Peeping Tim

Tim was an 18-year old high school student nearing graduation. Tim was tall and athletic, but a shy kid. He had lived next door to Sadie and her family his entire life. Tim and Sadie's parents were good friends and often went out to dinner and had parties together. Any time one family had a party or event, the family next door was invited. Which also meant that most times Tim and Sadie got drug along to the event with their parents. The families occasionally even took vacations together.

Sadie was 24-years old and had recently moved back home to stay with her parents. She was taking some time off before attending graduate school in the Fall. Sadie was very attractive. She had blonde hair and a petite frame with nice legs and a perfect, firm, round butt. She also had a very nice set of boobs. Sadie was well put together. From the moment Tim had become interested in girls, he had always thought Sadie was gorgeous.

Sadie was always friendly toward Tim. Because their families were close, Tim and Sadie had spent a decent amount of time together growing up. When they were younger, Sadie even babysat Tim a number of times. Because of their age difference, they weren't close friends, but they occasionally hung out together without their parents and always got along well when they were together.

Most people knew Sadie as a sweet, innocent girl. She wasn't a conservative prude, but no one knew her as a wild child either. She got along great with her parents and never really got into trouble. Sadie did, however, have an adventurous side most people did not know.

Tim and Sadie's parents' houses were typical tract homes with not a lot of space between them. Tim and Sadie's rooms were both upstairs and faced each other. The other bedrooms in the houses were on the opposite sides of the houses. So, the only real view into Sadie's room from outside was from Tim's room, and vice versa.

One evening Tim was at his desk in his room surfing the internet. The light switched on in Sadie's room and caught his attention. Tim turned and looked. Sadie's drapes were open, and he saw Sadie enter her room. Sadie proceeded to get undressed, stripping down to her bra and skimpy thong panties. She laid face down on the bed and opened her laptop.

Tim continued to watch Sadie, but he did not want to get caught staring. So, he quickly turned the lights off in his room. He continued sitting in the dark watching her. Tim had seen Sadie in a bathing suit bikini before, but nothing ever this revealing. And the fact it wasn't her bathing suit, but rather her bra and panties which were not meant for public viewing, excited Tim. Tim continued watching her intently for 30 minutes. Eventually, Sadie closed her laptop. She went to the window and closed her drapes.

The lights then went out in her room. Tim was very excited about what he had seen. Tim hadn't dated a lot, so seeing a beautiful woman in her panties in person was exhilarating.

The next evening, at about the same time as the previous evening, Tim looked out his window. And, at about the same time, Sadie entered her room and repeated the same routine from the night before. Tim quickly turned off his lights when Sadie entered her room. Tim again watched Sadie from the darkness. This routine repeated almost nightly as Sadie routinely went to bed at nearly the same time.

Tim started watching out his window in the daytime to see if he could catch a glimpse of Sadie from in-between a small slit in the middle of his nearly closed drapes. On numerous occasions, he got a glimpse of Sadie changing or laying around in her panties.

On a few occasions, Tim thought Sadie might have seen him. When he did, he quickly closed his drapes or turned out his lights. Since Sadie didn't change her actions and still exposed herself, Tim assumed he hadn't been caught.

One afternoon, Sadie walked by her window in her panties and noticed the curtains moving in Tim's room. He had just tugged them closed hoping she didn't see him. The next night she caught a brief glimpse of Tim dashing across his room to turn off his lights when she entered her room. She didn't take any action to indicate she caught Tim peeping on her, but she had figured out he was. Sadie actually kind of liked having a secret admirer next door. She knew Tim was harmless and his interest in her was a tiny confidence booster for Sadie.

Once Sadie discovered Tim was watching her, she decided to have fun with it. Since she did not mind Tim seeing her, she intentionally gave Tim a tiny show from time to time. Sadie started being more deliberate about giving Tim a look, but not so obvious that he would know she was on to him. She occasionally would walk to the window topless to close or open her drapes to give Tim a good view. Sadie enjoyed it. She figured what 18-year old boy, including Tim, wouldn't want to see her beautiful body? She thought it was harmless fun teasing Tim a little.

Sadie almost always knew when Tim was watching her, as she could see a faint glow from his laptop in the corner of Tim's room with the rest of his room lights off. She rarely actually saw Tim in his room, but she kind of knew when he was there. She knew his parents didn't allow Tim to go out on school nights, so she definitely knew he was home every school night even though his room was typically dark and she couldn't see in.

