The Posse

The Posse

© 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. Cousins2 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.

"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.

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.

Oh well, so much for my original plan. I thought it over for a bit and I realized that Jon had taken the first big step, and I really did not want this effort to fizzle out. So, before I thought too much about it, I replied that I was free and would be happy to come by to keep you company for a couple hours. My parents would be home that night so I could not stay out too late.

At this point per our agreed upon rules we took the conversion out of the group text to a 1 on 1 text between Jon and me.

About 15 minutes later I heard the distinctive ping from my phone signaling I just got a text.

Jon: TY I was a bit nervous that no one would accept and that this whole thing might never happen.

Me: To be honest with you that was why I said yes, I didn't want this to not work so despite my initial thinking that I would let the rest of you guys start It up when I saw that it was up to me to make it work it decided to go for it.

Jon: 8:00PM work for you?

Me: Yes.

Jon: The next question is harder, how far do you want to go?

Me: Can we start with just hands below the waist this time?

Jon: Sure, I assume mouths above the waist are, ok?

Me: Yes absolutely, see you then.

Jon: I am looking forward to it! ????

Me: Me too. Night!

Surprised that I wasn't a bit more nervous after that exchange. I went ahead and picked up the first book from my summer reading assignment list and started to work my way through it. Glancing over at the clock beside my bed I noticed that it was now just after 11pm, which was the point I had committed to reading to. I put the book down and got ready for bed.

Our house has a two story traditional design. My mom and dad's bedroom is on the first floor and there are three bedrooms on the second floor. My sister Jen and I had two bedrooms on either side of a Jack n Jill bathroom and the guest room had its own bathroom. My sister is 5 years older than me had had just graduated from nursing school with her BSN and was now working in a big city trauma center near the college she went to in Atlanta. While I did miss her, the fact that we were 5 years apart in age meant that we really did not spend a lot of time together when we were growing up.

What was nice though was that I essentially had the whole second floor of the house to myself. And I intended to use that for my benefit this summer. Toward that end after I went through my evening bedtime rituals in the bathroom, I dumped all my dirty clothes in the hamper and walked out the bathroom door into the hall and down to my room naked. I figured that this was the summer I would push as many of my boundaries as I could, of course, without getting into any real trouble. (Not quite a rebel without a cause was I!).

Saturday rolled around and after dinner with Mom and Dad I headed upstairs and decided that a quick shower and general body maintenance session was in order, so I headed into the bathroom. As was my new habit I left both the bathroom doors open and proceeded to get ready for the evening.

Returning to my room after my shower started thinking "What does one wear to a rendez-vous where the explicit intention is to have sex of some sort?" To not over think it and to keep mom and/or dad from acting suspicious I put on my normal summer attire of yoga pants and a sweatshirt and rather plain white undies. I debated a bit on wearing one of my sexier sets but decided at the end of the day this wasn't a date and I figured that since we only had a couple hours they wouldn't be on long anyway.

I handed downstairs and told mom and dad that I was headed over to Jon's to watch a movie with some of the Posse (not technically a lie) grabbed my purse and headed out to Jon's. He lived on the next street over and half a block down from my house making it only a 5-6 minute walk. On the walk I went through a couple options on how to get this started, figuring since it was our first time we would both be pretty nervous despite having experienced our naked evening a week ago or so. In the end I decided that if Jon didn't take the lead I would.

As I reached the front door and went to ring the doorbell Jon opened the door wearing just a towel. Just as I was about to say something about him jumping in with both feet, he said. "Sorry I was finishing some of the chores that dad had asked me to do, and I lost track of time, I just got out of the shower. If you wait here, I will run upstairs and put some clothes on and I will be right back."

As he turned to head upstairs, I replied, "WAIT! It seems to me the whole plan was to end up naked and try some new things. I am not an expert, but it seems you putting on clothes would be counter to that goal. How about I go upstairs with you, and we take it from there?"

He nodded and we started upstairs together. About 1/2 way there feeling somewhat emboldened I reached over and grabbed the towel from his waist and threw it down the stairs. "Hey, he said that isn't fair." I laughed and said, "Don't worry it will be fair soon enough."

