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Good Times At Cheddar High: Part Two

Richard moves forward toward his first sexual experience
Exploration and Discovery: Richard and Becky take some naughty selfies.

Now that you've read something about Richard's background and earliest encounter with his first girlfriend (and I hope you have had time to read Part One), Richard is now moving forward to new experiences.

By our junior year, most of the guys had seen their girlfriend's tits and maybe felt a little pussy. More stories surfaced at the high school about the guys who were getting laid and the girls that put out. It wasn't until my eighteenth birthday that I felt confident to move to that next level with Becky.

The following Saturday night, again a bowling night for the Johanssons, I readied my plan to fuck Becky. She seemed more willing than ever and I was convinced we were ready for the next step. Anyway, I couldn't leave high school a virgin and bowling season for the Johansson's was ending in June. It was already May and time was getting short.

I pressed ahead with an ingenious plan to get laid. Proposing my idea as soon as we reached her bedroom door I said, "Becky, let's do something different tonight. Let's do some selfies with both of us naked. It'll be something different and fun for a change."

Becky thought otherwise.

I said, "Look, both of your parents grew up in Sweden . The Swedes look at these things differently and I thought you'd have no problem with this."

She turned to me and said without much conviction, "I was born here and it isn't the same as with my folks. "I'm not letting you take my picture naked."

"Well let me show you what I'm getting at here. Turn on your computer and go to that naturist web site I told you about."

She said, "Okay, but nothing will change my mind," as she typed in the web address.

She was really surprised to see totally naked girls and women of all ages walking casually among men and boys. They even had a Junior Miss Pageant like a Miss Nude Sweden contest complete with a bouquet of flowers for the winner.

A girl about Becky's age was the first place winner. The girl's perky breasts were well on their way to womanhood and she had a nice untrimmed pubic mound, but she wasn't as developed as my girlfriend.

Becky replayed the video clip several times before saying, "Hey, I look better than that!"

"Okay," I said, "Let's see."

"You'll laugh."

"I promise. I'd never laugh about something like this."

"Okay, but don't laugh."

"I promise."

She thought for a moment, then said, "You first!"

I didn't argue. When Becky was satisfied that I was totally uncovered, she removed her blouse and bra. There was no surprise as those glorious breasts appeared. Her tits were as magnificent as always. I never could get enough of them.

After taking down her jeans and tossing them on the bed, she said, "Let me put on my robe and then I'll take off my panties."

"Just take 'em off Becky. We don't have all night."

She turned her back to me and slipped her pink lace panties over her knees down to her ankles and then kicked the underwear onto the bed. I was left with a magnificent view of two perfectly round lobes separated with a crack making for a perfect tight ass. Quickly I snapped a few pictures before she could say, "Stop."

"You didn't," she yelped.

"We've just started, so zip your lips," I replied forcefully.

She was shocked because Becky had never heard me be so aggressive before. She didn't say a word as I asked her to slowly turn her body as I snapped more pictures.

The profile view of a female body is something that makes women look so wonderfully erotic. Her breasts fell naturally from her shoulders with those tasty upturned nipples. The anticipation of seeing her pussy was just so powerful my dong stood at immediate attention. She noticed.

"Dick, your thingy is even bigger than last week. What happened? Are you taking Viagra?"

Click ... click ... then I said, "It's not Viagra; it's your sexy body, Becky!"

Blushing, she gave me her sexiest shy smile.

Becky's frontal view gave me my first good look at her pussy. She had it trimmed to fit her bikini but there still was a bush. It was more like what they call a 'landing strip'. I imagined how it would look shaved. She kept turning and I kept clicking.

I think there were about twenty shots before she said, "My turn."

She grabbed the camera and started taking pictures from different angles asking me to move my 'thingy' up or down ...sideways, left and right. Finally it became clear that she was now interested in my balls.

"Hey Becky," I said, "Let's take some of us together."

Biting her lower lip and giving me a pensive look, she said, "Just a couple, okay?"

After a few silly pictures of us making crazy faces, we really got into it with both of us laughing and giggling. Most of it was innocent playful stuff. Each time we tried to do something funnier than the previous picture. Sitting on the edge of the bed let us get more of our bodies in the pictures.

