It had been a long ride from the airport to Gram's house and her grandmother was tired and turned in early. Caitlyn wasn't tired though. She was lying in bed thinking what a train wreck her life had become. A year ago she could not have imagined doing the things she did last year but she had been like the frog in the warm water. The water gradually got warmer over time until it was too hot and she got burned.
I was a senior in high school and then my dad got transferred a job in Los Angeles.
I was apprehensive about moving to a different place but also excited to be moving to LA. I wasn't much of a winter person and the winters got very cold in the Midwest. I was looking forward to the dry sunny weather. The sun always perked me up and my mind was filled with the glamorous stereotypes of California, movie stars, beautiful scenery, the latest fashions and trends.
When we left home it was freezing and the ground was covered in a foot of snow. When I walked off the plane my skin was caressed by a heavenly 70 degree breeze and the bright sun almost overwhelmed my eyes. I couldn't believe it! This was my new winter? On the drive to our new home I saw palm trees. I had never seen a real palm tree before. Incredible! The house styles were so different. Stucco houses with beautiful tile roofs and cactuses in the front yard. People were wearing shorts and t-shirts in December! It was so cool!
My new house was beautiful and I loved the neighborhood and was bursting with excitement as I lay in bed that night. It took quite a while to get to sleep.
Everything was wonderful at first. Caitlyn quickly made friends with the kids in the neighborhood. It didn't hurt that she had a beautiful face and body. She was soon friends with all the 'in' girls and they quickly brought her up to speed. They all went to the same school and she fit in right away.
Some of the things her girlfriends talked about definitely shocked her though. Many had been dating for a long time and had moved way beyond what she had done. A few had even had sex. She didn't want to seem like a fool so she just nodded her head to make it seem like she was cool with everything even though she had barely done anything.
Her best friend Judy, was one of the more experienced girls and quickly guessed Caitlyn's secret. One day they had a heart to heart and Caitlyn admitted her inexperience. Judy was fabulous and agreed to set her up with a guy that she had dated. A week later she had gone out on her first date after a little pre-date pep talk from Judy.
"Now remember Caitlyn, Kevin is a very nice guy but he'll expect a bit more than what you may be used to. He's going to expect kissing and some touching so don't make a big deal when he tries, after all it's nothing."
I had a great time with Kevin. He was friendly and attractive and we were quickly kissing and touching each other. I couldn't believe how good it felt. I could have just kissed him all night long and when he touched my breasts I really got excited. This was definitely something I wanted to do again and soon!
Judy was so helpful. She took me to the local clinic and got me on the pill just to be safe. It didn't take long for Kevin and I to move beyond kissing and touching. We were both masturbating each other in no time and Kevin showed me how to give a good blow job and he definitely knew how to eat pussy. I never felt such pleasure in all my life!
I lost my virginity to Kevin. He was very gentle and after the initial pain it started to feel really good which I heard later was unusual for the first time. After that we had sex ever chance we got and tried everything we could think of. I quickly learned what I liked and didn't like and started to get very good at pleasing Kevin. Eventually I could even deep throat him and discovered all the sensitive spots on his body that really turned him on. In turn, he made me realize I liked to be on top, showed me my G-spot which I wasn't even aware of, and did everything he could to please me.
I'm not sure if Judy had decided that my 'training' with Kevin was finished but at one point she said I was ready to move on. She fed me a constant stream of new guys that she had already sampled and pre-approved and I didn't waste any time. Some of them I didn't like and just went out with once but by then I loved sex and most of her referrals were very pleasing to look at and be with and knew what they were doing. I had a great time.
After a while our high school started to seem like a fish bowl. We had dated most of the senior guys that we wanted to so Judy and I moved on to parties with older guys and guys from other schools. There were always lots of older guys interested in attractive high school girls and there was lots of free booze and pot at these parties which seemed great.
That's when things started to sour with my parents. It was one thing to explain coming home a bit late. Judy and I always had our stories planned so they never suspected anything. It was a bit harder to explain not coming home at all or coming home totally out of it and not remembering at breakfast the next day what lie you told the night before.
Expanding our dating territory also meant that we were frequently in unknown territory. There were many times when we hardly knew any of the guys at a party. Most of the guys were usually nice but sometimes they definitely were not. Some of them had never heard of the expression 'no means no' and some of them liked it rough even if we didn't.
As long as Judy and I were willing to be 'friendly' we could have whatever we wanted but after a while I started to feel uncomfortable. My relationship with my parents was strained. Waking up and not remembering what happened the previous night was an unpleasant feeling. Waking up and remembering what happened the previous night was sometimes even worse.
Here's the thing though, we are all prisoners of habit. Judy and I had done our 'thing' for so long that I could not imagine anything different. We were part of a group that all did the same thing and to me it seemed perfectly normal to be partying and having sex on a regular basis. It was the norm I was used to.
It all came to a head one night when Judy got roughed up fairly bad. I called her parents and called mine and then started to cry and cry and cry. My cool LA lifestyle was not so cool anymore but I knew if I stayed I would be unable to break out of the rut I was in and sooner or later, I might be where Judy was.
Thank God my parents realized the same thing and intervened. One day my Gram showed up and my parents told me I was leaving to live with her for a while. They made me pack and got me on a flight back home before I had a chance to come out of my shell shocked state.
