the-posse
FIRST TIME SEX STORIES

The Posse

The Posse

by defcon4
20 min read
4.57 (6200 views)
adultfiction

The Posse

Β© By Defcon4 2025

Anybody mentioned in this story, even thinking about doing anything sexual is over the age of 18.

Note: For the most part this was self-edited so expect there will be some mistakes.

Enjoy the adventure!

Yes, I am part of a Posse, and I have been for years. We initially called ourselves the Valley View Verve or V3 for short. We all met in the 3rd and 4th grade when our families moved into a brand-new neighborhood, Valley View. The neighborhood sits a couple miles out of town across the Susquehanna River from downtown, carefully carved out of the surrounding forest and farmland. Eventually we dropped the V3, and we became simply 'The Posse'. By now that is how we were referring to by almost the whole town.

There are currently 3 girls, Ana, Ella, and me, Cary and two guys, Jon and Andy, in our Posse. John and Andy are cousins. Their fathers are brothers and started an engineering firm in town after finishing Grad School. Interestingly their mothers are also sisters. Cousins

2

is that a thing?

There have been others that were part of the Posse over time. Some moved out of town, some left due to some perceived slight, and some ended up connected with other affinity groups, football players, theatre folks, whatever.

The 5 of us were the founding members and as time went on, I think it became harder for others to fit into the group given how long we had known each other, but we were always welcoming to those that wanted to try. Ana is our unelected leader of the Posse. Over time she just sorta evolved into it. Not that any of the rest of us minded she usually had good ideas that kept us all entertained.

When we were younger her entertainment usually involved doing something outside. Bike riding, sledding in the winter, hiking around the surrounding area. We build a fort about a 1/4 mile behind our neighborhood out of dead trees and building materials we scrounged from our parents houses. It eventually became our clubhouse as we grew out of playing cowboys and Indians.

In a way we evolved into our own affinity group. We were basically 5 kids that did well in school, were involved in some school/external activities but not dedicated to any, we were all reasonably attractive and mostly stayed out of trouble. Ana had played piano, it seemed like her whole life. She filled in playing at church when the primary person was unavailable and helped out at elementary and middle school concerts. Ella ran track and cross country. I think she could have excelled at running if she chose to do so. She had a natural grace to her running style and the determination needed to strive for success. Unfortunately, that wasn't where her heart was and she basically admitted to me that she did it to stay in shape and for the camaraderie Jon played on our HS golf team and had a few D3 offered to play in college. As he put it his golf game was destined to carry him all the way to being the men's champion at our local country club, and that was about it. His main focus like Andy's, was engineering. For his part Andy played defense on our region's Junior A hockey team, he was considering trying to walk on in college but wanted to see how much free time he had when he got there. And me, I had done gymnastics up until I was 16 when a series of injuries sidelined me for a year and at that point it didn't seem to be worth the effort to try and work my way back.

I guess because we all have been friends for so long dating between any of us never really became an issue. We hung out together all the time, but it had always been very platonic. Sure, at times we were all fill in dates for family weddings, or homecoming dances and proms, and the like but that was the extent of it.

Now would probably be a good time to describe 'The Posse'. Ana has Greek/Italian bloodlines from which she derives her classic Mediterranean skin color. She is 5'6" tall with thick brown shoulder length hair, she weighs 135 lbs. or so. Her breasts we a solid B cup and she has a bit of a bubble butt. Ella is a bit taller than Ana is at 5'8" and she has the topical runners' body, tall and lean, with long legs. Her mother is from the West Indies and met her dad when she came to the US as an exchange student in high school. Her skin was almost flawless, and its color was this wonderful shade of light mocha. She weighs about the same as Ana despite being 2 inches taller. She is probably the prettiest of all the girls but at the same time not as curvy as Ana or me. She complains that she is totally flat chested, but I think she really is a full A.