Once Becky sat on my lap as I reached around to grab her tits. She put on her 'naughty naughty' face for the picture. Then she knelt on the bed behind me with my head between her boobs. It made for a very nice family portrait. My favorite was one where she pointed at my cock with a 'WOW' expression.

Anyway, it was fun but it was time for us to get more serious. I put down the camera and quickly climbed on top of her prepared to consummate our friendship only to be greeted by the sound of a car door slamming. Becky's parents were home.

The two of us quickly dressed and agreed never to show any of the photos to friends. As insurance, I insisted that each of us had copies. If one of us let a friend see them, the other would do the same and neither of us wanted that to happen. Becky downloaded the pictures to her computer in a folder called 'Homework'. I went home needing relief. 

I suffered from a severe case of an overactive libido and in dire need of physical therapy. The cure was in my girlfriend's hands but for now, the ball was in my court. I rushed home, closing and locking my bedroom door. I downloaded our 'Homework' folder. Turning on the folder as a slide show, it didn't take more than a few strokes before shooting a load all the way up my chest to my neck just missing my mouth. It was awesome! What a great feeling! Now I wanted to get into Becky's tight little hole more than ever.

Becky's Birthday and the Club: Becky joins a club and Richard buys her a birthday present.

On the way home from school Monday, I asked Becky about us getting together the next Saturday.

"I can't," she said with only a slight hint of disappointment.

"Why?" I asked

"Oh," she was saying, "Sally is givin' me a birthday party. It's to be a toy party with the girls."

"What's a 'toy party'?" I mumbled.

"Well, we check out toys that we'd like to buy."

"What kind of toys?

"Adult toys, silly. Alice has one and she loves it!"

"How'd she get it?" I stuttered.

"Mark bought it for her."

Mark was her new boyfriend. Mark was an arrogant SOB flaunting his movie star looks. Most of the girls thought that he was a hunk! The guys thought he's a major jerk.

I didn't want to pry but had to ask, "You gonna buy one?"

"No," she said, "We just browse the Internet checkin' 'em out. Judy said she might buy one but she was just talkin'. You know Judy, she's always makin' things up."

I got the feeling Becky was dropping a hint. Females have a way of being indirect about their wish list and think guys can read their mind. Anyway, Becky's eighteenth birthday was in twelve days so there was plenty of time for me to explore the possibilities.

Changing the subject I asked, "So what are you gonna do for your birthday, Beck?"

"My folks are giving me a big party on Sunday. It's for the relatives so I can't see you until the Saturday after. But hey Dick, the good news is that my parents are going to their bowling banquet that night and won't be home until after midnight ."

"That's great!" I blurted out.

"Hold on, we're not having sex, if that's what you're thinking."

Women seem to have a crystal ball or some kind of clairvoyance because every time I just thought about stepping out of line, my mom knew what I was thinking! I've stopped counting how many times she said, "Don't even think about it, buddy!"

Becky got into my head the same way. "So why not?" was my pleading response. "If your parents hadn't come home after our selfies, we might have done it last Saturday." Apparently the urgency in my voice had given me away.

"Go ahead and keep dreaming, Dick, because it's not going to happen." Quietly she continued, "Anyway, I've joined the AO Club at church."

"What the hell is an AO Club?" sounding really annoyed. The thing was, I was more than annoyed. I was pissed off.

"AO means 'abstinence only' and we took a purity pledge. A group of us girls got together to make a bond that we all would be virgins until we get married or at least get engaged. We meet once a month to renew our pledge and ask questions. April thought it up and we all thought it was a great idea."

"Like what kind of questions?"

"Some of us wanted to know if it was okay to masturbate. They told us it's a healthy way to avoid intercourse when we can't hold out any longer. The Club thinks it is a good release."

"Have you done it?

"Done what?


"Of course. Haven't you?"

"Yeah, a few times," I lied. Before she could ask me questions about how often I jacked-off or how I do it, I abruptly changed the subject back to her birthday. "What do you want for your birthday, Becky?"

