Diary of a Teenage Boy

Story Info
A busy couple of weeks during 1966.
3.7k words
3.92
4.8k
2
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Saturday

Today was my nineteenth-and-a-half birthday. Thanks mom and dad, but I think that it's time to stop celebrating half birthdays.

Tonight I went to the movies with Susie. As usual, after the movie, we parked on the roadway at the end of the long drive to her house, and we started making out.

Usually, I go straight for her pussy, but I was feeling a bit guilty about this, so I had decided that tonight I would be a good boy and just make out with her. But Susie had other ideas. She became impatient as we kissed. So she grabbed my hand, pulled up her dress, spread her legs, and put my hand in between her legs right next to her pussy, as a clear sign that she wanted me to finger fuck her. It was the hottest thing ever! I guess that she really liked my fingers in her hot little box. So I took care of her, and she had a massive cum.

Sunday

I went to church with Susie and her family as usual. Totally boring of course, but you gotta do what you gotta do. Anyway, there was a new family there this morning - a mom, dad and daughter, who looked to be about eighteen. The daughter wasn't exactly beautiful, but she was h-h-hot!! Her eyes were full of promise, and her mouth just looked like it was made for sucking cock.

Susie's parents decided to go and welcome them. So Susie and I were introduced to the new family. Then Susie asked the girl to come and have a chat with us. Her name was Angela, and she had turned eighteen a few weeks ago, just after Susie did. I noticed a definite spark in her eyes when she looked at me - luckily, Susie didn't notice it. Susie invited Angela to come out with us sometime, and they exchanged numbers.

Monday

Just another workday - how I hate Mondays!

Tuesday

As usual on Tuesdays, I went to Susie's house this evening to watch TV with her family. The shows that they watched were totally boring, of course, but eventually the best part of the evening arrived - the time to say goodnight.

Susie always walked outside with me for a goodnight kiss, or so her parents thought. But as soon as we were outside, I backed her up against the wall and grouped her pussy. She was wearing a little playsuit, and my fingers had no trouble slipping into the legs and finding her pussy. Susie loved it when I finger fucked her, and she soon came. One last kiss and then I left.

As I drove home, I wondered if Susie's folks could smell her cunt juices after our finger fuck. Perhaps they were realistic enough to know that if they wanted her to find a husband, then she would have to give potential suitors a 'test drive'. Or perhaps they realised that teenage girls get horny, and their needs have to be taken care of. Well, I have no plans for matrimony with Susie or anyone else, but I did hope that I might get a 'test fuck' one day.

And then I thought about Angela and her fascinating mouth, and I wondered how I could get that mouth wrapped around my cock.

Wednesday

It was my cousin Chrissie's eighteenth birthday. A large party was planned for her the following Friday, but there was a small family gathering held tonight, which my parents and myself attended.

I like Chrissie. She is always a lot of fun, and she always hugs me. Over the last few years I had especially enjoyed the hugs as I was conscious of Chrissie's boobs developing. Now she has become a beautiful, sexy girl. I often wish that we weren't related, so that I could date her and fuck her.

There were mostly adults at the party, but about halfway through the evening, Chrissie came and took my hand. "Come with me," she whispered. She led me into the kitchen, and then into the laundry room, and closed the door.

"I want a birthday kiss," she said. Well, there's no harm in that, I thought, so I leaned down and kissed her lips. Chrissie's mouth locked onto my lips, and then her tongue found mine. I was surprised, but I responded, and suddenly the word 'cousin' held no meaning for me.

We kissed for a long time, and when we broke off, Chrissie was all flushed and excited. "I've wanted to do that for such a long time," she gasped.

We held each other until our breathing returned to normal. Chrissie turned to leave. "And you know what else I've been thinking about?" she said. And before I could answer, she said "How much I want to fuck you. Not tonight, obviously, but soon."

I didn't say much to my parents on the trip home - my mind was too busy thinking about Chrissie and her fabulous tits. I need a plan!

Thursday

I was walking up the stairs at work, when I heard female voices above me. I looked up, and I do mean UP - right up the skirt of a white uniform! And right there was an incredible sight - a beautiful shaved pussy! I stared for a few seconds and then moved on, saying 'Hi' to the two girls who were chatting on the stairs. So the bald pussy belongs to Jill, I discovered. And Jill doesn't wear panties to work. Interesting!

I wonder how I could get to check out her bald pussy a little closer.