Here I was, lying in bed at Gram's house, back where I was born, thinking about my screwed up life.
A bit about Gram. She was my mom's mom and a very strong willed woman. Apparently, she was a bit of a wild child in the 70's but managed to survive and eventually opened a women's clothing store which thrived over time. I had always had a special relationship with her. She treated me like an adult and it's her I turned to when I had sexual questions. My parents knew I respected her and that she wouldn't take any shit from me.
The next morning Gram was friendly but business like.
"Caitlyn, I don't care what happened in LA and I'm not here to judge you but I also expect you to live by my rules while you're in my house. I run a business and can't be watching you all the time and I expect you to behave while you are here. Are we clear?"
'Yes Gram."
"Consider this your second chance in life. Sometimes people don't get a second chance. Sometimes they just die like your friend almost did. Your parent's already called the local high school and explained the situation. You need to go down tomorrow and get registered so you can finish out your last term of high school. She went to leave and turned around and gave me a big hug. "You can't undo what you did but you can make a new start. Consider this your chance."
For my first day at school I wanted to be invisible. I wasn't ready to talk to anyone. I wasn't ready to make any friends. I wasn't ready to have any guys stare at me. I didn't want to explain to anyone who I was or where I had lived. I put on my baggiest track pants and a huge fleece sweat shirt to hide my body. No make up, no perfume, nothing. I pulled my hair back into a tight ponytail and covered my face in a baseball hat and hoped my plain outfit would keep everyone away.
The nights and weekends were the hardest. School kept me busy and kept my mind distracted but at home I was alone except for Gram and she was frequently at her store or out with friends. My mind kept wandering back to my life back in LA and to all the mistakes I made. My behavior looked incredibly stupid and immature and hurtful from a distance. Gram did her best to comfort me and kept telling me it was going to be okay but it didn't seem like it.
Then I saw him at school. He was way bigger than the little runt I remembered and his face had changed somewhat but I was sure it was him. It was Jared, and all of a sudden a surge of happy sweet innocent memories flooded my mind.
Jared and I were best buds or junior soul mates when I was little. We lived next door and did everything together. Jared's parents were always fighting so Jared would often flee to the quietness of my house and to adults that weren't always screaming at each other. My parents went out of their way to treat him like one of theirs. We were always together, at my house, or playing outside or exploring on our bikes. We talked to each other about anything and everything.
I was excited but too nervous to approach him so I put my head down, turned around and walked away as quickly as possible. All the way home though, my heart was pounding and I couldn't get him out of my head. That night I drifted off with excitement about what the next day would bring.
I woke in the morning feeling wonderful. For the first time in a long time I slept great. For the first time in a long time I wanted to get out of bed. In fact, I almost jumped out of the bed, feeling light as a feather, eager to get going. At breakfast Gram stared at me for a while until she finally said, "You look like the cat that ate the canary. What's up?"
"Gram do you remember Jared?"
"Would that be the Jared that you were joined at the hip with for years and the Jared that you wanted to marry when you were eight?"
Caitlyn blushed at the memory of her marriage proposal.
"Yes Gram, that Jared. Does he still live around here?"
"As far as I know. I think I saw him about a year ago."
"Thanks Gram.'
Caitlyn was so excited. She literally felt like she was going to pop out of her skin! All she could think about was reconnecting with Jared but she wasn't ready yet. She was too nervous. She needed to make sure it was him, so she put on her trusty camouflage outfit of baggy track top and pants, ponytail, no makeup, baseball hat and shades. She didn't realize it but she had a huge grin on her face the entire walk to school.
The school was not that big and there were not that many senior classes so she figured he must be in at least one of her classes. She sat at the back of each class and watched the people come in. It didn't take long. He was in her second class and the teacher asked 'Jared' a question.
It really was him! When class was over she left as quickly as possible, still unable to approach him. Later in the day she saw him walking down the hall straight towards her or at least it seemed like that to her. She turned around against a locker and waited for him to go by. After he passed, she quickly turned around to walk away but ran head on into someone coming the other way. Her books and hat and glasses went flying all over the place and she fell to the floor.
Oh my God, could this be any more embarrassing! She quickly realized she wasn't hurt but there were a few snickers and she realized she had lost her hat and glasses. Someone leaned over and asked if she was okay. She looked up and it was Jared! Without her hat and glasses and with her ponytail, she looked similar to what she was like when Jared would have seen her last.
"Caitlyn?"
"Caitlyn, is that you? It's Jared, don't you remember me!"
The cat was out of the bag. There was no point in pretending anymore.
"Jared, is it really you?"
He pulled her up and gave her a huge hug.
"Oh my God! I can't believe it's you! I didn't think I'd ever see you again!"
Jared's parents had eventually split and he and his mom had moved into a small apartment in a different part of town. Jared ended up going to a different high school. It was heartbreaking for both of them and at first they stayed in touch but over time they gradually drifted apart.
For the next few weeks, Jared walked Caitlyn home from school. Within a very short time it was like they were never apart. They were older but they still had the same connection they had earlier. Their personalities were a perfect match. Caitlyn felt totally comfortable around Jared. She would never have even considered going to school in her baggy sweats with no makeup at her old school but she was so relaxed around Jared that didn't even think about her clothing or putting on makeup.