Jon & Andy are interesting in spite of the fact that both their parents are siblings, aside from some facial features, there are almost no physical similarities. Andy took more after his dad's side of the family. He was a big tree of a guy 6'2" and a lean 205 lbs. If any of us had any bullying issues growing up Andy was quick to put an end to them. While I don't believe that he ever got into a real fight in school he had the demeanor of someone that would be happy to oblige if called upon. What most people didn't know was that he was really more like a gentle giant. He had short curly brown hair and piercing green eyes. Jon on the other hand seemed to get most of his traits from his mom's genes. He was 5'11" and about 175 lbs. with sandy blond hair, blue eyes, and not an ounce of fat on him anywhere. He looked more like a California surfer than anything else.

The group text from Ana arrived at 10:30 last night asking us all to meet at the clubhouse Friday afternoon, which also happened to be our last day of high school, right after we got home from school. There was a flurry of follow up texts from the rest of us back to Ana trying to figure out what she had in mind but all we got from her was a "You will see on Friday." Reply. When I talked to her the next day at school she was just as tight lipped. So, I guess we will find out on Friday.

When we arrived at the clubhouse Ana was already there. After a few minutes of general chatter between us Ana spoke up. "I have a proposal that I wanted to share with all of you. I do not want an answer today, but I would like you to think it over for the next week. We can all get back together next Friday when you have a chance to agree to it or not. Please feel free to ask any questions that you might have though. Ok?" We all nodded.

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"Ok here is what I would like you all too consider. Come this fall except for Jon and Andy who are headed to the same engineering school in Massachusetts the rest of us are all headed in different direction, so this is probably our last summer as the Posse." Looking around at the others I could see in their faces that we were all wondering where this was headed.

She continued. "While none of us have had a serious relationship in high school I know we have all been on dates and without getting too specific have all had some experience with the opposite sex. However, I don't think any of us can say they have had a lot of experience. I would like to propose that over the course of the summer we work to change that issue. I, for one, do not want to head off to college without having more sexual experience under my belt." Looking around at the others I think it was starting to dawn on us where this was headed.

"So, I would propose that we use this summer to help us all gain more sexual experience in preparation for heading off to college. Look, we all like each other and we certainly trust each other. After all these years of friendship I don't think that there is a risk of any of us reading more into any potential physical activity than is intended. Look, I love all you guys so don't be mad at the suggestion. Everybody is free to say no all I ask is that you give it serious consideration, please." At which point Ana sat down.

"So essentially what you are proposing is we create sort of a mini-Tinder app among the 5 of us.?" asked Ella. "I hadn't really thought of it that way but yes." Replied Ana. "How would it work?" Asked Jon. "Well, I haven't thought through all the details yet, but I was thinking we keep it simple."

"Say your folks are headed out to a party one Saturday night. You might send a text to the rest of us that says something like is anybody interested in hanging out at my house on Saturday night for a couple of hours. I think keeping it generic enough that if by chance someone sees the text it doesn't raise any flags. At least initially I think that first come first served approach would work best. Remember, in all instances 'No' means 'No'. The person that initiated the text can set the parameters of how far they are willing to go and the person responding has two options. They can agree or they can propose something less than the original proposal. That way both parties get a say in what happens."

I decided to jump into the fray at this point. "So, say that Andy posts a request and I accept it. He would then outline his proposal, say he wants sex, I could either agree or propose say a hand job instead. In which case I assume that he can say no. Is that what you are saying?" "Yes, well with one tweak. I think if you counter the proposal he should accept it. Remember this exercise is about us all gaining experience, some of us are naturally going to come along at a slower pace than others do. So back to your Tinder analogy, once an invite has been accepted there is no 'Swiping Right. Make sense?" Replied Ana.

We all nodded in agreement. "OK a couple other things I think I should add. What happens between the two of you during a rendezvous should stay between the two of you. This is not a contest to see who can get laid the fastest or whatever. We don't need to put pressure on others to keep up. As I said earlier, it is OK if we all go at our own pace. And lastly, we should all feel comfortable that this whole thing is meant to be a learning experience for all of us. Ask questions, ask for help, offer your advice on what feels good and what doesn't. Don't be afraid to try things a bit outside your comfort zone. But again, 'No' means 'No' if at any point in time someone starts to feel pressured to do something they don't want to let me know and we can call the whole thing off."