She paused for a few seconds. Showing some apprehension, she was unsure how to answer. Finally she whispered, "I want to see you cum. Would that be okay?"

"Fine with me," I paused and then said, "but it doesn't just happen like going to the bathroom, ya know."

"I know. Maybe I could try fellatio. Some of the girls have tried it with their boyfriends."

Surprised, I replied, "That would work but how about the Club and your bond?"

"It's not exactly the same as having sex."

"Well a blow job is having sex, Becky, and you don't even know how to do it!"

"Yeah, but a blow job is not intercourse and that is what abstinence is all about. The girls pass around copies of Cosmopolitan and we learn a lot from those "Ten Ways to Satisfy Your Man" articles. We watch porn flicks and Sally has a couple for Saturday. It can't be too hard to learn and you can show me how if I don't do it right."

"We'll see," I said enthusiastically but a little bit skeptical.

It's not easy living with the idea of a guaranteed blow job when the event is so far away. Twelve days was an eternity and the days went by at a snail's pace.

The first Saturday came and went uneventfully other than doing some surfing of my own. I did some toy shopping online and found just what I was looking for at the Pleasure Store. I ordered the Doc Johnson realistic "Kong dong." I bought the vibrating model since it was only a few bucks extra. The Kong was chosen because it looked the most like my cock and was almost as long at nine inches. It was to be delivered in a plain brown box including a 'Love Card' in a gift wrapped box inside.

It would be fun to see Becky's reaction. The most difficult thing was keeping my hands off my penis. I wanted to wank my joystick at every thought of Becky going down on me. However, it was important to keep everything in reserve. I wanted her to get a full load and by 'full' I mean a tank full with extra in reserve in case of a replay. The anticipation was killing me and self discipline is highly overrated.

There was one more thing that puzzled me. Several of the girls in that AO Club were definitely not virgins, at least according to some friends of mine that I trusted. I have to remember to ask Becky why they are members.

After the weekend I called her to ask if we were still on for Saturday evening. We were, but there was a slight change in schedule. I couldn't come until eight because the banquet didn't start until later. I asked how Sally's party went.

"It was fun. Everyone told a story and some of the girls gave pointers on how to give a good blow job. The funny thing was that Alice and Sally got into an argument over trying to deep throat their boyfriend. Sally said you need to practice to avoid something called the gag reflex and Alice said you don't have to go that far to make a guy cum.

Most of us wanted to know how to practice so Alice got out a banana, put a condom on it, and smothered it with whipping cream. We tried to deep throat it like we saw on the vids. Then we had a contest to see who could get it down their throat the furthest without gagging. Sally won, of course, but I came in second!"

I had a thousand questions I wanted to ask but then she said, "What did you do this weekend?"

"Oh, I shot some hoops in the back yard and caught the Badger/Illini game on TV. Other than that, I did homework and thought about you. Hey, I gotta go. Catch ya at school. Bye." I didn't tell her everything especially about Beaver Hill.

Saturday finally arrived. Driving to the Johansson's with Becky's birthday present securely hidden in the trunk, I wondered if Becky was serious about watching me cum. I swear my balls had turned blue in anticipation! It was a little early when I rang the doorbell. I waited for Becky to answer the door, standing there with passion in by heart, lust in my brain and desire everywhere else.

The door opened and Becky gave me a tentative hug. She was wearing an over-sized crimson Bucky Beaver sweatshirt over a pair of white short shorts, an unlikely combination of winter and summer apparel. But that's pretty much like the climate in Wisconsin . You just never know about the weather in May.

In the kitchen we could hear her parents having an argument. Mr. Johansson was saying in a thick Swedish accent, "Bridget, stop flirting with Bob. I'm tired of it and you are making a fool of yourself."

Mrs. Johansson sounded upset. She said, "Look, Bob is a good friend. If you don't want to go tonight, don't but I'm going."

Oh no, I thought. This definitely would not be good. It was easy to understand why Mr. Johansson was jealous. His wife, Bridget, was beautiful. For being in her mid-thirties, she was by far the hottest babe in town making it easy to see where Becky got her good looks. Rumor had it that Bridget had been a model and even posed for Playboy but no one had actually seen the pictures.