Sadie often laid out in her back yard to get a tan. Her yard was secluded from view from most of the neighbors with hedges and tall trees between the yards. You could however get a view of a portion of Sadie's back yard at a distance from Tim's room. Sadie purposefully placed her lounge chair where it would be in view of Tim's room. When her parents were not around, Sadie often laid out topless in a position Tim would be able to see her, or would get up without her top on and walk inside to retrieve a drink.

Tim's parents owned a boutique women's clothing store downtown. They mostly catered to women in their 20s up to about 35. The clothing was too expensive for high school students, and too trendy for anyone over 35. Sadie shopped there often. She liked the clothes and Tim's parents sold them to her at cost, so it was a great deal for her.

Tim's parents made him work at the clothing shop, mostly on the weekends. They insisted he did so to learn work ethic and responsibility. He got paid normal wages, but Tim hated working there. It was the least cool job for a high school kid he could imagine. Attractive women often frequented the store, but they were substantially older than Tim. And their age didn't matter, because Tim was too shy to flirt with anyone that came in the store. So, Tim really saw zero upside to working there.

Sadie always had Tim help her when she came to the clothing store. She preferred interacting with someone she knew, and he knew about her discount, so it made it easier than working with any of the other employees. Since the store was small, it was common that Tim was the only one working there when Sadie visited. Sadie knew the times when the store typically wasn't crowded, so she often shopped there then.

After Sadie had discovered that Tim was peeping her, she decided to extend her teasing fun to the store. The doors of the dressing rooms were half-sized, so they were open at the top and the bottom. They came within a foot of the floor and were almost seven feet tall from the floor to the gap at the top, so no one could see in when they were closed. Sadie had frequently asked Tim to get her other sizes of clothes she was trying on in the dressing room. He would fetch what she asked for and then drape it over the top of her door.

But now, Sadie started leaving her dressing room door cracked partly open as she was changing when no one else was in the store. When she did this, you could get a slight glimpse inside the dressing room as you walked toward it. She often would wear a sexy thong or V-string to the store and would purposefully strip down to her panties and call out to Tim to grab her another size. She turned her back toward the door as Tim approached.

This gave Tim a brief glimpse of her tight ass, but also gave him the impression she didn't know he could see since her back was turned to him and the door. Sadie could see in the mirror and through the crack in the door Tim approach her dressing room behind her, but he never noticed that. She confirmed Tim was in fact peeking at her. Sadie enjoyed being a little exhibitionist in this manner.

Occasionally, Sadie got bolder teasing Tim at the store. When no one was around, if she was wearing more of a bikini style set of panties, she would come out of the dressing room wearing a sweater or blouse and no bottoms, revealing the lower half of her panties. She would ask Tim to get her another size or go get one herself off the racks. She purposefully moved her arms in a manner that caused the lower half of her top to raise up momentarily, giving Tim a very brief view of her panties.

It had been several weeks since Sadie initially caught Tim peeping on her. She was enjoying the attention. One evening after she had been out at happy hour with a girlfriend and had several drinks, Sadie was feeling particularly frisky. She was in her room at her normal bedtime. She confirmed Tim's room was dark with the faint laptop glow in the corner. Sadie couldn't see Tim, but she knew he was watching.

Sadie undressed in view of the window as she often did. This time, she stripped naked and laid on the bed with her back against the headboard. Sadie proceeded to masturbate as she leaned against the headboard. Tim couldn't believe it. He quickly removed his hard cock from his shorts and started jerking off. He was so turned on he couldn't help himself.

Sadie felt a little naughty knowing Tim was almost certainly watching her. It wasn't long before Tim lost it and came all over his hand. Sadie continued for a while until she arched her back, bit her lip and came. Sadie enjoyed it so much, she made a new habit of masturbating like this a few times a week where Tim could see her.

A few weeks later, Tim was in his room and he noticed Sadie's lights go on. It was a bit earlier than normal so caught him off guard. He stumbled across his room and turned his lights off. Sadie didn't see him, but she did notice his light go out. To Tim's surprise, Sadie wasn't alone. There was another girl with her. She was also attractive and appeared about the same age as Sadie, with a similar height and figure.

The girls sat on the bed for a while and talked. Tim continued watching from the darkness of his room. After a while, Sadie leaned forward and kissed the girl. Tim was shocked and excited. He continued watching intently as they made out. The girls slowly peeled each other's clothes off and were soon down to their bras and panties. Tim pulled his cock from his shorts and started jerking off as he watched.