"I know that was a lot to take in and there are probably things that I overlooked but I think it is at least a solid start. Are there any questions?" There were some follow-up questions for clarification mostly but at least from my perspective it seemed like everybody was considering it.

After a brief pause, she continued. "Ok it seems like You have what you need for now. As I said, if you are interested in at least giving it a shot we will meet at my house next Friday at 8:00 pm. My folks are heading up to visit some old friends for the weekend. If you are coming text me next Friday and I will fill you in on what the plan is for that evening. If you are not interested that is fine, we can keep this stuff separate from our normal interactions so it is not like you will be shunned or something." She concluded with a smile.

With that we all collected our stuff and headed back to our respective houses to get home in time for dinner. It was sure going to be an interesting week.

While I was curious what the others were thinking I was all in once I heard the suggestion from Ana. I genuinely liked Jon and Andy, and I felt very comfortable with the proposed format that enabled me to move at my own pace. And I really liked the idea of not being thrown to the wolves when I showed up on campus in the fall.

Not wanting to appear too eager I did wait until noon on Friday to text Ana to confirm my attendance.

Me: Ana I'm in, I am clearly a bit nervous, but I am committed. While I am not sure how far I am willing to go I am committed to trying. Thanks for being the one to bring this up. It is a great idea.

Ana: Great welcome aboard. See the next text

Ana: Tonight's format will work like this. To avoid last summer's skinny-dipping debacle, I have proposed the following process to essentially rip the Band-Aid off so to speak to get the whole thing started. Come to the house at 7:45 guys head to the laundry room and girls to my dad's office. Once there, take off all your clothes. At 8:00pm girls you exit the office, leave your clothes there and head down to the basement. At 8:05 guys you do the same, leaving your clothes behind as well. I will already be down there similarly attired. Note I have taken the precaution of removing anything in the basement that might be used as a cover up. Pretty smart, right! I also will have adjusted the temp to ensure we are comfortable. For the rest of the evening, we just hang out like we have done a 1000 times before. I will have snacks and such for us down there. We can watch a movie, play pool or whatever.

Ana: Girls I suspect that for some part of the evening and maybe the whole time the guys will be sporting an erection. While it will be impossible not to notice I don't think we should make a big deal about it for their sake. Agree?

So, the great skinny-dipping debacle, let me explain. Last summer Ella's parents were taking her two younger brothers to play in a soccer tournament for a weekend. Leaving her alone at the house since she had a summer job. Their house has a pool. Anyway, for like two weeks or so leading up that weekend we were all kidding each other about going skinny-dipping, challenging the others about who would chicken out etc. When the big day came, we all chickened out. It looks like at least those of us that attend will get over that hurdle pretty quickly.

From how she texted it I assume she had that all prewritten and just cut and pasted it to respond to all the replied yes. I wonder if she sent the boys a side note as well. I made a note to ask one of them later.

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Me: I'm still in, I do like your ice breaker. It will surely be a rip the Band-Aid off moment. So, who all is attending tonight?

Ana: You will see when you get here. But I will say that representatives of both sexes have said they will be here. Hopefully no one gets cold feet at the last minute. That was why I threw down the gauntlet with the skinny-dipping comment.

Me: Ok SEE you at 8:00.

Ana: Yes, you will!! And I, you

Well, I guess I didn't need to worry about what to wear tonight but I would obviously have to spend a bit more time on body maintenance than I would on a normal Friday with the posse.

So, after dinner that night I went up to my room to get ready. I showered, shaved all the places that needed shaving, trimmed up those that I didn't shave. Put my hair in a ponytail. Checked myself out in the mirror realizing that this was how others would see me for the next several hours.

A bit more about me. I'm 5'3", 115 lbs., with body complimentary curves in all the right places. I wear a small C cup bra, with a bit of baby fat around my tummy but not bad. As I mentioned I was big in gymnastics when I was younger, think Shawn Johnson, for a mental image. I like my body, no chance if hitting the cover of Sports Illustrated, but that isn't where I would want to be either. And while I was nervous about tonight, I wasn't ashamed to show it to the guys. The girls had all seen each other outer naked over the years many times. But not in a public setting so tonight will be interesting. I threw on some shorts, added a bra, to keep mom from asking questions, a sweatshirt and a pair of flats and headed over to Ana's.