Not everything was the same though. Caitlyn wasn't a young tomboy anymore and Jared's body had definitely filled out. He was almost six feet tall and had a lean muscled look. He had a cute face and a tight butt. She couldn't stop sneaking peeks at him!
After a few days she reached over and held his hand on the way home and he didn't seem to mind. They had never touched before and it felt good. Their whole relationship became more physical. Everyday conversations were now filled with gentle pats and touches and squeezes and they always greeted and left each other with hugs. They couldn't keep their hands off each other. It didn't take long for them to start making out at her Grams house. They would sit on the couch and kiss and run their hands all over each other.
One day Caitlyn decided it was time. She couldn't be in love with anyone more than she was with Jared and she knew he felt the same way about her. They made out passionately on the couch for a bit and then Caitlyn lifted up and pulled her shorts off and started to unzip Jared's pants.
"What are you doing?"
"I'm taking your pants off so I can get at you! You don't mind do you?"
For Caitlyn it was a rhetorical question but Jared wasn't answering and he wasn't taking his pants off.
She moaned softly in his ear, "Come on Jared, I want you, I'm ready. Take your pants off."
Jared still wasn't moving and Caitlyn finally realized that something was wrong.
"What's wrong?"
After a bit, Jared softly said, "I've never been with anyone."
"Ya, right!"
Jared wasn't kidding though.
"Oh Jared, I didn't know."
She could believe someone as nice and attractive as Jared, had never been with anyone. How could that be? With her background she just assumed he had been with other people like she had.
She tried to be reassure him. "It okay, I have. I can show you."
"Really, you've slept with other guys?"
A loud alarm bell went off in Caitlyn's mind. In a matter of seconds her dream off finally being with Jared seemed to be going up in smoke. She was so surprised by the sudden turn off events that she wasn't sure what to say. Jared didn't give her a chance.
"How many guys have you slept with?"
Caitlyn was stunned and just stared at Jared. She knew the truth was not going to go over well but she couldn't lie to him.
"I don't know the exact number but a few."
"How could you not know how many? How many is a few, four, five, six?"
"Higher."
The silence from Jared was deafening and after a minute he got up and said, "I need to go okay. I'll talk to you later."
Caitlyn waited for Jared to call but days went by and he never did and he avoided her at school. Finally she couldn't take it any longer and called him.
"Jared, can we please meet? I know you're upset but we really need to talk. I need to talk to you, to explain."
That night Jared came to her place and Caitlyn explained how she went from shy girl to party girl. She explained how exciting it had been at first and how she got in with the cool girls and how they gradually introduced her into their lifestyle. How all of it happened slowly and seemed normal. It was fun and exciting and everyone around her was doing the same thing. Then she told him about how things started to go down hill with the booze and dope, waking up not knowing what had happened, the occasional violent dates and the terrible arguments with her parents and the final night in the hospital with her badly beaten up friend.
"I was really depressed when I got to Grams, thinking of the train wreck my life had become and how badly I treated my parents. I couldn't sleep, I didn't want to go out. I hid at school under baggy cloths. I had no appetite, no energy, I just wanted to stay in bed all day.
Then I saw you at school and had a wonderful flashback to when we used to be together and how much fun we had. It made me remember what I used to be like and for once I went to sleep happy and woke up looking forward to the next day. I've never been so happy since we've been together again and I can't stand the thought of loosing you but I won't lie to you and I can't undo the past."
Caitlyn started to tear up.
Jared instinctively hugged her because he loved her but everything was not okay. In a purely intellectual sense hearing her explanation helped. Everyone made mistakes and it was easy to get in with the wrong crowd. Knowing what happened helped blunt the lump he'd had in the pit of his stomach over Caitlyn's lovers but the feeling was still there. It was one thing to understand the why but it was another to accept the what. She had been with him almost the whole time she was back and she was the same beautiful person that he loved before but how could he get over what he knew?
"Caitlyn, I appreciate you explaining everything but I'm still having a hard time. I just need more time, okay? I just need to be alone for a bit. I promise I'll call you."
Days went buy but he didn't call. Caitlyn knew she somehow needed to reach him or things might be over but how? Then she had an idea. It might blow up in her face but she had a plan and got Jared to come over again.
She didn't waste any time. She knew what the problem was and needed to get the truth out on the table.
"Jared, I know your upset with the number of guys that I slept with. You think I'll be comparing you to them and not be satisfied"
All along he felt terrible about knowing Caitlyn had slept with so many guys but his ego would not let him articulate it. Now she had said it. He felt sexually inadequate and insecure. He had never slept with anyone. How could he ever please Caitlyn with what she had experienced.
"Yes."
"What if I told you that I've already made the comparison and am 100% confident that you'll be a better lover to me than any of the others?
"What do you mean? How could you know? We haven't done anything sexual."
Caitlyn was nervous. She knew she it was crucial what she said next.
"I know, because making love is always better than just having sex. Sexual satisfaction is mostly a state of mind and I've never been in a better state of mind then when I'm with you. I'm attracted to you physically and I love being with you and I know you love being with me and would do anything to make me happy. I never worry about you hitting me. I never worry about you talking about me to others. I never worry about you using me then walking away. I know you'll never ever hurt me in any way."