The girls continued kissing on the bed for a bit. Eventually, Sadie got up and went to the window in her bra and panties and drew the drapes closed. However, the lights staid on for quite a while after the drapes were shut. Sadie did this on purpose to tease Tim and make him wonder.

Tim continued to look out his window. His mind raced imagining what was happening behind the closed drapes. He couldn't believe what he had seen. Tim continued watching, desperately hoping the drapes would be opened. To his disappointment, they never did. Eventually, Sadie's light went out and dashed Tim's hopes of seeing more. Tim eventually fell asleep.

The following weekend on Saturday evening, Tim and Sadie's parents went out to dinner together. Sadie went over to Tim's house and knocked on the door. When Tim opened the door, Sadie asked, "What are you up to?"

Tim replied, "I was just finishing dinner."

Sadie asked, "Can I come in?"

Tim answered, "Sure." Sadie came inside and they went and sat at the kitchen table. Tim asked Sadie if she wanted anything, but she said no. They talked for a bit sitting at the table.

After a while, Sadie said, "Tim, I know your little secret?"

Tim inquired, "Huh? I don't have a secret?"

Sadie continued, "I know you have been a naughty little boy."

Puzzled, Tim asked, "What are you talking about?"

Sadie said, "I know little Timmy has been a naughty peeping Tom. Or should I say peeping Tim? You've been spying on me through my window. I saw you. More than once. I know you've seen me naked."

Tim's face turned red. He fumbled for what to say as he knew he had been caught red handed. He had hoped Sadie hadn't seen him on a couple occasions when he suspected she might have, but now he knew she had caught him. He stuttered, "I... Uh..."

Sadie cut him off and said, "It's ok Tim. I actually don't mind. I'm not ashamed of my body." Sadie raised one leg under the table and put her heel on Tim's chair between his legs. Her bare foot was barely touching the fabric of the crotch of his shorts. Tim was still flustered from being caught and didn't know how to react.

Sadie continued, "Do you think I'm attractive?" Tim hesitated and didn't know how to respond. Sadie asked again, "Do you?" as she pressed her foot into his crotch.

Tim jolted and blurted out, "Yes."

Sadie asked, "Tell me. I want to hear you say it."

Tim remarked, "I think you are gorgeous."

Sadie replied, "Thank you. That makes me feel good. Do you have a crush on me?"

Tim answered, "Yes."

Sadie asked, "How long have you had it?"

Tim responded, "As long as I can remember."

Sadie remarked, "I'll let you in on a little secret Tim. I've always known you had a crush on me. I think its sweet." Sadie paused and then asked, "Have you dated a lot of girls?"

Tim replied, "No, not really."

Sadie asked, "Have you French kissed a girl?"

Tim answered, "Ya, a couple."

Sadie inquired, "How far have you gotten?"

Tim replied, "Mostly just making out and kissing?"

Sadie asked, "Have you gotten to second base?"

Tim said, "I guess that depends on your definition of second base. I've felt up a girl, over her clothes though."

Sadie remarked, "So you are a virgin, then?"

Tim replied, "Yes."

Sadie commented, "Mmm... I really like that. It turns me on a little."

Sadie began moving her bare foot gently back and forth on Tim's crotch, rubbing his cock through his shorts with her toes. Tim was soon rock hard. After a long pause, Sadie continued her inquiry. She said, "I've been wondering if you jerk off when you watch me through my window at night." After a short pause she continued, "It's ok if you do." Tim didn't make any response. Sadie continued, "You've watched me masturbate, haven't you?" Tim didn't answer. Sadie said, "Tim?" as she pressed her foot firmly into his crotch again.

Tim blurted out, "Yes."

Sadie asked, "Tell me what you thought about it."

Tim responded, "It was really hot. I liked it a lot."

Sadie said, "I see." Then she inquired, "Did you watch me with my friend Becky last night?" Tim didn't respond. Sadie said, "Tim?" as she pressed her foot firmly in his crotch again.

Tim replied, "Yes."

Sadie asked, "And what did you think of that?"

Tim commented, "I thought it was incredible. Really hot."

Sadie responded, "I'm glad you liked it."

After a long pause, Tim asked, "So, are you two like a couple?"

Sadie replied, "You are asking am I a lesbian?"

