back in place, the lips now completely visible through the sheer material, the Kimono coat was put on, covering all but leaving easy exposure as well.

As the two drove to the drop-off spot, Nancy reminded Karen what she had to do. Since it was 9:00 and just getting dark there were bound to be some out and about but there shouldn't be the nightly homeless visitors. Karen was to walk down the route. As she came to someone, she had to expose herself. If they asked to see something, she must comply. She could refuse if they tried to touch if she wanted. Once down the four blocks, she was to turn down the alley. At the end of the alley, Nancy would be waiting.

"Any questions?" Nancy asked. Karen shook her head. Nancy then reached over, took Karen's chin in her hand, and turned her face. Looking into her eyes, Nancy gave Karen a sensuous kiss, lowering her hand to the juncture of Karen's thighs and pressing up and inward to make sure pressure was placed on her clit. Karen's eyes closed and her mouth involuntarily parted. As tongues touched, Nancy pulled away and said, "Have fun."

Karen opened the door and exited the vehicle. She could feel the cool night air on her bottom. She looked back into the vehicle as she closed the door, giving Nancy a nervous smile, and began down the street.

There was no one for the first half a block and Karen thought, "This isn't too bad." At the two-thirds block point, she ran into her first person. A middle aged male was leaving his building. As he closed the door behind him, he saw Karen approaching. Normally, he would have been a bit apprehensive. You kept an eye on people on this street, but Karen didn't seem too threatening.

As she approached him, she thought, "Well, here goes nothing," and undid the sash that tied the coat closed. Remembering the dare, she quickly pulled the coat open, revealing herself. The first thing he saw was her hardened nipples, pushed up by the bar. He quickly looked down to find the scant coverage of the panties, the lips of her pussy, and her lovely legs.

"Thank you, sweetie. Not sure why I'm so lucky, but this is a pleasurable sight." He then walked past her and down the road.

"Thank god he didn't ask me for anything," Karen thought on shaking legs and covered herself. "If everyone is like him, this won't be too bad." She continued down the street with a new confidence.

At the end of the first block Karen came to an entryway where a male was laying on the front stoup. He appeared to be in his early 60's and judging by the bag next to him, he was homeless. "I was hoping it was too early for any homeless to be here," Karen thought as she approached. She could smell a combination of alcohol, unwashed male, and urine. She knew this would be a greater test than the last.

She stopped in front of the man and he looked up. The street light had just come on at this corner and was illuminating her. The man grunted acknowledgement of her presence and she untied the sash to reveal her body to him. She could see that he was near her father's age and she was unsure if that was good or bad.

As her torso came into view, the man sat upright. He could now clearly see her breasts, panty covered pussy and legs as she stood about 10 feet away. "Hmmm. Nice, come closer," the man requested. Karen knew she must comply and took a step towards him and stopped. "Closer," he demanded. She moved until she was now just a few feet in front of him. He was sitting with his face just below the crotch area of her panties.

Karen was now shivering. Unsure if she was turned on, cold, or scared. "Spread those legs," the man grunted in a voice that sounded as if he was a heavy smoker. Karen could now smell the man and the odor burned her nose. He obviously was intoxicated and had not bathed in some time. She did as she was told and parted her legs. She could feel her lips part as her legs widened and the thin gusset of her thong slid between her labia, soaking up the moisture.

The man leaned forward and Karen was too scared to move. His nose stopped an inch from her exposed pussy and he inhaled deeply. Karen just stood there, knowing the man could smell how turned on she was. She never realized that fear could elicit much the same arousal response in her. As the man continued to smell her pussy he fumbled with the zipper of his trousers.

"Turn around and bend over," the man commanded. Karen was worried. Turning would mean she could no longer see the man and bending over would expose her pussy and ass to this man that was now pulling a sizable, flaccid penis from his pants. Would he try to fuck her? He hadn't done anything thus far that would allow her to say no so she took the risk and turned.

As she turned, now facing the other side of the street she wondered if Nancy or anyone else could see her. Her thoughts were dashed as the man ordered her to bend over. She did and as she did her bottom was forced backwards right into the old man's face. His tongue extended and slid into her moist folds. She could feel his nose resting against her rosebud. She quivered in a mini orgasm.

