Leslie was 38, but she didn’t look a day over 30. A very petite brunette, she stood 5’2” and weighed just 110 pounds. She had enhanced breasts (a gift to herself after her first divorce) that perfectly filled out her 34C bra. She never had kids and worked out regularly to keep the aging process at bay. Leslie had some wonderfully feminine features. Thick, shiny, black hair that came down just past her shoulders. Soft, full lips and large blue eyes that had the ability to somewhat distract passers by from her small ass. She had one of those backsides that seemed to defy gravity.
The week-long business trip Leslie had just begun was a welcome distraction. She couldn’t believe she was finalizing the end to her second marriage. “How could this have happened again?” she kept asking herself.
But, at least for the next few days, she had a change of scenery and the chance to catch up with an old friend. Leslie got to visit San Diego twice per year as a Regional Sales Director for a global rental car company. One of her very best friends from high school lived in Southern California and the two rarely missed an opportunity to see one another when they could.
The hotel where Leslie was staying had a great steak house in the lobby. She was at the restaurant bar when Jen walked in just past 8:00pm.
Both women were dressed in business attire. Black skirts that ended just above the knee and tailored jackets. Jen work a pink silk scarf around her neck.
Jen looked more like a prototypical 38 year old woman. Still very attractive, her eyes were starting to show a few wrinkles and her hips had widened, slightly since the birth of her two children. She had natural 34A breasts that were beginning to lose the flight with gravity. However, she still had very toned legs and arms and her natural confidence was always evident on her face.
The two women hugged and sat down. Leslie got the bartender’s attention, pointing to her wine glass and then to Jen.
The look of pity on Jen’s face was already showing. “Don’t give me that look,” Leslie scolded. “I’m fine. Really. This marriage didn’t work either and I’m at peace with it.”
“But what happened?” Jen asked. “You never said you two were having problems.”
“This one was my fault,” Leslie admitted. “I’m sure that’s not true,” Jen consoled.
“I don’t quite know what happened,” Leslie started. “I was at a convention and this guy I’ve known for about a year was there. We had a few drinks. I ended up in his hotel room. And…you know… That was it.”
Jen shook her head and smiled. “You just can’t control yourself, can you?”
“With this guy, I really couldn’t,” Leslie admitted. “He smiled at me and I soaked my panties. Maybe there’s something wrong with me.”
“There’s nothing wrong with you,” Jen assured her grabbing the wine glass that had been placed in front her. She rose the glass in the air, smiled a huge grin and commented, “You’re just a slut.”
“Just because I enjoy sex does not make me a slut,” Leslie said defending herself. “Well, maybe a little. Things started out great in bed with Dan. But after a while we would do the same things and find ourselves in the same positions. It became boring and he wasn’t willing to try anything new,” she added.
“What suggestions did have for him?” Jen asked.
“I didn’t think I was suggesting anything TOO out there,” Leslie started. “I offered to be tied up. He didn’t want to do that. He said ‘It would be weird to see you so helpless.’ I offered sex outside, in the car, and in a bathroom at a restaurant. Dan felt the risk of getting caught was too high. I finally got him to try the bathroom when we were out one night but he couldn’t get hard. He said he was too distracted.”
“And you know me,” Leslie continued. “I have to have a fulfilling sex life.”
“Ah. Yeah,” Jen said knowingly. I don’t even want to count the number of boyfriends you scared off over the years because you need to get laid so often.”
“I don’t need to get laid very often,” Leslie said. “Every other day is fine with me. And I just need a little variety.”
“Every other day?” Jen moaned. “I’m lucky if Jake and I get to have sex once per WEEK.”
Just then, a young hostess approached the two women. “You’re table is ready ma’am,” she said to Leslie. “Are you ready?”
“Yes. We are,” the women said together grabbing their wine glasses.
“Please follow me,” responded the hostess leading them away from the bar.
The hostess stopped toward the back of the restaurant at a plush booth and held out her hand. Leslie and Jen sat down across from each other.
“We’re going to need two more of these,” Jen said pointing to her near empty glass.