"Not one of my past boyfriends, not a single one of my so called lovers ever felt that way about me and I never felt that way about them! They had sexual experience but there was no love. I may have had sex with others but I've never made love with anyone. That's why I'm 100% confident that you will be a better lover to me than any of the others. I know that whatever sexual experience you lack you will easily learn.
"But what if I can't learn?"
"Jared, I know you can because you love me and will try. As long as you try, it will happen. We are not talking about brain surgery here, it's 90% effort and 10% technique. From your perspective, you're only at 10% because you lack experience but from my perspective your already at 90% because you love me and want to please me. I can show you the 10%. I can show you what I like."
"Let me show you. I have a plan. I propose that we get together and practice, and I guarantee you that in a very short time you will be satisfying me better than anyone ever did."
Caitlyn had been watching Jared's face throughout her speech and it seemed like he was accepting her message but she needed to do one more thing to convince him before she let him go. It was vital that he start to feel confident about himself so she reached over and gave him a deep hug and started to kiss him softly. When he started to kiss her back she gradually increased the pressure and then slipped her tongue into his mouth and in no time their tongues were eagerly caressing and exploring each other.
"Jared that felt wonderful! You are wonderful! Can we continue on tomorrow?" Caitlyn was relieved when Jared, with a clearly pleased look agreed. The first night of her plan had been a success!
The next day was vital. She had absolute confidence that Jared would be a wonderful lover but she had to keep his mind off her past and boost his sexual confidence until he felt secure about himself. She knew that if that they could continue their 'practice' that he would quickly loose his sexual insecurities.
Ever since Caitlyn had been home she had been wearing the baggiest cloths possible to avoid attention but the next step in her plan required a change. She put on one of her tightest pairs of pants and tops. Every curve of her body was on maximum display. She left her hair in a ponytail but did up her face. She looked hot.
Her Gram immediately gave her the arched eyebrow when she came down for breakfast. The arched eyebrow was an evil trick that her Gram learned during the 70's that compelled Caitlyn to immediately reveal any secrets she may be keeping. Caitlyn had frequently confessed way more than required when she was younger based on the power of Grams look, but today she had nothing to hide.
"It's not what you think Gram. I'm not reverting to my old ways. Jared needs a boost to his sexual confidence and I plan on giving him a big one today."
She giggled and twirled around, "Do you think my outfit will help? Also, is it okay if Jared comes over after school the next few weeks for some 'study'?"
"If that outfit doesn't boost his confidence then nothing will but make sure you don't scare the boy and don't be doing anything on my bed!"
Caitlyn left early that day for school. She wanted to make sure she was there before Jared. As the other kids started to arrive Caitlyn noticed the guys gawking at her and the girls checking her out which was the effect she was hoping for.
When Jared arrived she greeted him with a kiss and a big hug that she prolonged for maximum public exposure. Jared's eyes almost popped out of his head. He had never seen Caitlyn done up in such sexual splendor.
"Oh my God Caitlyn, you look gorgeous!"
That was what she loved about Jared, he just blurted out the truth and never played games and she was thrilled with his response. She grabbed his hand and they walked to class together. Caitlyn never missed an opportunity to touch and hug and kiss Jared throughout the day and by the end of the day everyone had noticed Jared and his 'hot' looking girlfriend. As innocent as he was, Jared definitely noticed the looks of envy he was getting and it felt really good! Caitlyn's plan was working perfectly.
"So Jared, see you after school for our next session?"
With a huge grin on his face he said, "Don't worry, I'll be there!"
When she got home she quickly stripped off her cloths including her underwear and put on the loosest, thinnest t-shirt that she could find. The goal was to give Jared maximum access to her body. She could tell he appreciated the view by the way he stared at her when she came out.
"Jared, the first thing to remember is foreplay. You have to start slow and build up the passion. I love soft kissing and being gently touched all over."
Jared leaned over and started kissing Caitlyn softly like she requested. His hands were moving up and down all over her smooth body caressing her gently. It wasn't long before their wet tongues were slowly experimenting with each other.
When Jared started to kiss and touch her she felt like ripping off his cloths and impaling herself on his cock but she knew she had to pace herself and not scare him off. It was really hard though!
"Jared, if a woman is excited you can tell by her nipples being hard and her pussy being wet.'
She grabbed Jared's hands and placed them on her nipples.
"Feel how hard you made them Jared. You did that."
Jared couldn't believe how hard they were. They were sticking out really far and were as hard as bullets. He couldn't resist rubbing and squeezing them which made Caitlyn groan.
Caitlyn then moved his one hand against her pussy.
"Feel how wet you made me."
She moved his hand up and down against her pussy. Then she took his hand and put his now gooey fingers in his mouth.
"Taste me Jared."
Jared eagerly savored the smell of Caitlyn's sex on his fingers and then licked his fingers clean.
"Now lick and suck my nipples!"
Jared started to lick and then suck her nipples softly.
"Harder!"
Caitlyn moved his hand back between her legs and started to drag his fingers up and down her wet pussy.
"Oh Jared, that feels so good. Bite my nipples!"
She pressed Jared's fingers harder and harder against her engorged clit.
"Harder Jared, bite them harder!"
Jared squeezed her nipples harder and harder between his teeth and continued to rub her pussy and in no time he noticed Caitlyn's body start to tense up. All of a sudden she squeezed her legs tight against his fingers and started to shake. Jared realized he had given a women an orgasm for the first time, and it was Caitlyn!"