There I was ready for Becky's promised seduction with my pubes trimmed, balls shaved clean, and an 'appliance' hidden in the car and her parents might not be leaving the house! Becky gave me that "What can I do?" shrug along with a frown. It is hard to know what happened next. There were a few more angry words spoken in Swedish, but a few minutes later the door slammed and they both got into the car. Their Volvo sped away like the get-away car in a bank heist.

Time Out: Dick and a friend try a practical joke on their buddy at Beaver Hill

Let me backup for just a moment to tell about an event that happened the night Becky was at her 'Toy Party' with the girls. That night I was at Josh Fillman's house drinking beer and checking out Facebook, Twitter, and Tumblr hoping for some fun gossip but there was nothing new or exciting. After a few beers, we were bored.

"Hey Josh, where's Bernie tonight? Ya think he's screwing Samantha?"

Josh had just finished his fourth or fifth beer when he nodded and said, "They're probably up on Beaver Hill."

Beaver Hill is where all of us went to make out with our girlfriends. Becky and I had been there a few times, but only if there wasn't something better going on. Neither of us really cared to be seen there on a regular basis. Of course, there were the 'regulars' and it wasn't unusual to see a dozen cars on the Hill.

"Dick, I've got an idea. Let's go up there and scare the shit out of Bernie."

"How do you mean?" I asked.

"Well, I'll wear my brother's hat and we'll sneak up to the car and pretend like cops."

Josh's brother was on the local police force but was somewhere in the Northwoods shacked up with his girlfriend.

"Gee, I don't know. Ya think Bernie will fall for it?"

"Sure. I'm practically my brother's twin so he's sure to think it's my brother."

"Okay, I'm all in but remember, it's your idea and I'm just comin' along for the ride."

"Yeah sure," he said. We're in this together pal," as he went into another room to get his brother's police hat and a flashlight.

Josh parked his car at the foot of the hill and we quietly climbed to the top trying very hard not to laugh. We were beside ourselves with anticipation of our practical joke.

Reaching the top, both of us were surprised to see only one car.

"Dick, is that Bernie's car?" Josh whispered.

"I don't know. I think so. It's kind of dark."

Josh said, "Let's get closer. You hold the flashlight but don't turn it on until I yell. 'Cops'."

"Okay," and we quietly snuck closer to the car.

It was obvious that Bernie was having his way with Samantha from the sounds coming from inside. As we crept closer and nearly close enough to touch the car, the girl yelled, "Harder, fuck me harder!"

All we could hear from him were grunts and the car seemed to be bouncing. Josh and I looked at each other and whispered, "Now."

At the top of his lungs, Josh yelled, "Cops! Get out of the car."

At the same moment I beamed the flashlight through the window flooding the back seat with light. Her legs were spread and almost touching the ceiling while his hips were between her legs with his pants around his knees mooning us with a naked ass. At once the two of them turned to look at us and their eyes glared like deer in headlights.

"Oh my God," Josh and I said simultaneously. It wasn't Bernie and it wasn't Samantha. It was Mr. Klein, the vice principal, who was on top of Alice, the captain of the cheerleader squad. To make this even more ironic was that it was Alice who invented the AO Club scheme that Becky had joined.

The two of us fled down the hill like Olympic sprinters and sped away in the car without looking back.

I was left with a dilemma. Should I tell Becky?

The Promise: Becky tries out her birthday present with Richard's help

So, the Johansson's were off to their bowling banquet and I was ready to capitalize on Becky's promise. Both of us were a little nervous and I was overflowing with sexual desire! In these situations, a little small talk goes a long way.

"How does it feel to be 'legal'?" I asked.

"Great! It's better than seventeen knowing I can go and get a beer with friends without feeling really really guilty."

"Yeah, I know what ya mean. How was Sunday's party?" I continued.

"Oh, okay. Ya know how the relatives get. Uncle Sam drank too much, as usual, and tried to kiss me while Aunt Margaret was all teary saying, "My Rebecca is no longer a baby." Everyone means well but I'm glad it happens only once a year. Let's go upstairs and I'll show you my oil painting."

