Summer Vacation

Story Info
Since we turned 18, we decided to lose our virginity.
5.6k words
3.5
36.7k
13
5
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
barkirk
barkirk
3,070 Followers

Growing up, my family had a place in Vermont right on Lake Champlain that was very remote. The drive back in to the cabin was a mile long through the woods. We also had a mile of lakefront where we could do whatever we wanted away from any other people sailing, swimming, diving, skinny dipping, sailing...etc.. Spending every summer there growing up was heaven. The cabin was a very old three story shell built around the turn of the century. The furnishings were sparse and old and the beds were thin mattresses over metal coils.

In high school I started dating Debbie who had no experience with guys, but had a body like a playmate. 5'7" with a very narrow waist and breasts that just invited you to suck on them. I (Steve) was not exactly the Charles Atlas type, but 5' 11", 155 in very good shape. The problem was, we were both virgins and she wanted to wait until she was married to lose it. So I had to be happy with the frequent hand jobs, though I was not allowed to reciprocate as she did not want me to even touch her.

The summer after we graduated, I asked Debbie if she would like to spend a few weeks at the cabin and she jumped at it as she had heard so much about it. I also thought it would be a fun place to celebrate her recent 18th birthday, little did I know how fun. As we were driving up we were talking about all the things we could do there and she asked about skinny dipping. I told her there was no feeling in the world to match it. The water caresses your whole body and you feel so free. Debbie said that we would have to try that as she had never done anything like that. The thought of finally seeing her out of a bathing suit and fully naked instantly gave me a throbbing erection which Debbie was quick to pick up on. It was uncomfortable driving with my dick aching to get free of my pant leg and Debbie wasn't helping by reaching over and stroking it through the pants. Her fingers kept pressing into the engorged head and gently squeezing it, then sliding her hand down the shaft as if feeling the size and length. I had to pull her hand away as I was on the verge of cumming in my pants and I was not thrilled with having a wet spot on my pants the rest of the drive.

"What's wrong, Steve?" she asked "Didn't you like that?"

"You had me ready to cum and I'm not sure how my pants would look at the next rest stop."

"There are ways around that." and she reached over, unzipped my pants and painfully fished out my very stiff cock until it was completely free.

"Oh, man, that feels much better," I said "it sure hurt down my leg like that." Debbie spit on her hand and proceeded to slide it up and down the shaft very slowly, spending most of the time caressing the head gathering the pre-cum at the same time. Every time I got close to cumming, she stopped, telling me to hold off. I have to say that I could have driven past Vermont into Canada with the attention I was paying to the road, but I have never wanted to cum more than right then. Then Debbie took off her tee shirt so she was just sitting in her very thin, see-through bra. This was a first for me. Even though I had seen her in a bikini, I never saw her in her underwear nor seen her nipples and this was in incredible turn on. I was very aware of the fleshy mounds and how much more there was hidden by the thin material. As soon as she touched my dick again, I started shooting cum all over myself. In fact, a glob landed right on the windshield.

"Now I know what it takes to really get you off." She said. "I should have done this earlier."

I had to pull off the highway to clean myself up and the get my pants zipped up and I asked her if she was going to put her tee shirt back on.

"I don't think so, " she replied "I like to thought of getting you excited again."

"Even if it means we get in a car wreck?" I asked?

"This will teach you how to concentrate and focus on driving, think how valuable a skill like that can be."

Yeah, I thought. Just the type of skill I need, the ability to focus on something else than her body....

We pulled back out on the highway and I had little luck ignoring her sheer bra with her nipples poking through half an inch. It wasn't long before she put her head back and dozed off making her chest stick out farther. I was noticing the trucks and cars driving by were very interested in her display and I was finding it hard to finish passing other vehicles. After a bit she opened her eyes and looked out at a truck that had been keeping pace with us. She immediately covered her breasts with her arms and yelled at me for not saying anything.

"Hey, you were the one to take your tee shirt off, did you think no one else would notice? And why bother covering up at this point, they have already gotten an eyeful."

"I see you recovered from earlier," she said, noticing the tent in my pants "I thought you were going to work on focusing on the road?"