As we entered his room, I did notice that he was at this point sporting quite an erection. Deciding that I was likening this being in charge thing a bit, I maneuvered him over to his bed and quietly suggested that he sit down. As he did, I helped him climb up onto the bed and lie down on his back. As he did, I climbed up onto his bed and got between his legs and gently grabbed his erection with my right hand and began to slowly stroke it.

I should point out that we are now at the limit of my sexual experience. I have been in a similar circumstance exactly one other time in my life and that was in the back of a car in the dark and encumbered by several layers of clothes. So not exactly the same, but close enough that I knew what to do from here.

I did read someplace about the whole CFNM kink and at the time was not sure I understood how that could happen. Given the present circumstances I was starting to see how people could get caught up in that whole scene. It is an interesting power dynamic.

Returning my focus to the task in hand (literally) I began to slowly increase the pace of my stroking; at the same time I moved my left hand between his legs and began to slowly massage his balls. Given his accelerating breathing and the fact that he was becoming quite vocal I was figuring he was getting close to cumming.

Slowing the pace a bit I leaned over and whispering in his ear I asked him if he was ready for me to finish him off. He opened his eyes and asked if I would be willing to take my top off so he could look at me while he came. Figuring that we were going to get there eventually and remembering that I needed to wear these cloths home in a bit and I did not need any suspicious stains on them I decided that it was probably a good idea, so I nodded my head, yes.

Pausing my play I quickly pulled off my sweatshirt and bra and then resumed my stroking. With Jon's eyes clearly focused on my swaying breasts as I brought him closer and closer to the end. I sped up the pace just slightly and within a minute to two he erupted with several impressive blasts which mostly landed on his stomach and chest.

As he came back down to earth he pointed to the top drawer of his nightstand and mentioned that there was a box of Kleenex in there. Smiling as I realized why they were so positioned I opened the drawer and pulled out a hand full and handed then to Jon. While he worked to clean himself up, I quickly headed to the bathroom to wash my hands.

After washing my hands, I figured that it was now my turn, which I was looking forward to, so to avoid any awkwardness when I returned to the room I went ahead and shed the rest of my clothes in the bathroom and neatly folded them and placed them on the counter.

Walking back into the room I noticed Jon's eyes quickly dropped to the newly exposed areas of my body and I saw him break out into a smile. Deciding I want to keep pushing the process along I looked him in his eyes and said, "I think it is my turn now. Can you move over and let me lie down now?" As Jon quickly climbed out of the way I laid back, matching the position Jon was just in, spread legs and all.

"Jon why don't you get between my legs, and we can get started." Not really sure what he knew and didn't know about the female anatomy I went ahead and gave him a two minute refresher course, Taking his hand in mine I showed him around all the important bits, I explained that I like my nipples gently pulled more than twisted, coaching him on how to insert fingers into me as well what I liked being done to my clit when playing (rub all around it but not directly on it). Shaking his head no as I asked him if he had any questions, I laid back on the bed and just relaxed as I suggested to him that he just explore a bit. Closing my eyes I was curious how aggressive he would be in taking the initiative. I shouldn't have worried.

Staring off slowly and a bit tentatively he quickly graduated to alternating sucking on my nipples while he slowly slid his middle finger in and out of me. As he gradually increased the suction on my nipples and the pace of his finger moving in and out, it didn't take long for me to quickly climb the ladder toward my own fireworks.

At this point I moved my hand down to where his was and I took his thumb and directed it to my clit. Taking the hint, he quickly pushed me over the edge. Arching my back, I let out a loud moan when I came. And boy did I. It had to be the best orgasm I had experienced, so far anyway. As I recovered, I caught Jon's eye and said that it was amazing thanking him for the effort. I also shared that it was the best one I had ever experienced which he seemed to take some pride in.

Once I recovered, I moved over on the bed and suggested that John lay down next to me for a bit. Once we were settled in, I shared with him what he did well and suggested a few tweaks for the next time which he really seemed to appreciate. When I asked him how he thought I did I all he could share was that I was a natural and that he would not change anything. While I am not sure I totally believed that it was nice to hear.