Jared quickly mastered everything that Caitlyn showed him. It was just like Caitlyn said, 90% effort and 10% technique. Caitlyn showed him what she liked and then he practiced, always watching her to see how she responded. If hard nipples and a wet pussy were indicators of female excitement then Caitlyn seemed to be permanently excited. After their session on oral sex Jared was easily able to bring Caitlyn to multiple orgasms every time. Jared was in Heaven. He was with his sweetheart and doing things he couldn't have imagined a few weeks ago.
Caitlyn couldn't believe how well her plan had turned out. Jared was like a kid in a candy store and her body was the candy. He quickly mastered everything she showed him and was consistently giving her wonderful orgasms with his mouth and hands and fingers. Hell, he could almost make her cum just kissing her!
It was a novel experience being with someone that put her needs first. He wouldn't even let her touch his penis until he had made her cum. He seemed content just to explore and touch her body forever. At the beginning she was frustrated because she was so horny but didn't want to push him but she was definitely going to sleep satisfied the last few nights. It was time for the last lesson.
"Jared, I have a complaint. I've been 'putting out' for weeks and you haven't even asked me out for dinner once! What kind of a boyfriend are you?"
She could barely keep a straight face. Jared's face was all red and he didn't seem to know what to say. After a minute she started to laugh. "I'm just kidding Jared, but I think we're ready for the final lesson and I want it to be special. I want it to be something I'll remember later so it's time for you to wine and dine me. Call me after you've decided where you're going to take me and it better be somewhere requiring a suit!"
She was just kidding, but Jared actually did wear a suit. She didn't even know he owned a suit but he certainly looked good in it. He took her to a fancy restaurant and opened the car door for her and seated her at the restaurant. She felt like a Princess.
Even though it was Caitlyn's suggestion, Jared was thrilled to be taking her out on a formal date. They had slipped back into their old friendship almost immediately after they met at school, which was great, but this time there was something more. A sexual undercurrent quickly developed between them. They didn't talk about it and might not have even thought about it explicitly but it was there. Unfortunately, it all came crashing down the day Caitlyn's sexual history came up. To Jared, Caitlyn was still the old Caitlyn. He had never been with anyone and he just assumed she hadn't either. The discrepancy between his outdated mental image of her and reality was just too much to handle and he fled. Thank God, Caitlyn has persisted in seeing him and thank God she was able to get through to him that he had nothing to worry about and only wanted him. He had to give her credit, her speech on making love versus having sex calmed his insecurities long enough for their practice sessions to boost his confidence.
Now he wanted to return the favor. He wanted to show her how special she was to him, how he now thought of her as his girlfriend and not just a friend, how he now thought of her as a beautiful woman and not just a tomboy girl.
She looked beautiful when he picked her up. It was obvious that she had spent a lot of effort to look good for him and he told her she looked fantastic! He in turn, had dusted off the one suit that he owned and took care to open the car door for her and hold her hand and seat her in the restaurant. Jared noticed the stares that Caitlyn received from the males in the restaurant and felt proud to be with her. She could have any guy she wanted with her looks but she was here with him!
Caitlyn had told Gram this was the big day and asked if it was okay if Jared stayed over. Her Gram really liked Jared and told Caitlyn it was fine. Caitlyn didn't know it but her Gram had been watching their relationship develop and was thrilled at the turn around in Caitlyn's life. She was really worried about Caitlyn when she first arrived but reconnecting with Jared had made a huge difference.
It didn't take long for Caitlyn and Jared to start kissing when they got home and they quickly moved to her bedroom. This time Jared offered no resistance when Caitlyn went to unzip his pants. In no time at all they both were naked and caressing each others bodies with their hands and lips.
Caitlyn was normally an aggressive lover but she let Jared lead the way. It was his night! He knew all her hot spots by now and didn't spare any effort in tending to each one. She was very wet by the time he got between her legs and in no time his magic tongue gave her an enormous orgasm. She was clenching and shaking Jared's head so tight that he was afraid his neck was going to snap!
After her orgasm subsided she pulled him up and grabbed his rock hard cock and gently rubbed it up and down her drenched pussy. Jared thought she looked beautiful lying below him with her long hair spread underneath her.
"I'm ready."
It was actually happening! He couldn't believe it. Jared lined his penis up against her and gently pushed until the head popped in, then slowly moved in and out pushing a bit deeper each time until he bottomed out in her. My God, it felt good! Her vagina was so silky smooth and warm and wet.
She wrapped her legs tightly around his back and held him still for a minute, savoring the feeling. She always loved the feeling of being physically joined, of having someone deep inside her and tonight it felt better than ever due to her intimate feelings for Jared.
After a minute, she told Jared she was ready for more and he started to tenderly move in and out. He never done this before and didn't want to hurt her.
Caitlyn's body was still highly aroused and wet from her previous orgasm and she was ready now.
"Harder Jared! Faster and harder! You won't hurt me."
Jared hesitantly picked up the pace and she seemed okay so in no time he was slamming into her. Her face was flushed and tensed up and her eyes were closed. Her whole body jiggled with the force of each downward thrust and Jared had to pin her shoulders with his elbows to prevent her from sliding into the headboard. Her legs tightly gripped his back pulling him in as deep as she could and her nails were raking him.