"I'm more than ready!" I said with enthusiasm, maybe even too enthusiastically .

I followed her up the stairs watching Becky's tight ass sway as she led me to her bedroom. She was wearing short cut off jeans that heightened my desires with every step. Once in her bedroom she dug out a canvas hidden in her closet.

"It's not quite finished," she explained.

It looked quite finished to me but it was not like the David statue. She had painted a marvelous monster cock in cool colors. The gleaming oils made it look three dimensional.

"Wow, it looks great!" I told her and meant it. "What do you have to do to finish it?"

"You'll see!" she said with a wink and a smile.

"Hey, why didn't you do me like that guy David?"

"Well, I thought about it and decided to paint the best part of you."

"I see, sort of. I have something else you can explain. How come Judy and Penelope are in your AO Club? They've been having sex ever since freshman year and not with just one guy."

"Well, I don't know about that," she said rather defensively. "Anyway, 'AO' means 'Abstinence Only' so even if they aren't virgins, they have sworn not to have sex again until they are engaged or married."

"That's walking a fine line, Becky."

"Well, that's the way it is and you can stop asking me about it."

I wondered how to break the ice and get on with the evening's activities. You don't just say, "Pull down my pants and shove this thing in your mouth," although that idea was flooding my brain at the moment.

"Hey," I said, "I've got something down in the car for you. Wait a minute while I go get it."

"What is it?" Becky asked as I ran downstairs.

"A birthday present," I yelled back.

Wrapped in purple and yellow paper with a gold ribbon, I handed Becky a box just a little smaller than a shoe box.

"I can't wait!" she squealed.

"Me too," I said under my breath.

Becky pulled off the ribbon and carefully undid the wrapping. had done a nice job of gift wrapping. Inside was a small card with Becky's name on it. The card read, "With affection ... Love, The Hose."

Peering deeper into the box and unfolding blue tissue paper, she began to see the super sized penis. "Oh my God," she screamed. "I don't know what to say. You shouldn't have," she mocked with a broad smile. Holding it up for me to see, she said, "I think it looks a lot like you."

The Kong came with a small tube of KY jelly. I thought that was a nice touch.

"Glad you like it, Becky. Let's try it out, okay?"

"Maybe, maybe some other time," was her reply. 

She put her arms around my neck and gave me a motherly peck on the cheek as if I was a small boy. It wasn't the erotic kiss that I'd expected. Something snapped inside of me at that point. Without thinking, I took the bottom of her sweatshirt and quickly pulled it over her head. My God, she wasn't wearing a bra!

"What do you think you're doing?" she said angrily.

"We're gonna do what you promised."

"I didn't promise anything. I just said I wanted to see you cum."

"Right and then you said you'd give me a blow job."

"I said I might do that but it wasn't a promise."

She seemed to be walking a fine line again like practicing to be a lawyer. Enough was enough ... I grabbed her arm as she turned to walk away and gave her a big bear hug and kiss saying, "Your perfume is turning me on and you look so sexy. Let's enjoy tonight and make it a special birthday."

"Okay, but don't be so rough."

I started to unbutton my shirt, but as I got to the second button, Becky came up to me with tears in her eyes.

Sobbing she said, "I'm sorry. I wanted tonight to be perfect and it hasn't started out that way. Your birthday present is really nice but my parents have been arguing all week and then tonight they almost didn't go to the banquet. Then you seemed a little weird at the door tonight, like in a trance, so I wasn't sure what you were thinking."

Removing my shirt, I kept telling her, "I understand ... I understand. It's okay." I gave her another hug but not the bear hug this time but a more delicate, romantic encircling of my arms around her naked shoulders. I felt her breasts against my bare chest and my cock came to life.

"Look, I'll take off my pants," I told her. "Then you can do what you want."

I sat nude on her bed while she stood before me with a quizzical undecided look on her face. Finally she decided to follow my lead and began to move her shorts over her knees and down to the floor. Becky was wearing a scarlet thong in the shape of a heart. Wow, she really did want to make tonight perfect.