“Once per week would not cut it for me,” Leslie said picking up the conversation where it had left off at the bar. “I think you know I need more than that.”
Leslie and Jen ordered dinner and talked about friends, family and the usual topics that come up when you get a chance to talk with an old friend.
As the wine kept flowing, the two women were becoming increasingly intoxicated.
Over dessert, Jen asked, “Do you remember, in college, when we used to dare each other to do things?”
“I remember,” Leslie smiled.
“I could never get you to back down from a dare,” Jen admitted.
“That’s because all your dares were so ‘vanilla,’” Leslie teased. “They were things like, ‘Go to class without panties’ or ‘give a guy a blow job before the end of the day.’”
“Well those weren’t ‘vanilla’ to me,” Jen noted. “Obviously, I was much more reserved than you.”
“I think my favorite was the one that wasn’t so plain. You dared me to have sex with three different guys within 24 hours,” Leslie remembered fondly. “As I was getting fucked by that third guy, I remember thinking, ‘he has no idea what I’ve been up to today.’”
“So is there a fantasy you haven’t accomplished yet?” Jen asked.
“Well sure,” Leslie started. “You always have to have goals, right? You need to keep pushing the limits. That’s what makes life fun.”
“Well, we’re pushing the limits for me tonight already,” Jen said. “I’m awake past 10:00,” she said smiling and taking the first drink of her fourth glass of wine.
After a moment of awkward silence, Jen began to speak. “So, what’s the fantasy you haven’t fulfilled yet?”
“You nosey bitch,” Leslie scolded. “You’re trying to live vicariously through me.”
“Of course I am,” Jen answered. “I’ve been married for 9 years. I have two kids. I need your stories.”
“You’re pathetic,” Leslie said to her friend smiling. “But, I’ll indulge you because you were a great friend for rearranging your schedule so we could have dinner together tonight.”
Leslie started to describe her fantasy as Jen leaned in attentively. “Lately, I’ve been thinking about what it would be like to fuck a guy that I have never met before. But also, he never says a word to me. When we’re finished, we get dressed and it’s over. I leave without knowing his name. I leave without knowing what his voice sounds like. Our only communication is with body language and eye contact.”
“Well, it’s official,” Jen said. “You are a Grade A nymphomaniac. Is that even possible?”
“It has to be possible,” Leslie answered. “I’m sure it’s been done.”
“So how are you going to accomplish this one?” Jen asked.
“I’m not sure. It’s not like I can just go out on the street, make eye contact with a guy and have him read my mind.” Leslie said realizing how difficult this fantasy might be to fulfill. She never backed down from a challenge and found the pursuit of her various fantasies almost as enjoyable as the sex itself.
Over the years, Leslie had accomplished every sexual fantasy she had. Mile High Club. Check. Two men at once. Check. She had even had sex while scuba diving. It was a bit awkward, but at least she could say she had done it.
As she was describing her fantasy to her best friend, Leslie realized she was becoming extremely wet. Talking about this out loud had caused her to recognize that she really did want this dream to come true.
“Leslie.” Jen said trying to get her friend’s attention. “Leslie!” she said again louder.
“What? Oh, right. What were we talking about?” Leslie stammered. She had been staring blankly into the last remaining crumbs of her carrot cake.
“We were talking about you pursuing another fantasy,” Jen said rolling her eyes. “I guess you got a little lost in thought there.”
“I guess I did,” Leslie admitted. “Well, it looks like my travel vibrator will get a work out tonight.”
Jen shook her head. “When I get home, I’m sure there will be a sink full of dirty dishes. I hope you enjoy your orgasm…or orgasms,” she said.
Leslie motioned for the server to bring their bill. “This has been fun,” Jen said. “I’m glad we got to meet up again. Let me know the next time you’re in town.”
“Of course I will,” Leslie assured her.
The server came over with the check, but there was a note on top of the bill. “What’s this?” Leslie asked.
“I’m not allowed the say,” the server said.
Leslie looked down and read the note. Her eyes widened and her jaw dropped. “What does it say?” Jen asked impatiently.