Arriving at Ana's I entered the house through the door we normally used and proceeded to her dad's study. Upon opening the door, I saw Ella had beaten me there and was already half undressed. Joining her I began to remove my sweatshirt and commented. "Well, I guess that means all the girls are in. I wonder if both Jon and Andy accepted." "If not one of them is going to have a busy summer." I added with a smile.

Looking at my phone I saw that it was 7:59. "Well the moment of truth has arrived, ready Ella." To which she simply nodded. I headed to the door, opened it more boldly than I probably felt and without any hesitation I walked out headed toward the basement stairs and started down. As we started down the stairs, I saw Ana standing at the bottom of the stairs and true to her work she too was naked. When we reached the bottom of the stairs, we each got a brief hug from Ana.

Looking around the room it looks like it did any other time we visited here with the one exception being like she said she would she had removed throws that usually adorned the couches and the recliner. While there were clearly other things lying around you could use to cover up, but they would do a poor job and you would look pretty silly trying to do it. And as she had said she clearly had adjusted the heat, so it was not at all uncomfortable down there.

After a couple minutes of chit chat, we head Jon at the top of the stairs announce. "Ready or not here we come." Which got a chuckle from the three of us and which also confirmed that both Jon and Andy had agreed to give the experiment a try. As Ana had predicted when the guys initially came down the stairs they were both sporting pretty impressive erections. Andy's was clearly longer than Jon's by a good inch or so, but Jon's was considerably thicker than Andy's. I thought to myself that this would be an interesting summer.

As they reached the bottom of the stairs unconsciously the three of us immediately focused our attention on their erections, which caused Andy and Jon to instantly turn a bright red. But as requested by Ana we all said nothing and pretty soon our eyes refocused else ware.

What is interesting was that for the first 30 to 45 minutes all eyes were roving constantly across all the interesting areas of the opposite sex. And then, like a switch was turned off, we fell back into our normal patterns. Sure, we continued to look, or at least I did, but now it was more casual. I also noticed that when we first started the girls were especially careful to keep their knees together when they sat or when we bent over to get something making sure there was no one behind them. That too slowly disappeared to the point that I noticed after we had been watching the movie for a bit all three of us girls, were sitting Indian style on the floor. While I would not say that the boys' erections totally subsided, overtime they were a lot less prominent.

I guess that Ana was right we blew right through the initial nervousness and had jumped in with both feet, and naked to boot.

After the movie had ended, Ella was the first to say that while she was really enjoying this evening she probably needed to be heading home. In rapid succession the others concurred. After a brief round of hugs, the first actual boy/girl physical contact of the evening, we all headed up stairs. On the way up I noticed that Jon was right behind me on the stairs, I couldn't help but wonder what he was thinking. Reaching the top of the stairs we returned to assigned rooms and quickly got dressed and headed home.

Thinking about the evening on the walk home, I was very surprised at how casual it turned out. I was also very psyched about the upcoming summer.

The week after the party was pretty normal, we were all getting our summer plans sorted out, we all had some type of summer job that we needed to settle into, so at least for me, there was no mention of the summer experiment in any of my interaction with the Posse. I was starting to think that despite all the bravado; we exhibited at Ana's the other day this might indeed end up like the failed skinny-dipping event.

Then on Tuesday evening of the following week Jon sent out the first text announcing that his parents were headed out of town that weekend and would be away on Sat night was anybody interested in 'Hanging out' which were the code words we all agreed to use to kick off a one of our experimental nights. I read the message a couple times. My plan all along had been to let a couple of the others test the waters so to speak before I jumped in, so I decided to pass even though I was actually free Saturday night. No sooner had I convinced myself that I would pass, both Ana and Ella had replied that they had prior commitments so they could not make it.

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