"Oh, God!" she thought, "he is licking my pussy," but suddenly the man's face fell away from her backside and she felt a rush of air. She looked back between her legs and noticed the man had fallen backwards, passing out from his intoxication, his limp cock still hanging from fly.

On the one hand, Karen was happy things were over with this man. On the other she couldn't believe how good he had made her feel in his brief licking. She straightened and pulled the coat together to cover herself. Looking down at the man, she knew she couldn't leave him like this. If anyone saw him with his cock out, he would get in trouble. She didn't want to be responsible for that. She knelt next to him, reaching for his penis. As her fingers circled his penis it was as if an electric jolt had shocked her body. She gave his penis a slow tug, up and down and felt it get slightly larger. She looked at the man's face, now seeing he was her father's age, and knelt lower bringing her face down. "Well, I've already done things I never thought I'd do, might as well" she thought. She could definitely smell the musky scent coming from his groin but she couldn't stop herself from licking the shaft and circling his head with her mouth. She sucked gently on the first cock she had ever permitted herself to suckle. She could taste the clear liquid that had seeped from his head. Giving the man two more tugs, she removed her mouth and inserted his cock into his pants. She left him unzipped but he was no longer exposed.

Crossing the street, she continued down the next block. Her legs were visibly shaking and her breathing was ragged. She wondered if she would make it the remaining distance. She couldn't believe what she had done. What had come over her to take a stranger's cock into her mouth, something she hadn't even been willing to do with boyfriends? Nancy was rubbing off on her. Was she turning into a slut?

She continued walking down the second block. To her surprise there was no one and she started to regain her previous self. She could still feel that her nipples were hard and the wetness between her legs but her breathing was back to normal.

As she crossed to the third block she saw a group of college age young men at the far end of the block. He knew there was a college in the area and many students had apartments in the area. She slowed her walk, hoping they would go into a building. They continued bouncing a basketball on the far corner of the block.

Karen was now moving as slowly as she could. She was unsure about exposing herself to this group of young men. They were all obviously in their early 20s, but they were much younger than her and there were 6 of them. These young men weren't going anywhere she realized. She slowly advanced towards them and they stopped bouncing the ball and looked at her. Karen could see there were two black men and four white, she halted and slowly undid her coat. She flashed them her body, turning once, before stopping right in front of them.

She could plainly see the cocks hardening in the shorts the boys were wearing. The boys began making nasty comments. "Mmmm, whore, we will fill all your holes." "You'd like that wouldn't you." "Look at the way that thong is wedged in her cunt."

Karen had never heard things like this said about her before. She quickly pulled the coat closed and moved along down the street. Technically she hadn't broken any rule as they hadn't asked her to do anything.

Karen, now fearing that the group might come after her, hurried down the fourth block. She was hopeful of not running into anyone else, getting through this dare and back to the safety of her own home. She had already done things she never thought she'd do. She'd exposed herself to complete strangers. Had a homeless man's tongue in her pussy and his cock in her mouth. Had a group of young men tell her things they wanted to do to her.

She had nearly traversed the fourth block when a young couple, about her age, exited a building. "Damn," she thought. I was almost there. "Why couldn't they have stayed inside another five minutes?"

The couple looked at Karen as she walked towards them. She looked completely out of place in this neighborhood dressed like she was. As the couple smiled at her, Karen undid her coat and flashed her body at them. "Holy shit!" exclaimed the young woman, as her boyfriend stared, his mouth wide open. All three of them stopped, mere feet from one another.

"God, you look amazing," said the man.

"You really think so?" Karen asked.

"Yes!" both the man and woman replied.

Karen blushed and looked them both over. She could see wedding bands on their fingers.

"You should probably be careful dressed like that in this neighborhood," the man explained.

"Why are you dressed like that? And why are you showing your body to us?" the woman asked.

'It is a long story." Karen replied.

"We've got all night, as long as I get to continue to look at you," the man said.

Karen blushed again. "I would be happy to tell you, but I don't feel comfortable doing it here."