Leslie motioned for the server to leave their table and handed the card to her friend. Jen read the hand written note out loud. “I was sitting in the booth behind you. I heard your fantasy. Room 1275 tonight if you want to make it happen. I’m only here for one night.”
Both women were stunned. Neither could talk. “He obviously heard everything,” Jen finally managed to say. “I don’t know if you should be turned on or disgusted.”
“It’s a little creepy,” Leslie acknowledged. “But it’s also kind of hot.”
“Oh you are so fucked,” Jen told her. “You have that look in your eye. I know that look. You can act all innocent and shocked now, but you are going to let this guy fuck your brains out.”
“Do you remember what he looked like?” Leslie interrupted.
“I don’t,” Jen admitted. “I wasn’t paying attention to anyone around us.”
“You know me so well,” Leslie said. “This is REALLY hot. Do you know how wet I am right now?”
“Ok. Go do your thing.” Jen said shaking her head. “Just be safe and I want details tomorrow.”
The women hugged each other once more and Jen walked out of the restaurant. Leslie sat back down and tried to figure out the correct tip. Her mind was racing and, after three attempts, she told herself, “Settle the bill first. Then I’ll figure out what to do.” She wrote her room number on the check and headed out of the restaurant, not sure of what she was going to do next.
Once in her room, Leslie headed straight for the bathroom. She reached down and pulled up her skirt to expose the small dark green triangle of her silk thong. It was completely soaked. Leslie decided to wriggle out of them. She held them up noticing the entire front area was wet.
She pushed her skirt back down. “I’m going to fuck him anyway,” she thought to herself. “Why even wear panties?”
After quickly brushing her teeth and touching up her makeup and hair, Leslie took a deep breath. She hung her jacket in the closet and headed out of her room wearing the same black skirt, white blouse, and black sheer thigh high stockings she was wearing at dinner.
Leslie approached the elevator and nervously touched the “up” button. When the elevator car arrived she was thankful it was empty. She quickly moved in and pressed the “12” button. Coming from the 4th floor, the ride seemed to take quite a long time. At the 12th floor, there was a “ding” and the doors opened. Leslie stepped off and looked to see which direction she needed to go to find 1275.
There was a placard on the wall in front of her. She looked quickly at it and said to herself, “Left.”
Walking down the long hallway, she wondered if she would see anyone else. 1255, 1257, 1259… Leslie knew she was getting closer and her heart was pounding so hard she could hear it in her chest. As she got to the end of the 1260’s, her legs were becoming weak. Finally, she was standing in front of a door that had “1275” on it.
Leslie took a deep breath and looked around to see if anyone was near her. She composed herself and thought, “This is a fantasy about to come true. Get it together.”
She raised her hand, clinched it into a fist and gave two firm knocks in the middle of the door. Leslie could hear someone approaching from the other side.
“What is this guy going to look like?” She thought to herself. “What if he’s hideous?” For a minute she thought about running back toward the elevators. But before she could, the lock released and the door swung open.
Standing before her was a man who Leslie thought to be about 35. He looked to be about six feet tall and had brown eyes and short brown hair. The man was wearing jeans with an un-tucked orange button down shirt that had the collar open. Leslie’s best guess on weight was 180 pounds.
“Hi. Hi…I’m Les…” Leslie started to say before being interrupted. The man raised his hand stuck his index finger out, covering Leslie’s mouth. He brought the finger back to his mouth and pressed it against his closed lips. Then the pulled the door back and gestured for Leslie to come into the room.
Once inside, he closed the door. Leslie stared at the room taking in the surroundings. The king bed in the middle of the room looked as if it had not been touched since housekeeping made it earlier in the day. There was a suitcase on the floor next to the t.v. and it was closed. A few suits hung in the open closet next to her.
Leslie turned to face the man behind her. As soon as she did, he grabbed her around the waist and drew her closer to him. Then he leaned in and kissed her. The two embraced in a long passionate kiss and they made their way over to the bed.
The man nudged Leslie and she sat on the edge of the bed. He began to unbutton his shirt as she watched in anticipation of what she was going to see. Before he shed his shirt, he motioned for Leslie to unbutton her blouse. Instinctively, she began to comply.