Tim answered, "Ya, I guess."

Sadie said, "No, I'm not a lesbian. I enjoy being with a woman every now and then for fun. It is so different than being with a man. When it happens, it is usually after drinking too much. Becky and I were roommates and sorority sisters in college. We've been close friends ever since. She has a wild side for sure. Much more so than I do. Do you think she is attractive?"

Tim said, "Yes, she was pretty hot too."

Sadie asked, "Hotter than me?"

Tim replied, "No, you are better looking than she is."

Sadie commented, "Good answer. Smart boy. Remember that." Sadie pulled her foot back from Tim's crotch. She stood up from the table and said, "It's getting close to my bedtime. We'll talk later. Sleep well." Sadie walked out of the kitchen and returned home.

Tim went up to his room soon after Sadie left. He was incredibly horny from the conversation and Sadie rubbing his hard cock with her foot. At her normal bedtime, Tim saw Sadie enter her room and turn on the lights. She proceeded to strip naked in her window as if she didn't know Tim was there watching in the dark. Sadie laid on her bed and started masturbating. Tim quickly got out his cock and jerked off while he watched her. He came two minutes later spurting a large cumload all over his hand.

Tim continued watching as Sadie rubbed her pussy. About five minutes later he saw her arch her back and jerk and spasm. After she finished cumming, she drew the drapes shut and turned off the lights.

The next night, Tim tuned in at Sadie's normal bedtime. When he looked, the drapes were drawn closed but the lights in Sadie's room were on. Tim watched hopefully from his dark room. After several minutes, the drapes were drawn open by Becky, followed by her opening the window for fresh air. Tim was ecstatic to see Becky there again. He anxiously awaited what would happen next.

Sadie and Becky sat on the bed talking for about 15 minutes. Then, Sadie leaned in and kissed Becky. They kissed for a few minutes on the bed. Sadie broke the kiss and they both got undressed, stripping completely naked. They kissed some more and eventually got in a 69 position. As they licked each other's pussies, Tim started jerking off.

Tim wasn't sure if Sadie was purposely putting on this show for his benefit. He didn't care. He was so excited he came a few minutes later. He continued watching the girls until they made each other cum. Eventually, Sadie got up and went to the window. She stood naked in the window for a brief pause, shut the window, then drew the drapes shut and turned off the lights.

The following Saturday, Sadie's parents threw a party at their house. Tim's parents were invited, and they drug Tim along with them. There were about 30 people at the party, but all of them were Tim and Sadie's parents' age. There weren't any younger people around other than Sadie and Tim.

Both Tim and Sadie were quite bored. Sadie asked Tim, "You want a beer?"

Tim replied, "Sure."

They walked in the kitchen and Sadie grabbed two beers from the refrigerator. She commented, "Let's go up to my room so your parents don't see. I don't want to get you in trouble." They slipped upstairs and went in Sadie's room. After they entered, Sadie said, "Close the door." Tim closed the door as Sadie handed him a beer. Sadie said, "You don't mind if I get more comfortable, do you?"

Tim answered, "No, go ahead."

Sadie pulled her dress off over her head and tossed it aside. Underneath her dress she had on a pair of small, black satin thong panties and a matching bra. She climbed on the bed and sat leaning against the headboard. She told Tim, "You can sit on the bed if you want." Tim sat down on the corner of the bed and tried his hardest not to stare at Sadie's gorgeous body. They drank their beers and talked for a few minutes.

Then Sadie said to Tim, "Show me your cock?"

Tim was caught off guard and replied, "What?"

Sadie continued, "Come on. You've seen me naked, now it's my turn. Don't be shy. I want to see your cock." Sadie slipped her hands in her panties and started playing with her pussy.

Tim stood up and undid his pants. He pushed them down along with his underwear as his semi-erect cock sprung loose. Sadie commented, "You have a really nice cock." After a pause, Sadie continued, "Show me how you jerked off when you watched me and Becky the other night?"

Tim objected, "I didn't."

Sadie responded, "Don't lie Tim. I know you did. It's ok. Actually, I was hoping you did. Come on. Show me." Sadie continued playing with her pussy with her hand in her panties. Tim hesitated for a second, then proceeded to start jerking off as he stood at the foot of the bed. Tim's cock quickly got hard. Sadie commented, "That's hot. I don't know why, but I really love seeing a guy jerk off." Tim continued stroking his rock hard cock as Sadie played with her pussy.