"Our place is right here, if you feel comfortable going inside with us," the woman responded.

Karen thought they looked normal. "Am I really considering going into some strangers' apartment and letting them look at me? All of me?" she thought. She nodded, "Ok" and she followed them up the steps and inside.

Once inside the couple offered Karen a drink. So many thoughts were running through Karen's mind. "What if they drug me? What if they lock me away in a room and keep me as a slave? You hear about those things," she said inside her head. In the end they offered her a beer or a White Claw, both in unopened containers, so she accepted the White Claw.

The couple introduced themselves as Jay and Christine and sat on the love seat. They said they had only lived here a few months and had been married less than a year. Karen stood in front of them both, took a sip of her drink, set it down on a coaster and removed her coat. She stood in front of them in bra, panties, garter and stockings, exposing herself to them as she knew Nancy would expect. Christine's hand dropped to her lap, pushing on her pelvic area and Jay shifted in his seat.

"I'm dressed like this on a dare. The dare was I had to expose myself to anyone that I came across on a four block walk. My walk was just about to end, when you came out your door. I just had to turn down the alley where my friend is waiting. She is the one that dared me." Karen told them.

"Why did she dare you?" Jay asked.

"Because I'm a bit of a prude and she felt this would get me out of my shell. It has." Karen responded. "Oh, I almost forgot. I have to show whatever they ask to see. I can only refuse, if I want, if they ask me to do something."

"Show us the pussy," Christine blurted, barely realizing what she had said. Karen pulled the thong to the side revealing her shaved labia to them both. "You look wet," Christine told her.

"I am." Karen blushed.

"Show us how wet." Jay demanded. "Stick a finger in yourself and let us see."

"That is hard with my thong on," Karen replied and Christine told her to take it off them.

With nerves racing, Karen dropped her panties to the floor. "Will you throw them to us?" Christine asked. Karen did and Christine caught them. While Karen stood in front of them, legs spread, finger tracing the lips of her pussy, Christine brought the panties to her nose, inhaled deeply and then handed them to Jay, who did the same. As one and then two fingers sank into Karen's creamy wetness, she moaned and removed her fingers. They were both coated and as she spread the two fingers, they were connected by the sinewy juice.

"Have you ever tasted yourself?" Jay asked. Karen shook her head, no and he told her to do it. She wasn't sure where this fell in terms of her being able to refuse or not. Technically, they were asking to see something. They weren't doing anything to her. She raised her fingers to her mouth and tasted herself for the first time.

Now it was Christine and Jay's turn to moan. Turn and spread your sexy ass cheeks, Jay told Karen. As she did, Christine asked Karen if she minded if they got naked as well. Karen thought she might feel better if they were naked too and agreed. Her hands reached back and spread her cheeks, exposing her tight rosebud to them.

She was shocked when she looked back over her shoulder to find them both naked. "How could they have undressed so quickly," she thought. Jay's cock was as big as any she had ever seen and he was quite muscular. Christine had a perky body. Her breast were a nice size, capped with hard nipples, and her pussy was shaved completely bald.

"May I touch your nipples?" Christine asked. Karen responded she could and Christine got off the loveseat and came around the other side of Karen. As Karen held her cheeks open for Jay to observe, Christine tweaked Karen's nipples before lowering her mouth to them. "Sucking is different than touching," Karen thought but she didn't stop her. Christine bit down on one nipple, giving Karen a jolt.

"Would you like to touch Christine's nipples, maybe suck them?" Jay asked Karen.

"Oh, yes, please do." Christine echoed.

Karen had never done anything like this. Hell, before this night she had only had intercourse. Now she had done much more. "Why not," she said and brought her hand to one of Christine's hard nipples and her mouth to the other. She bit down on the nipple as Christine had bit hers, causing a loud moan.

Karen felt Jay's hand touching her ass. "Hey, he didn't ask," she thought but she didn't stop him. She felt his tongue licking her ass, down her crack. "You can use your tongue, but I don't want to fuck. OK?" she told him. She couldn't hear his response, only feel it, as his mouth was on her bottom, licking between her cheeks.