The man took off his shirt and revealed his trim upper body. He wasn’t sculpted like a professional athlete, but he looked very healthy. His stomach was flat and he didn’t have any hair on his chest.
Leslie got her blouse off revealing her white lace bra. The man reached out his hand and guided Leslie to her feet. He reached back and unhooked her bra in one motion and then peeled the straps off her shoulders, revealing her perfect breasts.
The two began to kiss again. Leslie loved the way this man felt against her. He was warm and he was in control. The man reached down and put his hand on the back of Leslie’s thigh. As they were kissing, he ran his hand up her leg and realized she wasn’t wearing any panties.
Leslie could feel his cock getting harder in that moment. The man broke the embrace and raised his eyebrows at her. She gave an innocent look, shrugged her shoulders and smiled.
Before Leslie knew what was happening, the man grabbed her around the waist and lifted her into the air. He dropped her on the bed, face down, and went right for her skirt. He found the half zipper on the back and loosened it. Then, quickly, he grabbed Leslie’s hips and turned her onto her back.
From here, the man could see Leslie’s gorgeous pussy. He tugged at the waistline of the skirt and Leslie raised her hips off the bed to allow the man to remove the clothing. He knelt between her legs and pushed her knees further apart. The man started down at Leslie’s slim pussy lips. She had a small triangle shaved into her jet black pubic hair. She had shaved everything else smooth just that morning.
Leslie’s inner lips protruded, slightly, and the whole area was glistening wet. The man set one finger on her clit and lightly ran it down the middle of her swollen pussy. At the bottom, he inserted his index finger and Leslie moaned. He pulled it out and started to make a circle around her clit. Her legs shook a little with the pure pleasure she was experiencing.
The man massaged her clit for another minute before lying on his stomach. His face was now just inches away from Leslie’s pussy and he could see the juices running out of her. He placed his middle and index finger just inside her lips and spread them apart. For a second he just stared at the beautiful pink slit in front of him. Leslie’s hips raised in anticipation.
The man was not going to tease her. He stuck out his broad tongue and began to lick Leslie from the bottom of her pussy to the top.
“Oh yeah!” she screamed as his mouth worked her over. She started to writhe so much the man had to put his hand around Leslie’s hips and push her into the bed as he was going down on her.
While holding her down, he took her clit in his mouth and began to suck firmly on it.
“That’s it! Just like that!” Leslie moaned. “I’m close. Don’t stop.”
Leslie loved the light resistance of the man keeping her pinned to the bed along with his talented tongue. The man kept working Leslie’s clit and, as promised, her pussy began to spasm.
“Yes! Yes! Yes! Ahhhhhh Yes!” she moaned. Her whole body was shaking as the man continued to suck on her clit, bringing her all the way through the powerful orgasm.
As her body began to relax, the man disengaged his mouth. Leslie’s juices were running down his chin. He slowly slid himself off the back of the bed and walked around toward Leslie.
He was now standing at the side of the bed and she was lying on her back still recovering from what had just happened. He stood next to her, looking down at her wonderful body. After collecting her thoughts, Leslie worked her way over to the man who had just performed so well with his mouth.
He didn’t know it, but this was one of Leslie’s favorite parts of having sex with someone new. She loved the moment just before a new cock was revealed to her. What would it look like? Would it be long? Thick? Does he keep himself trimmed?
Leslie was now on her stomach looking up at the man. She grabbed the waistband of his jeans and released the button. She slid the denim down over his hips revealing royal blue boxer shorts. His cock was already pushing the fabric out and Leslie could tell he was not small.
She hooked her fingers around the waistband and pulled the elastic out toward her, pushing the boxers down in one motion. Leslie was face to face with what she estimated to be an eight inch cock. It wasn’t the biggest one she had ever had inside her, but it was close. He had also shaved recently. His balls did not have any hair on them he had trimmed the rest very short.
The man’s cock was also relatively thick. Leslie put out her hand and wrapped it around the rock hard staff. She had a small hand, but the tip of her thumb could barley touch the tip of her index finger has she held the man in her hands.