Caitlyn's already high level of arousal quickly escalated. His cock felt really good in her. It wasn't huge but the head was quite large and felt wonderful as it pulled and stretched her insides every time he moved. In no time she squeezed her arms and legs around him as tight as possible and started to convulse with another huge orgasm. Eventually the tremors subsided and her arms and legs flopped down on the bed. That's when she realized that Jared was still hard.
"Jared, you're still hard, didn't you cum?"
"Not yet."
She couldn't believe it. She thought for sure he wouldn't last long given it was his first time. He had found though that if he shifted his mental focus from the sensation in his penis to concentrating on her that he could avoid losing control.
He asked her "Are you up for another one?"
"Really?"
Jared took that as a yes and pulled her close and quickly flipped them over so that she was now on top.
'I want you to be on top. I want to watch!"
Caitlyn was definitely ready and loved to be on top. She loved the control it gave her. She could vary the angle of her body to maximize her pleasure.
She sat up perfectly straight, pushing his penis as deep in her as it would go and savored the feeling of fullness in her.
Jared loved the view and the position. They were joined at the groin and he had a beautiful viewpoint looking up at her breasts and face, At first they held hands and intertwined their fingers and she moved up and down on him. Then she started to vary the angle, leaning back or forwards. After a while she picked up the pace and would almost rise completely off him and then slam down hard. A thin sheen of sweat covered her body. Jared loved the slippery feel of her sweaty skin.
She leaned forward and began to grind her sweaty breasts against Jared's chest. Her nipples were rock hard. Jared pulled her ass cheeks against him tightly and then she bent her face down forcing her mouth against Jared's until it opened and their tongues intertwined.
"Fuck me Jared! Fuck me hard!"
Up until now Caitlyn had been doing all the work but Jared quickly wrapped his arms around her back pulling her down tight and started matching her every thrust.
"I'm getting close Jared, cum with me!"
Jared was ready and immediately shifted his focus to the exquisite pleasure of Caitlyn's pussy. The pleasure in his cock quickly reached a crescendo. His balls tightened up and then he erupted with a huge orgasm.
The flood of hot sperm deep inside her triggered Caitlyn's third major orgasm and she collapsed, exhausted, on Jared's chest. Their sweaty bodies were stuck to each other, hearts pulsing against each other.
"That was incredible Jared! That was the best I've ever had. My Jared, the stud!"
She meant every word of it. She had never been so satisfied. Who knew Jared had such control! Her body was tired but her mind was already fantasizing at the thought of Jared pumping her for as long as she wanted!
She rolled over on her side and Jared snuggled up against her closely, draping his arm over her stomach, intertwining his legs with hers and pushing his groin against her behind.
He drifted off thinking, "Caitlyn's stud, I like the sound of that!"
"But what if I can't learn?"
"Jared, I know you can because you love me and will try. As long as you try, it will happen. We are not talking about brain surgery here, it's 90% effort and 10% technique. From your perspective, you're only at 10% because you lack experience but from my perspective your already at 90% because you love me and want to please me. I can show you the 10%. I can show you what I like."
"Let me show you. I have a plan. I propose that we get together and practice, and I guarantee you that in a very short time you will be satisfying me better than anyone ever did."
Caitlyn had been watching Jared's face throughout her speech and it seemed like he was accepting her message but she needed to do one more thing to convince him before she let him go. It was vital that he start to feel confident about himself so she reached over and gave him a deep hug and started to kiss him softly. When he started to kiss her back she gradually increased the pressure and then slipped her tongue into his mouth and in no time their tongues were eagerly caressing and exploring each other.
"Jared that felt wonderful! You are wonderful! Can we continue on tomorrow?" Caitlyn was relieved when Jared, with a clearly pleased look agreed. The first night of her plan had been a success!
The next day was vital. She had absolute confidence that Jared would be a wonderful lover but she had to keep his mind off her past and boost his sexual confidence until he felt secure about himself. She knew that if that they could continue their 'practice' that he would quickly loose his sexual insecurities.
Ever since Caitlyn had been home she had been wearing the baggiest cloths possible to avoid attention but the next step in her plan required a change. She put on one of her tightest pairs of pants and tops. Every curve of her body was on maximum display. She left her hair in a ponytail but did up her face. She looked hot.
Her Gram immediately gave her the arched eyebrow when she came down for breakfast. The arched eyebrow was an evil trick that her Gram learned during the 70's that compelled Caitlyn to immediately reveal any secrets she may be keeping. Caitlyn had frequently confessed way more than required when she was younger based on the power of Grams look, but today she had nothing to hide.
"It's not what you think Gram. I'm not reverting to my old ways. Jared needs a boost to his sexual confidence and I plan on giving him a big one today."
She giggled and twirled around, "Do you think my outfit will help? Also, is it okay if Jared comes over after school the next few weeks for some 'study'?"
"If that outfit doesn't boost his confidence then nothing will but make sure you don't scare the boy and don't be doing anything on my bed!"
Caitlyn left early that day for school. She wanted to make sure she was there before Jared. As the other kids started to arrive Caitlyn noticed the guys gawking at her and the girls checking her out which was the effect she was hoping for.
When Jared arrived she greeted him with a kiss and a big hug that she prolonged for maximum public exposure. Jared's eyes almost popped out of his head. He had never seen Caitlyn done up in such sexual splendor.