Friday

It was the night of Chrissie's 'real' party. Susie and I had both been invited, of course, but I knew that Susie couldn't go to the party. Her parents have this weird rule, that the family stayed together on Friday evenings. It was something to do with religion - I was smart enough not to ask questions.

Susie felt bad for me that I had to go to the party alone, so she suggested that I should invite her new BFF, Angela. I feigned reluctance as I accepted Angela's number from Susie.

Angela eagerly accepted my invitation, and she looked stunning when I picked her up. I had to fight off other boys all evening.

Chrissie was a little snarky about me being with such a hot girl. But I calmed her down by saying that Susie had insisted, as Angela was new to our town and hadn't made many friends yet.

Then I had a brilliant idea. The weather forecast was for a hot sunny day tomorrow, ideal beach weather. I loved the beach, but Susie had very fair skin and she burnt easily, so she wouldn't go to the beach with me. Not that I really minded - there were always plenty of bikini-clad distractions there for me to enjoy. So I invited Chrissie to go to the beach with me tomorrow, and she happily agreed.

When I took Angela home after the party, I went to give her a kiss on the cheek. But she grabbed my head and locked lips with me. "Thanks for taking me to the party, Tim," she gasped. Then she added "you're a good kisser. Susie's a lucky girl."

Saturday

It was a glorious sunny day today, ideal beach weather. I told Susie that I was going to the beach, but I forgot to mention that Chrissie was going with me.

We had fun in the water, and I managed to 'accidently' bump into Chrissie a couple of times. We tumbled around in the water, and I 'accidently' grabbed her boobs a couple of times. Each time she giggled. Then we lay on our towels in the sun to dry off. Chrissie asked me to put some sunscreen on her back. She undid the strap to her bikini top, and she moaned when I rubbed her back. I was just thinking about slipping my hands around her tits when a familiar voice said "Hi, Timmie". I looked up and there was Angela. "Who's your friend?" she asked.

Chrissie reached around and fastened her bikini strap, and then rolled over. "Oh, it's your cousin Chrissie," said Angela, surprised. "For a minute there, I thought that you were cheating on Susie."

"I can't cheat on Susie with my cousin now, can I?" I said.

"No of course not," replied Angela.

"Join us," invited Chrissie.

"Thanks, but my friend is over there," said Angela. "I had better go and sit with her. Bye now."

I watched Angela walk away. Damn, she has a nice ass, I thought. And that hot pink bikini ...

Chrissie punched me on the arm. "You have a girlfriend, mister," she said. And then she whispered "Not to mention a horny cousin who wants to fuck you. It's not cheating if we fuck. It's not as though I could be your girlfriend in public."

We both lay on our tummies, and Chrissie wriggled over close to me. "Feel how wet I am for you," she whispered. She lifted her hips a little and I slid my hand under her, and into her bikini bottom. Much to my surprise I found that Chrissie was fully shaved, and she was very wet. "You like?" she whispered. "I like very much," I said, memories of Jill's bare pussy floating through my brain. I knew that I had to find a way to fuck Chrissie, and soon.

I got a little sunburnt at the beach, so I told Susie that we couldn't go out tonight. She seemed a little put out.

Sunday

Church with Susie and her family as usual. After church, Susie and I chatted with Angela. I was a little apprehensive about what Angela might tell Susie, but she didn't mention the party or the beach.

I told the girls about a movie that I wanted to see. Angela was keen to see the movie, but Susie wasn't, and she suggested that Angela and I should go to the movies together. "Just so long as it's not next Saturday," she said. Because of Susie's odd family rule about Friday evenings, Angela and I agreed that we would go to the movies next Friday.

Monday

Jill was working in a room next to our laboratory, looking up test results from our records to put in test certificates for customers. I was helping her - she was sitting at a desk, and I was standing next to her. Then I reached across to point out something, and my hand brushed across her arm.

I felt like I had been electrocuted! Ten thousand volts at least! I couldn't move, and my mouth had forgotten how to talk. And it was obvious that Jill felt the same.

I took her hand, pulled her to her feet, and led her into a storeroom next to the lab. I locked the door and she pounced on me, kissing me eagerly. I squeezed her ass and then I couldn't wait any longer. I bent her over a desk and lifted up her dress, exposing her beautiful smooth pussy to my sight. I ripped down my pants and rammed my cock into her eager wet cunt. And we fucked - there is no other word for it. And fucked. And fucked.

I know that Jill is married, and that what we did would be a one-time thing only. I am envious of her husband who gets to fuck her every night.