"Perhaps with more time I can become and expert at it, but a skill like this takes a lot of practice." I replied.

Just then, the trucker honked was signaling something.

"What is he doing?" I asked Debbie.

"I think he wants to see my tits."

"Go ahead," I said "though I am not sure I want to be next to a trucker trying to get himself off while driving."

Debbie turned her back to me, reached around behind her and unclasped her bra. She then put her arms over her head and rotated her torso. I could see her tits bouncing back and forth from behind her. I was instantly struck with jealousy that the first guy to see her tits was a complete stranger and not me. "OK. Now you have to turn around so I can see them." I said.

"Not a chance," she said and slipped her bra back on "you will have to wait to see more."

"Not even a peek?"

"Nope, though I will let you rub me a bit." As she slipped off her shorts. She leaned back and put her feet spread apart on the dashboard. I took my eyes off the road and stared at the cloth covered mound with the dark patch of hair showing through. The truck driver honked again, but I ignored him as I reached over and felt her moist panties over her slit for the first time. It could not have been more than 30 seconds before she was screaming out her first orgasm I'd seen her have. I stopped rubbing, but she immediately grabbed my wrist and put my hand back on her wet pussy.

"Don't stop, please don't stop until I say."

My fingers started stroking her moist flesh and I noticed that her breathing became much deeper with I hit the nub on top of her slit, so I started concentrating on that alone. She pulled my hand away.

"That is too much, go easy on my clit. Spent time around it and hit it periodically - that would be a lot better."

I drove the next 30 miles stroking her pussy and every time I tried to get under her panties, she stopped me, but I am sure she came 3-4 times, each time screaming out her ecstasy. Finally, with the muscles in my arm cramping up, she told me to stop. Apparently the trucker got tired of trying to watch while driving and disappeared, replaced by another driver in a pickup truck. Debbie looked over at him and smiled. Again, she turned her back to me -- removed her bra and shook her tits at him. Then she knelt of the seat, still facing out the window, pulled down her panties and spread her knees apart. I could see her arm moving like she was playing with herself. Her other hand was apparently playing with her nipples. At least she was letting me see her ass for the first time. It was gorgeous, tight, firm looking, round. I reached over and squeezed her ass cheeks. I've never felt my cock that hard before and I thought it would rip through my shorts. I knew if I touched myself I would cum right there in my pants.

"OK," I said, "that's enough! You are showing strangers things I've never seen. Turn around."

"No way, I like keeping you in suspense." And she stayed facing the pickup truck driver. I heard her squeal and looked over and saw the truck driver had lifted up his hips by arching his back so Debbie could see his huge cock.

"You have got to be kidding," she said "no way can that thing be real!"

I definitely saw that it was and it had to be half again the length of my six inches. Debbie was now furiously rubbing her pussy and I could hear that she was very wet. The driver of the truck grabbed his dick and was pulling on it, extending it farther into view which made Debbie groan and rub her pussy even harder. I was thinking about how I had to be gentle around her clit, but I guess that doesn't always apply. Debbie let out a yell, panting heavily and collapsed face first against the door. After a few minutes she raised herself up, pulled up her panties and put her bra on before turning back to me. Then she put her tee shirt and shorts back on.

"I need a bit of release myself now." I said, unzipping my pants. "That was so hot."

Debbie shocked me by leaning over and dropping her mouth right on my disk. I could never even get her to kiss it before now. It felt like heaven getting my first blowjob, feeling her hot silky smooth mouth taking in most of my cock. Within a minute I told her I was going to blow, but she started sucking harder. As soon as the first shot entered her mouth I felt her swallow. I must have dumped a quarter cup of cum down her throat before I was done. Amazingly I was able to stay on the road in my own lane.

"Why did you swallow? I warned you that I was about to cum."

"I thought that was what I was supposed to do." Debbie replied. "Did I do it wrong?"

"No, you did it right, believe me."

Debbie then asked how much farther. I told her 4 hours or so, so she said she needed sleep and curled up and slept the rest of the trip.

We arrived at the cabin at around 10 PM and by the time we had unloaded the car, unpacked and gotten basically set up, we were exhausted and went right to sleep.