"Oh my God Caitlyn, you look gorgeous!"
That was what she loved about Jared, he just blurted out the truth and never played games and she was thrilled with his response. She grabbed his hand and they walked to class together. Caitlyn never missed an opportunity to touch and hug and kiss Jared throughout the day and by the end of the day everyone had noticed Jared and his 'hot' looking girlfriend. As innocent as he was, Jared definitely noticed the looks of envy he was getting and it felt really good! Caitlyn's plan was working perfectly.
"So Jared, see you after school for our next session?"
With a huge grin on his face he said, "Don't worry, I'll be there!"
When she got home she quickly stripped off her cloths including her underwear and put on the loosest, thinnest t-shirt that she could find. The goal was to give Jared maximum access to her body. She could tell he appreciated the view by the way he stared at her when she came out.
"Jared, the first thing to remember is foreplay. You have to start slow and build up the passion. I love soft kissing and being gently touched all over."
Jared leaned over and started kissing Caitlyn softly like she requested. His hands were moving up and down all over her smooth body caressing her gently. It wasn't long before their wet tongues were slowly experimenting with each other.
When Jared started to kiss and touch her she felt like ripping off his cloths and impaling herself on his cock but she knew she had to pace herself and not scare him off. It was really hard though!
"Jared, if a woman is excited you can tell by her nipples being hard and her pussy being wet.'
She grabbed Jared's hands and placed them on her nipples.
"Feel how hard you made them Jared. You did that."
Jared couldn't believe how hard they were. They were sticking out really far and were as hard as bullets. He couldn't resist rubbing and squeezing them which made Caitlyn groan.
Caitlyn then moved his one hand against her pussy.
"Feel how wet you made me."
She moved his hand up and down against her pussy. Then she took his hand and put his now gooey fingers in his mouth.
"Taste me Jared."
Jared eagerly savored the smell of Caitlyn's sex on his fingers and then licked his fingers clean.
"Now lick and suck my nipples!"
Jared started to lick and then suck her nipples softly.
"Harder!"
Caitlyn moved his hand back between her legs and started to drag his fingers up and down her wet pussy.
"Oh Jared, that feels so good. Bite my nipples!"
She pressed Jared's fingers harder and harder against her engorged clit.
"Harder Jared, bite them harder!"
Jared squeezed her nipples harder and harder between his teeth and continued to rub her pussy and in no time he noticed Caitlyn's body start to tense up. All of a sudden she squeezed her legs tight against his fingers and started to shake. Jared realized he had given a women an orgasm for the first time, and it was Caitlyn!"
Jared quickly mastered everything that Caitlyn showed him. It was just like Caitlyn said, 90% effort and 10% technique. Caitlyn showed him what she liked and then he practiced, always watching her to see how she responded. If hard nipples and a wet pussy were indicators of female excitement then Caitlyn seemed to be permanently excited. After their session on oral sex Jared was easily able to bring Caitlyn to multiple orgasms every time. Jared was in Heaven. He was with his sweetheart and doing things he couldn't have imagined a few weeks ago.
Caitlyn couldn't believe how well her plan had turned out. Jared was like a kid in a candy store and her body was the candy. He quickly mastered everything she showed him and was consistently giving her wonderful orgasms with his mouth and hands and fingers. Hell, he could almost make her cum just kissing her!
It was a novel experience being with someone that put her needs first. He wouldn't even let her touch his penis until he had made her cum. He seemed content just to explore and touch her body forever. At the beginning she was frustrated because she was so horny but didn't want to push him but she was definitely going to sleep satisfied the last few nights. It was time for the last lesson.
"Jared, I have a complaint. I've been 'putting out' for weeks and you haven't even asked me out for dinner once! What kind of a boyfriend are you?"
She could barely keep a straight face. Jared's face was all red and he didn't seem to know what to say. After a minute she started to laugh. "I'm just kidding Jared, but I think we're ready for the final lesson and I want it to be special. I want it to be something I'll remember later so it's time for you to wine and dine me. Call me after you've decided where you're going to take me and it better be somewhere requiring a suit!"
She was just kidding, but Jared actually did wear a suit. She didn't even know he owned a suit but he certainly looked good in it. He took her to a fancy restaurant and opened the car door for her and seated her at the restaurant. She felt like a Princess.
Even though it was Caitlyn's suggestion, Jared was thrilled to be taking her out on a formal date. They had slipped back into their old friendship almost immediately after they met at school, which was great, but this time there was something more. A sexual undercurrent quickly developed between them. They didn't talk about it and might not have even thought about it explicitly but it was there. Unfortunately, it all came crashing down the day Caitlyn's sexual history came up. To Jared, Caitlyn was still the old Caitlyn. He had never been with anyone and he just assumed she hadn't either. The discrepancy between his outdated mental image of her and reality was just too much to handle and he fled. Thank God, Caitlyn has persisted in seeing him and thank God she was able to get through to him that he had nothing to worry about and only wanted him. He had to give her credit, her speech on making love versus having sex calmed his insecurities long enough for their practice sessions to boost his confidence.
Now he wanted to return the favor. He wanted to show her how special she was to him, how he now thought of her as his girlfriend and not just a friend, how he now thought of her as a beautiful woman and not just a tomboy girl.