As I propped myself up on my elbows I looked over at Jon and noticed that he was fully hard again. Smiling to myself, I looked at the clock on the nightstand and doing some mental math I shared that I shared that I probably had to leave in about an hour to not raise any suspicion with my parents.

Turning to Jon I asked, "Does that timing work for you?" Looking down at his own erection he smiled and nodded in reply. I rolled over on my left side and slid down the bed a bit, while reaching over to wrap my hand around Jon's erection. For a minute I just held it in my hand, and I could feel it pulsing. I then started to slowly stroke it, which elicited a soft moan from Jon.

As I worked to slowly build him up, I got to thinking that I haven't really broken any new ground here today with respect to what I had done to Jon at least so far. After thinking about that for a bit I decided that I was fine pushing my boundaries a bit.

"Jon, I know I offered up hands only below the waist when we talked about boundaries the other day, but I think I am comfortable enough to try giving you a blowjob if that is ok with you?" He simply nodded in response. "Ok but I need you to promise me that you will warn me when you are about to cum." "Of course." He replied.

Figuring there was no turning back at this point I lifted myself up and placed my upper torso on his stomach, I moved my head down and licked the head of his erection. I had been stroking it for a while and he had had been leaking a fair amount of precum, so I got my first real taste of sex in the process.

While the taste was different it wasn't as bad as I feared so I lowered my head a bit more and took the first inch or so into my mouth and closed my lips around it. I had talked to some girlfriends and seen enough on the internet that I knew the basics of what to do and what to expect. So, I slowly began to bob up and down on him while I continued stroking him. Based on the moans I heard from Jon I didn't figure that he was going to last too long.

While I knew that I could get more creative with what I was doing during the blowjob. I was satisfied that I pushed myself and that I was effective in my effort. As if on queue Jon reached down and tapped my head which I took as his signal that he was getting close.

After a couple of final bobs, I sat up and for the 2nd time tonight watched him erupt in my hand. Once again most of it landed on his stomach and chest but some did end up on my hand. Recalling the drill from earlier, I opened the drawer and handed him some tissues while I got up and headed to the bathroom to wash my hands.

As I got to the sink a slightly wicked though popped into my head. There was a medium sized glob of cum on the back of my hand and without too much though I lifted the hand up to my mouth and quickly licked it off. Not sure why I chose this particular time to do it, but I was pretty sure it was something that at some point I would need to taste so I decided now was as good a time as any. While a bit more pungent than the precum I had tasted, I decided that in the end it wasn't that bad. I also decided that I wouldn't share that fact that I did it with Jon.

Seeing the bottom half of my clothes where I left them on the counter I went ahead and slipped them on. While I was horny enough now to want another chance as well to get relief, I knew that there probably wasn't enough time to do so. The last thing I wanted to do the first time I did something like this was to give parents a reason to suspect something.

Walking back into his room I could see the disappointment on my face when he noticed that I was half dressed. "I was hoping that I could return the favor." He shared. "And believe me there is nothing more I would like right but to let you do it, but....." looking at my watch I replied. "I understand, next time I owe you." I finished putting on the rest of my clothes and walked over to the bed and leaned over and kissed him on the cheek. Standing up and taking one final look at his still naked body turned toward and with a final wave I headed home.

Once I got outside and was walking home, I went ahead and checked my messages. I had purposely silenced my phone when I got to Jon's house. Not surprisingly I guess, I saw that I had messages from both Ana and Ella. Quickly deciding I would wait until I got home to reply, I put my phone away and finished my trek home.

I got home just as mom and dad were headed to bed, which was what I was hoping for when I was timing my return out. After a quick good night to mom, I headed upstairs to my room. After I dumped my purse in my room I headed for the bathroom for a quick shower and bedtime prep.

I stripped off my clothes and jumped in the shower, finishing that I dried off and along with brushing my teeth I completed the rest of my nighttime preparation. As I left the bathroom I had a bit of a naughty thought. Instead of turning left toward my bedroom I turned right and headed downstairs to the kitchen to get a bottle of water. Not sure what got into me, but this was the first time I took my mini-rebellious habit of strolling around upstairs naked down to the first floor. I had to smile at myself as I headed back upstairs. I was happy with how the evening went and while it went further than I had initially expected I was glad I did what I did.