Leslie stuck out her small pointed tongue and placed the tip of the cock on it. She used her tongue to circle the tip for a few seconds and taste him. Leslie like the way he tasted. There were already a few drops of precum beginning to exit his body.
Leslie took his cock into her mouth further. She had about four inches in her mouth and she started to lightly rub her finger tips over his balls with her free hand. The man moaned and Leslie realized that was the first sound she had heard him make.
Leslie pulled her mouth off his cock and turned onto her back. Her head was now hanging off the edge of the bed and she was staring up at him. She spread her legs and reached for his manhood with an open mouth. He brought it down to her, entering her warm mouth.
Around the age of 25, Leslie discovered she could deep throat most cocks in this position. With her head back, her throat was open and accommodating.
The man soon realized how deep she could take him. He slowly kept pushing downward and Leslie showed no resistance. He pulled back for just a second before pushing his whole cock into Leslie’s mouth. He held her head and moaned again. Leslie knew she was pleasing him. She could feel the tip of his cock deep in her neck.
The man pulled back and Leslie inhaled a deep breath. His cock was covered with her saliva and she loved the way it looked, dripping off of it. The man grabbed himself and put the tip of his cock over Leslie’s mouth. She opened and he immediately plunged himself downward again.
As she was taking the man down her throat, he leaned forward and braced himself on the bed with his left hand. He inserted his middle finger of his right hand into Leslie’s open pussy and he could feel her moan around him with her full mouth.
Again he circled her clit and Leslie let out a high pitched muffled squeal. The two were almost in the “69” position as the man was thrusting his hips.
“I’m not blowing him,” Leslie thought. “He’s fucking my mouth.”
As she was concentrating on what he was doing to her mouth, Leslie didn’t realize that another orgasm had quickly built inside her. Her legs began to shake again and the man knew what was coming next. He found the exact right spot on her clit and didn’t move his finger off of it.
Leslie moaned around the cock that was penetrating her throat. She began to cum once again. This was too much for the man to take. As Leslie began to spasm, the man started to dump load after load of hot cum down her throat.
Leslie had made a point, over the years, to only swallow guys that she was in a relationship with. In this case, however, she didn’t have much of a choice. She felt he was so far down her throat that he was almost dumping he load directly into her stomach.
She was cumming and he was cumming at the same time. Leslie’s mind went blank. She couldn’t keep a thought for more than a second.
Then, he slowly pulled out of her mouth and gave her clit one last flick. Leslie jumped at the sudden sensation. She turned over on to her stomach and pushed herself back on the bed so her head was supported.
The man held up one finger as if to say, “wait.” He went into the bathroom for just a minute. When he came out, he was holding two cold bottles of water and two towels. He handed one of each to Leslie. She took them both, stealing a glance at his now only semi-hard cock.
She cracked open the bottle and began to drink quickly. She didn’t realize how thirsty she had become. The man drank his water too as his breathing was starting to slow. Leslie felt like silence was become awkward. After all, they were both naked and not saying anything.
“So,” Leslie started. “When did you start eavesdropping on my conversation it the restaurant?”
The man just smiled at her but didn’t say anything. After a few seconds of silence, Leslie said, “Of course. Part of the fantasy is to not hear you speak.”
The man smiled again and reached for her now empty bottle of water. She gave it to him and he disappeared into the bathroom once again.
After a few long minutes, he emerged with a towel in his hand. He man placed it across one of the hotel chairs and sat down. He motioned for Leslie to come join him. She got up from the bed and walked over to the man. He patted his upper leg and she sat down.
As soon as Leslie was on his lap, he reached down and began to run his fingers over her pussy lips. She reached down and grabbed his cock which was starting to show signs of getting hard again. “Wow!” Leslie thought. “It’s only been 10 minutes.”
The man parted her pussy lips with two fingers and pushed them into her. He found Leslie’s G spot and began to massage it with his middle finger. As Leslie let out a soft moan, the man was almost fully erect again. He began to rub his left hand on Leslie’s chest. His hands were running over her soft but firm breasts.