"Should I take this off?" pointing to the tiny garment hardly covering her pussy.

"Can you turn around first?" I said as more of suggestion than a question. As she turned, that perfect tight ass came into view and a small strip of thong stuck inside her crease. "You're perfect," I said. "Go ahead and take it off."

"Good God!" I stammered as the scarlet garment revealed this girl's succulent honey pot.

"I thought you'd be surprised," she said with a seductive smile.

"What gave you the idea?"

"Oh, I don't know. It just seemed kind of sexy. I was so horny after Sally's party last week I came home and shaved it all off. Maybe I was too impulsive."

"No, it's great, Beck!" She stood before me with an exquisite cleanly shaved pussy. It was as bald as on a new born babe. "Wow," was the last thing I said before taking her in my arms and giving her the deepest French kiss I could manage.

Soon we both were lying on her bed exchanging kisses and touching places that once were called 'inappropriate'. They were now, very appropriate. I was the honey bee ready to suck the nectar. She was the honeycomb waiting for the pollen.

She kept saying, "Kiss me, Dick, kiss me."

I did as I was told.

She must have felt my elongated erection against her smooth belly by now. The warmth of her body and the tingling sensation of her touches only made for a more erotic moment. Her responses told me she felt the same. My kisses turned to her inflamed nipples and she moaned as they were suckled, first the left and then the right, back to the left.

"Kiss me deep," she whined and I did as she asked.

Her lips were moist and her tongue circled mine as they danced the tango.

"Kiss me lower," she pleaded and I returned my attention to her candy tits. Her breaths began to deepen and it was then she took my hand, guiding it down to her sizzling tight little box.

Becky's pussy lips were pouty, like Angelina Jolie's collagen lips, plump and tantalizing, smooth, soft and wet. As my finger began to probe the inner portion of her labia, she brought her ass off the sheets encourage my exploration. All the while Becky was letting out a whimpers of lust. Her juices made for a slippery entry as my finger explored ever deeper.

I was up to the second knuckle when she cried, "Deeper, Dick, deeper."

She was getting a good finger fucking while I added a second and even third finger, thrusting in and out of her dripping cunt. Becky was wild with excitement. I could fuck her properly now and she was not about to object.

Instead, I grabbed big Kong. I smeared it with the sex juices covering my hand and placed it's head near her clit. "Strike while the iron is hot," is the over used cliché but it fit the moment. Something was definitely hot. This was the moment to strike and have Kong buzz Becky's clitoris.

Quickly I dialed the giant dong making it produce a low hum as it began to vibrate. Tenderly and delicately the buzzing Kong made contact with her clit. The stimulation of her love button raised her arousal to another level. At the first touch, Becky put out a shriek of total passion. I was out of my mind with lust and desire. My insides were about to burst.

I needed release soon but kept on pleasuring Becky with her vibrating appliance.

"Finger fuck me. Fuck me hard," she demanded.

While Kong was at work polishing her gemstone, I stuffed a couple of fingers back into Becky's dripping pussy, working them in and out until she was near exhaustion.

As I pulled out, she said in with a rasping voice, "Don't stop, don't stop!" There seemed to be no end to this girl's cravings. 

At her insistence, I took Kong and entered him slowly past her swollen slit. Again she was begging me to push in deeper. Pushing Kong in slightly was just a tease then I put it in half way, out again then further up, out again, and finally, all the way in. All nine inches of Kong were inside my adorable girlfriend.

With each step of the way, she cried out, "More, more!" with an intensity that surprised me. 

"Pump it! Pump me!" she yelled spreading her legs as far apart as possible to accommodate the sensation. Turning up the volume to full vibration, the dong slid effortlessly in and out while I sucked on her little pink pearl.

She panted, then yelled, "I'm cumming ... I'm cumming," in a less than lady like voice while wildly thrashing her hips to meet Kong with each stroke.

And then it was over, just like that. Her orgasm was explosive and she was exhausted. Never could I have imagined Becky to act like such a slut. She was hot. She was horny. She was wonderful.

------- to be continued

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