Returning to my room I slipped into some undies and an old tee shirt and remembered the texts I had gotten from the girls. Putting that on hold for a minute I figured I first owe Jon a text saying that I got home ok and that I had a good time.

Me: Jon thanks for a great night, it was better than I had expected, based on the movie you suggested.

I added the last bit just in case someone saw the text. About 5 min later I heard the familiar ping alerting me to a message.

Jon: Great I am so glad you enjoyed it. I am looking forward to the next time we can get together so that we can watch the sequel. Night

Me: Me too, Night

Turing my attention to the girls I group texted them.

Me: Hello fellow adventurers!

Ana: Hey sooooooo.......

Me: I was thinking I might drag this out a bit to get a rise out of you too, but I don't have the heart. It went great, Jon was a perfect gentleman, well in the sense that he followed the rules and didn't try to push the process beyond where I was happy. ????

Elle: So, what did you guys do?

Me: You know the rules, exactly what we did will stay between Jon and me. ???? I will only say that I have added a couple more "firsts" to my resume and leave it at that.

Ana: Understand. Just one question, do you want to continue?

Me: Absolutely

Ana: That tells me everything I need to know. LOL

Me: Night ladies

Ana: Love you guys

Ella: Talk tomorrow.

I guess that Jon and I broke the damn so to speak in that after we had confirmed to the others that it went well (I assume that Jon and talked with Andy based on his comments in the group chat), because it seemed that invitations started going out a couple times a week for the Posse members to "Hang Out" almost immediately.

I know that both Ana and Ella were able to connect with Andy over the next week or so. As with my hang out with Jon I only got the barest details from both of them. But they both did confirm that Andy too followed the rules exactly as they had agreed.

I managed to connect back up with Jon the following week for a short Hang Out. And true to his word he did return the favor, and quite well I might add. From my side I basically did the same thing to him this time that I did with the second time we did it last week. Although there was probably a bit more mouth and a bit less hand this time.

I did think about pushing my boundaries a bit more but given the small window of time I decided that would wait as I did not want to feel rushed when I did.

As luck would have it, my parents decided at the last minute that they would go visit my sister over the weekend and would be away Saturday evening. I was excited that I would be able to host my first a 'hang out'. Hopefully there was at least one willing co-conspirator

As I was crafting my note, I was aware that for this part at least I wasn't in charge. Once I sent the note out it would be up to fate if it was Andy or Jon would be coming to visit. I decided that I did like that bit of uncertainty.

Me: My parents are heading out of town this weekend to visit my sister and will be gone Saturday night. Anyone interested in hanging out Saturday night?

After I hit send, I was surprised how anxious I felt awaiting a reply to my text. A couple minutes went by and a text from Jon appeared, stating that he had to work late Saturday and tried to swap with someone else but there were no takers. 20 minutes later I heard from Andy, he had been driving at the time, and he replied that he was free and would enjoy hanging out.

Continuing the conversation directly with Andy.

Me: I was starting to get worried that no one would be available on Saturday, and I would miss my first chance to be the instigator of a hang out session.

Andy: Yes, I bet sorry about that. I have promised my folks that I won't text while driving and I try to abide by that promise.

Me: Saturday 8 work for you? How long can you stay?

Andy: 8 is perfect, if I get home around 10-10:30 that would not be viewed as unusual by M&D.

Andy: So, what do you have in mind?

Me: If it is ok with you, I think I would like to max out at oral?

Andy: That is fine with me. Do you need me to bring anything?

ME: A smile? ????

Andy: See you then.

As I thought about sending the invite I had pretty much decided that if it was Jon who responded first I would have suggested we have sex. But since it ended up being Andy, I decided that I was not comfortable enough with him yet to take that big a first step. So, I decided to stick to blowjobs for now with Andy. Even so I knew there were still a couple of available firsts possible that evening.

OK now that the timing and activity were set, I wanted to come up with a plan to kick it off since this was our first time. Thinking back to the first time with Jon and the whole towel scene I was thinking that while that was accidental (Hmmm or was it, I need to ask him next time we are together whether that was really an accident as he indicated.) something similar might be an interesting way to get us started.