Leslie had begun to gush juices again. It had been a long time since anyone had made her this wet. This guy really knew how to use his hands. Just then, the man stood up and guided Leslie to her feet. Her back was to him and he guided her toward the bed. She could feel his cock in the small of her back.
When they got to the bed, the man put his hands under Leslie’s arms and picked her up. He playfully tossed her onto the bed. Leslie was on her stomach after being thrown on the bed and the man quickly moved in behind her. He positioned himself between her legs and she was now on all fours in front of him.
The man paused just a second to take in the beauty that was in front of him. Leslie had such a small ass and it was now pushed up toward him, leaving her bald, wet pussy vulnerable to him.
Leslie was getting a little nervous about the size of the man’s cock. She turned around and said, “Go slow at first.” The man nodded.
He placed the tip of his cock against her lips. He ran it up and down just penetrating the smooth folds and getting the end wet. Then, with each thumb, he spread Leslie’s pussy and inserted the first three inches of his hard cock.
Leslie rolled her eyes with pleasure and let out a moan. When he felt she had adjusted, he pushed in another three inches. Leslie’s hand instinctively reached back to stop him from pushing any more in. She took a few breaths and placed her hand back down on the bed.
The man then pushed the rest of himself into Leslie. “Oh yeah,” Leslie moaned. The man held himself completely inside her as Leslie’s most intimate muscles stretched to accommodate him.
He slowly pulled back and looked down to see his cock glistening with her juices. Just before the tip was removed he plunged himself all the way into her again. Leslie began to thrust her hips back to match the man as he was entering her. “Oh that’s so good,” Leslie said in the throes of ecstasy.
Leslie reached between her legs and cupped the man’s balls as he was fucking her. He let out a deep moan and Leslie knew what she was doing. She turned her head back to see the pleasurable expression on his face.
Not wanting to cum just yet, the man pulled out of Leslie and gently pushed her to the side. He lay down on the bed on his back. Without any guidance, Leslie got up and stood over him with her back to his face. She lowered her tiny ass down, reached between her legs and grabbed the cock. Leslie placed the tip at her wet opening and sat down on the man taking all of him into her.
Leslie was grinding her hips down into her new lover and he placed his hands around her waist. He pushed her down as hard as he could and he could tell this wasn’t going to last much longer. Leslie knew exactly what she was doing and she was a wild animal. She closed her eyes and concentrated on massive cock inside her. She felt so full and stretched, but it was exactly what she needed.
Quickly, an orgasm was building inside Leslie. The feelings were coming so quickly and she started to lose control. In a matter of seconds, Leslie was cumming again.
The man groaned as he saw Leslie enjoying her third climax of the night. She knew he was going to cum soon as well. She quickly pulled herself off of him and thrust her legs back. She was lying on top of him with her pussy next to his face. She took his cock into her mouth and massaged his balls. After just a few seconds, the man tensed and he began to shoot another load into Leslie’s mouth. This time, Leslie didn’t give a second thought to swallowing him. He tasted so good and had gotten her off three times this evening. She kept sucking his cock until every last drop of him was inside her.
Leslie collapsed on top of the man with her head on his leg just inches away from his now softening cock. Neither of them wanted to move for a few minutes. When they collected their breaths, the man stuck out his tongue and gave her sweet pussy one quick lick before lifting her off of him.
The man got up off the bed and collected Leslie’s clothes. He set them on the bed next to her and headed into the bathroom. Leslie began to slowly get dressed. She was now realizing how exhausted she actually was.
When the man came out of the bathroom, Leslie was adjusting her skirt and looking in the mirror. She knew there was no way to make it look like she had not just been fucked. Her hair was a mess. Her cheeks were flushed and she couldn’t keep a perpetual grin off her face.
The man nodded at her and smiled. The he walked her to the door and opened it, ushering her out into the hallway.
Leslie didn’t quite know what to do. This man was kicking her out. Not even an offer to spend the night. As she turned away and started to walk down the hall, she realized that was EXACTLY what she wanted. She had fucked this stranger and not heard him utter a word.
Leslie quickly made her way back to her room, hoping nobody see her in her freshly fucked state.