Tuesday

TV night at Susie's house as usual. Susie wore a pair of very short, tight shorts. I was sure that I could see a very slight cameltoe showing through. I must admit that Susie has very nice legs.

When it was time to leave and Susie walked me out, she asked if we could go and sit in my car this time. I could tell that she was horny and wanted more than her usual quick cum.

As soon as we were in my car, Susie pounced on me, kissing me fiercely. Then she unzipped her shorts, and pulled them and her panties down to her ankles. Although her pussy wasn't shaved, I could still make out her pussy lips in the moonlight. I decided to try something different. I bent down and licked her pussy. She let out a little yelp of surprise, grabbing my head and pulling my mouth hard against her pussy. She bucked and moaned, and then came harder than I have ever seen her cum before.

When Susie had recovered, she gave me a final kiss and said that she had to go. As I drove home, I replayed Susie's orgasm in my head. I think that sweet little Susie might be just about ready to meet Mr Cock.

Wednesday

University all day - nothing worth recording.

Thursday

I had been asked to work afternoon shift on Friday to cover for the usual staff member who was ill, so Angela and I had changed our movie night to Thursday. I rarely saw Susie on Thursdays, so it made no difference to her.

The movie was at the drive-in. Angela was wearing a light top, with clearly no bra, and a very short skirt. As soon as the movie started, I leaned over and kissed her. She kissed me back, and we tongue wrestled. Then I reached up and squeezed one of her tits. She pushed me away, but then she undid her top and pulled out her tits. She looked so hot in the moonlight.

I sucked her tits, reaching under her skirt and rubbing her pussy with my fingers. Then she reached over and unzipped my shorts. She bent down and took my cock in her mouth, giving me a great head job. She swallowed my cum like a pro.

On the drive home, I didn't think about Susie at all.

Friday

I worked afternoon shift today from 3pm to 11pm - at least in theory! It had been a busy shift and I was tired, waiting for the night shift guy to relieve me. I was getting annoyed at his lateness, and he finally arrived at about 11:30.

It turned out that the reason that he was late, was that he had been on a date, and he had got laid for the first time! And he wanted to tell me all about it!

All that I wanted to do was to go home and get some sleep.

Saturday

It was early evening as I sat alone in the shed, listening to the yells and laughter of my friends playing tennis. This was a church Youth Club event. There were two doubles games in progress, and I was the one who had missed out playing this round.

Earlier today, Chrissie had called and invited me to go tenpin bowling with some of her friends, but I had already promised Susie that I would play tennis with her.

I thought about Susie and Chrissie, and then suddenly I had a moment of absolute clarity. Susie likes it when I rub her pussy, but she is never going to let me fuck her, I realised. On the other hand, Chrissie is practically handing it to me on a plate.

So what the hell am I doing here, I asked myself.

I picked up my car keys, got into my car, and left. I knew that Susie and her sisters could easily walk home, as their house was nearby.

The bowling centre was only about ten minutes' drive away. When I walked in, I saw Chrissie, along with three other girls, and a boy who looked to be a little older than me. I had a moment of panic, thinking that he might be Chrissie's date, but it turned out that he was with one of the other girls.

I joined them for a game of bowling, and then we decided to go into the city for coffee. Chrissie told the others that she would ride with me. We chatted easily during the trip, and Chrissie said she was happy that I had joined them.

After coffee, I set out to drive Chrissie home. "It's such a beautiful night," she said, "Let's go for a walk along the beach."

I drove to the beach, and as we parked, Chrissie noticed a bright light over the ocean. "Oh, look how bright that star is," she exclaimed.

"That's Venus, Goddess of love," I said.

"Is she also the Goddess of casual sex? "asked Chrissie.

"Probably," I replied.

We took off our shoes and I grabbed a blanket from the back seat, and we walked along the sand, until we found a secluded spot. "Let's stop here," I suggested.

I spread the blanket on the sand. Chrissie immediately slipped out of her shorts and panties, and then she took off her top. She lay down on her back, and the moonlight lit up her amazing tits and smooth shaved pussy Then she opened her legs and stroked her pussy. "Come and fuck me," she said invitingly. "I'm so horny. I want your big cock inside me right now."

There was no foreplay. My cock was rock hard, and Chrissie squealed as I rammed my cock into her eager cunt. Her cunt was amazing - tight, but not too tight - just right! She moaned and bucked, thrusting her hips up to meet my thrusts. "Oh, your cock feels so good in my cunt," she moaned. "Just as I imagined it would. Ohhhh, I'm cumming!!" And with a final thrust, I filled her with my cum.