The next morning, after breakfast, Debbie wanted a tour of the place. We put on our bathing suits and walked down to the beach which was secluded and all to ourselves, except when the motor boaters came over for swimming or picnics. Then we walked up into the woods until we came out into the cove with the flat granite ledge which was very secluded. I told her this was where we skinny dipped as we would have plenty of warning is boats came in. I proceeded to strip off my swim suit, watching to see if she would follow my lead. She hesitated, then reached behind her releasing those incredible breasts for me to see the first time. I could sense her eyes staring at me to see my reaction, then slid her bikini bottoms off her hips slowly and let them fall to the rocks. I guess she could tell by my dick pointing at the sky that I liked what I saw.

"Finally!" I gasped. "You had me going nuts with your teasing yesterday. You are sexier than I imagined."

With that, she turned and knifed into the water. When she emerged, she laughed and said "This is incredible. It is like a million fingers all over my body."

"I wish I were the water doing that to you" I replied, and dove in after her.

We spent the next 20 minutes chasing each other, grabbing different body parts getting more and more excited. Debbie started hugging me in the water and grinding her pussy against my aching cock and said "Perhaps we don't need to wait until we are married." We were on the towels on the rocks in seconds and for the first time I was sucking on the eraser size nipples feeling her body writhe and twist underneath me. I slowly kissed down her tight stomach, spending time on her navel as this got a good response out of her. I had to get a close look at her pussy though, so I continued kissing down between her legs. I lifted my head up and saw for the first time this nice tight pussy. I just had to taste it so I lowered my head down and ran my tongue up her wet slit, savoring the tangy flavor of her pussy. When I got to her clit she gasped and grabbed my head with both hands and held my mouth right over the hard nub. My tongue kept flicking over it while she ground her pubic bone into my face. My face was getting soaked with her juices, but I kept at it until she had two orgasms. When I jabbed my tongue into her wet hole, she came a third time.

I lifted my head up, "Was that good? Are you ready for the next course?"

"Yes," she said still panting from the last orgasm, "get up here."

My cock was ready to explode, so I crawled up so I was poised ready to fuck her for the first time. Her hand reached down and started pulling and stroking on my extremely hard cock and guided it towards her virgin hole. I felt the incredible feeling of my penis spread the lips of her vagina then the head slipping inside. Man, this was going to be great.

"Oooooh," Debbie moaned "push it all the way in."

I was just about to thrust in anticipating her cherry when we heard the sound of a motor out on the lake. I tried to tell her that they were probably just passing by, but she abruptly pushed me off, jumped up and pulled on her bikini. I reluctantly put on my suit also. Talk about frustration. I wanted to drag her into the woods where we could be alone so I could finish what we started, but we had out gear laid out all over the rocks and didn't want to leave them out if the boaters came into our cove.

We sat there staring out onto the lake watching a monster cabin cruiser coast towards the rocky ledge and noticed 4 20 something guys staring back at us.

"Ahoy, there on the rocks. Do you mind sharing this cove?"

I was about to yell back that we would mind, when Debbie beat me to the response.

"Not at all, there is plenty of room here for all."

I glared at her, but she was oblivious, staring out at the boat drifting in. The men on the boat dropped anchor, dove in and swan to the rocks. When they came up out of the water, I could see Debbie checking out the lightweight swim suits clinging to their crotches. They did not seem to be bashful about how revealing they were and Debbie did not mind overtly staring. I have to say that these guys must have been packing serious meat under the swim suits. I nudged her and she looked over at me and smiled.

"I love the scenery around here. It is so inspiring."

The guys flopped down on the rocks sitting as close to Debbie as they could and introduced themselves. Mike was a 2nd year law student at Yale; Brian was an engineer working for the city of New York; CJ was the oldest at 30 and he owned his own development company in New London. Tom didn't do much of anything as he inherited a ton of money and just liked to have fun. The boat was his and the four of them were out on a 2 month cruise from NYC to the northern tip of Lake Champlain. All 4 looked as though they spent a lot of time in the gym. They turned the conversation around and started asking her questions about where she was from, how old she was (their eyebrows raised when she mentioned she just turned 18), where she planned to go to school, etc.. She was sucking up the attention and not unaware that they were scanning up and down her body. Subconsciously or consciously, she leaned back with her arms straight behind her which made her breasts push straight out. This definitely got a rise out of the guys who shifted themselves while talking to her, so they could take in her sensual beauty.