She looked beautiful when he picked her up. It was obvious that she had spent a lot of effort to look good for him and he told her she looked fantastic! He in turn, had dusted off the one suit that he owned and took care to open the car door for her and hold her hand and seat her in the restaurant. Jared noticed the stares that Caitlyn received from the males in the restaurant and felt proud to be with her. She could have any guy she wanted with her looks but she was here with him!
Caitlyn had told Gram this was the big day and asked if it was okay if Jared stayed over. Her Gram really liked Jared and told Caitlyn it was fine. Caitlyn didn't know it but her Gram had been watching their relationship develop and was thrilled at the turn around in Caitlyn's life. She was really worried about Caitlyn when she first arrived but reconnecting with Jared had made a huge difference.
It didn't take long for Caitlyn and Jared to start kissing when they got home and they quickly moved to her bedroom. This time Jared offered no resistance when Caitlyn went to unzip his pants. In no time at all they both were naked and caressing each others bodies with their hands and lips.
Caitlyn was normally an aggressive lover but she let Jared lead the way. It was his night! He knew all her hot spots by now and didn't spare any effort in tending to each one. She was very wet by the time he got between her legs and in no time his magic tongue gave her an enormous orgasm. She was clenching and shaking Jared's head so tight that he was afraid his neck was going to snap!
After her orgasm subsided she pulled him up and grabbed his rock hard cock and gently rubbed it up and down her drenched pussy. Jared thought she looked beautiful lying below him with her long hair spread underneath her.
"I'm ready."
It was actually happening! He couldn't believe it. Jared lined his penis up against her and gently pushed until the head popped in, then slowly moved in and out pushing a bit deeper each time until he bottomed out in her. My God, it felt good! Her vagina was so silky smooth and warm and wet.
She wrapped her legs tightly around his back and held him still for a minute, savoring the feeling. She always loved the feeling of being physically joined, of having someone deep inside her and tonight it felt better than ever due to her intimate feelings for Jared.
After a minute, she told Jared she was ready for more and he started to tenderly move in and out. He never done this before and didn't want to hurt her.
Caitlyn's body was still highly aroused and wet from her previous orgasm and she was ready now.
"Harder Jared! Faster and harder! You won't hurt me."
Jared hesitantly picked up the pace and she seemed okay so in no time he was slamming into her. Her face was flushed and tensed up and her eyes were closed. Her whole body jiggled with the force of each downward thrust and Jared had to pin her shoulders with his elbows to prevent her from sliding into the headboard. Her legs tightly gripped his back pulling him in as deep as she could and her nails were raking him.
Caitlyn's already high level of arousal quickly escalated. His cock felt really good in her. It wasn't huge but the head was quite large and felt wonderful as it pulled and stretched her insides every time he moved. In no time she squeezed her arms and legs around him as tight as possible and started to convulse with another huge orgasm. Eventually the tremors subsided and her arms and legs flopped down on the bed. That's when she realized that Jared was still hard.
"Jared, you're still hard, didn't you cum?"
"Not yet."
She couldn't believe it. She thought for sure he wouldn't last long given it was his first time. He had found though that if he shifted his mental focus from the sensation in his penis to concentrating on her that he could avoid losing control.
He asked her "Are you up for another one?"
"Really?"
Jared took that as a yes and pulled her close and quickly flipped them over so that she was now on top.
'I want you to be on top. I want to watch!"
Caitlyn was definitely ready and loved to be on top. She loved the control it gave her. She could vary the angle of her body to maximize her pleasure.
She sat up perfectly straight, pushing his penis as deep in her as it would go and savored the feeling of fullness in her.
Jared loved the view and the position. They were joined at the groin and he had a beautiful viewpoint looking up at her breasts and face, At first they held hands and intertwined their fingers and she moved up and down on him. Then she started to vary the angle, leaning back or forwards. After a while she picked up the pace and would almost rise completely off him and then slam down hard. A thin sheen of sweat covered her body. Jared loved the slippery feel of her sweaty skin.
She leaned forward and began to grind her sweaty breasts against Jared's chest. Her nipples were rock hard. Jared pulled her ass cheeks against him tightly and then she bent her face down forcing her mouth against Jared's until it opened and their tongues intertwined.
"Fuck me Jared! Fuck me hard!"
Up until now Caitlyn had been doing all the work but Jared quickly wrapped his arms around her back pulling her down tight and started matching her every thrust.
"I'm getting close Jared, cum with me!"
Jared was ready and immediately shifted his focus to the exquisite pleasure of Caitlyn's pussy. The pleasure in his cock quickly reached a crescendo. His balls tightened up and then he erupted with a huge orgasm.
The flood of hot sperm deep inside her triggered Caitlyn's third major orgasm and she collapsed, exhausted, on Jared's chest. Their sweaty bodies were stuck to each other, hearts pulsing against each other.
"That was incredible Jared! That was the best I've ever had. My Jared, the stud!"
She meant every word of it. She had never been so satisfied. Who knew Jared had such control! Her body was tired but her mind was already fantasizing at the thought of Jared pumping her for as long as she wanted!
She rolled over on her side and Jared snuggled up against her closely, draping his arm over her stomach, intertwining his legs with hers and pushing his groin against her behind.
He drifted off thinking, "Caitlyn's stud, I like the sound of that!"
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