We cuddled for a while, and I enjoyed the feel of her tits against my chest. Then we decided that it was time to leave, so we dressed and walked back to my car.

I drove Chrissie to her house, and then as I drove home, I thought about her amazing cunt, and how I wanted to get some more of it.

Sunday

I called Susie and apologised for leaving last night - I said that I was ill. And I told her that I was not going to Church today as I still felt ill.

I wanted to clear my head, so I went up to my favourite place of solitude in the mountains. Sitting on the edge of the escarpment, with the panorama of the city spread out before me, and with only birdsong for company, I was able to think clearly. In my mind I wrestled with Susie and Chrissie, with occasional thoughts of Angela intruding. I knew that Susie would never let me fuck her, but that there was an excellent chance of enjoying Chrissie's tight cunt again in the future, at least until she found a boyfriend. And so I decided that I would break up with Susie.

Monday

At work, I wrestled a lot with the whole Susie-Chrissie question, but at the end of the day I hadn't changed my mind. I will break up with Susie tomorrow night. She will be hurt, sure, but prolonging things would only hurt her more

Tuesday

When I arrived at Susie's house, instead of settling in to watch TV, I asked her to come down to my car. There I broke the news to her. She burst into tears, and ran back to the house, crying.

As I drove home, a part of me felt like the lowest form of life on the planet, but another part of me felt immense freedom.

Wednesday

Attended lectures all morning as usual - Maths, Physics, Engineering. Blah,blah!

At lunchtime I drove over to the Teacher's College to see Chrissie. When I found her, she was with the same three girls that I had met on Saturday. We all chatted for a while, and then one of the girls, Holly, invited us all to a party on Saturday. We all agreed to go.

Thursday

Nothing of interest to report.

Friday

I called Chrissie to make arrangements about the party.

"Are you coming as my cousin, or as my date?" she asked.

"Your friends don't know that we are related, do they?" I asked.

"No," said Chrissie.

"Then I'll go as your date," I replied. "Could be more fun."

"Cool. Pick me up at eight," she said.

Saturday

I picked up Chrissie at eight pm and we went to the party.

As soon as we were inside the house, Chrissie took off her coat. Underneath she was wearing what could only be described as a 'slut dress'. It ended about two inches below her pussy. And quite a lot of her boobs were on show as well. "What?" was all Chrissie said as I stared at her.

Through the evening I stayed sober, but not so Chrissie. I saw her dancing with one boy with her tongue down his throat. Then they disappeared into one of the bedrooms.

Holly came up to me. "Looks like you've been dumped," she said. "Looks like it," I replied. "I could help you feel better if you like," she whispered seductively. "I like," I replied.

All the bedrooms were occupied, so I led Holly out to my car. As soon as we were inside my car, she attacked me, locking lips with me, and grinding her tits against my chest. Then she pulled out my cock and took it in her mouth, sucking expertly, and swallowing all my cum. I briefly thought that she was almost as good as Angela - almost, but not quite.

We returned to the party. Holly wrote her number on a piece of paper and gave it to me. "Call me," she said. "I can do other stuff too."

Chrissie was a real mess, so I decided to take her home. Her parents were less than impressed by her drunken condition, especially since we had forgotten her coat, and so they had their first sight of the 'slut dress'. And then they blamed ME for letting her get drunk. Parents!

Sunday

I had a call from a still-hungover Chrissie, apologising for her behaviour. "I'll make it up to you, I promise," she said. I'll see that you do, I thought.

Later I had a call from Angela. "I'm just calling to see how you are, without Susie," she said. "You know, Susie's not really my best friend. If you ask me out sometime, I might say yes."

Then I thought of Holly's number in my pocket. I had heard of love triangles, but this is a love square! Good grief!

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousalmost 4 years ago
Young lust

Great diary. Reminded me of my younger years had three girlfriends but never thought about them living near each other. That got me on the hunt again to find one.

Share this Story

Similar Stories

Time Stop Inheritance Ch. 01 An elderly man engages the services of his neighbor.in NonConsent/Reluctance
Halloween will Never be the Same Ouija board releases something evil ... and dirty.in Erotic Horror
A Classmate's Mother Shy university student is seduced by his friend’s mom.in Mature
The Dream Life Ch. 01 18 year old virgin (me) gets seduced by my friend's mother.in Mature
Going Where No One has Gone Before A male virgin plumbs the depths of a sexually starved milf.in Mature
More Stories