I was just a spectator watching the sharks circling around for the kill. When I attempted to introduce a new topic, I was greeted with one word answers and the focus shifted back to Debbie. I was feeling more and more jealousy and was not sure where this was going to lead since Debbie was newly aware of the incredible affect that her body has on men. I saw her glance down periodically at the growing bulges in the swim suits arrayed in front of her. This in turn caused those rock hard nipples to push against the bikini top quite obviously. I knew I had to get her away from these guys as I could see where this was leading, so I stood up and told Debbie that we have to get into town for groceries for dinner. She hesitated and then sat back up, saying "Well guys, it's been fun, but we have to go."

One of the guys (Mike, I think) asked what we were planning on for dinner mentioning that all they have had the last few weeks is Dinty Moore stew and Spam.

Debbie immediately asked if they wanted to join us back at the cabin as we were having spaghetti. They all agreed to this at once and after directions swam back to their boat to get changed while we walked back through the woods.

"Deb," I said "I was hoping we could finish what we started this evening, but if we invite over a bunch of guys it will turn into a party. I really would like to have some time alone with you."

"We'll have plenty of time alone as this is just the first night here and these are great guys." Debbie responded.

I thought about saying -- yeah, for you as they would jump you in a flash -- but bit my tongue.

There was no time to do much else as the stores were closing and we really did need supplies, so we got back to the cabin, pulled on shorts and tee shirts, got in the car and drove off, leaving the cabin unlocked for the guys, if they got there before we got back.

When we arrived back at the cabin, the guys had arrived and were sitting out front drinking beers from the cooler they hauled up. They were more than helpful carrying the groceries in and getting everything put away. They even helped with the cooking. After a great dinner, all the guys dove in and did all the dishes while Debbie and I pretty much watched. When everything was cleaned up we were all sitting around in the living room relaxing and I was starting to get used to the conversation as these were bright educated guys. They offered beers to Debbie and me which we accepted, even though we were under age. I was not sure I liked the taste, but nursed it anyhow.

Brian asked if we had cards, if so we could play poker. We did have cards, but I said I had not played much and I was sure that the stakes would be way too high for me. Debbie said she doesn't play cards at all but would be happy to watch. CJ said "No big deal. Even penny ante poker is fun."

"I can handle that if you're sure that would not be too boring."

"Not at all," Brian responded "we are so competitive that anything would be heavily contested."

The game went along with no one really winning all the pots when Tom turned to Debbie and asked if she was still wearing her bathing suit under her clothes.

"Sure, we just pulled street clothes on over the suits as they were already dry by the time we got back."

"Wouldn't you be more comfortable if you at least took off the bikini top?"

"I am not undressing in front of you guys." Debbie shot back.

"I didn't mean that. I meant removing your bikini top and sliding it out the arm hole like girls do. I just think you look uncomfortable."

"Alright," Debbie said "I can do that."

With that she now had the rapt attention of the entire table as we were all turned to watch this. Debbie reached behind her, then slid the shoulder straps over her arm, then pulled the top out of the other arm hole. I am not sure she was aware of this, but her tee shirt was quite see through and we were all treated to her dark areolas showing. When she looked down and saw this her hands immediately went over her breasts covering them.

"C'mon, don't cover something that beautiful up," said Tom.

Debbie looked doubtful, but dropped her hands down so we could see that not only was the shirt see through, but her nipples were now poking out a quarter inch. I cannot speak for the rest of the guys, but my shorts were starting to feel a bit tight.

"Man, you are knockout." CJ said, "I'll bet you are unbelievable in bed."

"Um, thanks, but we still have not gotten there," she said, "this was going to be the week that it happened.

"You two are virgins?" Carl asked?

barkirk
barkirk
3,070 Followers
12