By the time Saturday evening rolled around I had decided to take the direct approach. He had already seen me naked at Ana's party, and there was no secret why he was here. Around 7 that night I went upstairs, took a shower, put clean sheets on my bed and straightened up my room a bit.

When the doorbell chimed just after 8, I headed downstairs naked. Positioning myself behind the door and out of sight of any of the neighbors I went ahead and let Andy in. Once he was in and the door closed, I did a little pirouette for him, grabbed his hand and led him up to my room.

Once in my room I plopped down on the bed on my side with my head supported on my hand and asked, "So how did you like my greeting." "While it was not what I was expecting, it certainly wasn't unappreciated." He replied with a smile. "Since this was our first meet up, I wanted it to be memorable." "I would say you succeeded splendidly." He retorted. Which put a big smile on my face.

"Do you have a preference for how we get started?" I asked. "Well since you are naked let's start with you, if you have no objections." He shared. Taking his queue, I rolled over on my back spread my legs the width of the bed and looked at him. Taking the hint, admittedly it was a bit more than a hint, he kicked off his shoes and socks and climbed up on the bed and positioned himself between my legs.

As this was our first time I took his hand in mine, and I did the same 2-3 minute tour of my body that I had done with Jon our first time. At which point I lay back, closed my eyes and let him do his thing. 20 minutes or so later I had sufficiently recovered from an excellent release. I sat up and suggested that we trade places.

Faster than I almost thought was possible he was naked and lying on the bed and I was between his legs. I started much like a did with Jon by starting to slowly stroke him. As I picked up my pace, I could feel him starting to get harder. Figuring now was a good time to switch tactics; I lowered my head and took him into my mouth.

Andy's smaller size allowed me to take more of it into my mouth without gaging, and it also was a lot more comfortable for me. I briefly thought about trying to see if I could deep throat him, but I quickly decided that I would have to wait for another time. The one thing that was different in what I did with Jon was that I did not ask Andy to warn me before he erupted. I decided that I would check that first off, my list tonight. I wasn't sure I would swallow it all, but I would let him cum in my mouth.

15 minutes later I had successfully added that first to my done list. I was a bit surprised by the first blast I had him pretty far in my mouth when it happened and that blast basically shot straight down my throat, which caused me to gag slightly which resulted in me repositioning my mouth before the second blast so that just the head was covered by it allowing the rest to accumulate in my mouth. I did swallow some of it, but I must admit that I let most of it ooze out of my mouth as I slowly sat up as his softening erection fell from my mouth.

At this point I got up and headed to the bathroom to allow me to get cleaned up and to bring back a warm washcloth to clean up Andy. Returning to the room I climbed back between Andy's legs and used the washcloth to clean him up. Somewhat surprisingly I noticed as I was finishing up that he was starting to get hard again. I looked up at him and he just smiled and shrugged his shoulders.

I glanced briefly at the clock on my bedside table and asked Andy, "What time do you need to leave?" With a bit of a mischievous smile he replied, "I have time." With that I jumped up and headed to the bathroom to drop the washcloth in the sink. By the time I got back to the bedroom I was again sporting a very impressive erection.

Deciding to have a bit of fun with him I said, "Any thought on what we should do about that thing sticking up between your legs?" As I nodded at his now full-on erection. "A couple." was all he said. "Care to share them with me?" "So as to keep within the original boundaries we set but to still expand our experience how about we try and 69 to see if we can manage to cum at the same time." "Deal." was all I replied.

Andy positioned himself flat on his back with a pillow under his head. I slowly climbed up onto the bed and carefully positioned myself over top of Andy and lowered myself down onto his chest. After a couple of minor adjustments to our relative positions we seemed to settle into a complimentary rhythm. I must admit that while it was not as stimulating, at least to me, as when it was just me being satisfied. Mentally it was an awesome turn on. I was wishing I could be a fly on the wall to witness it.

We were not quite able to accomplish the goal of cumming together, it seemed that one or the other of us would lose focus on what they were doing as they approached their orgasm. Once we realized that Andy offered to finish me first and I returned the favor shortly after. Afterwards I rolled off him and swung around and laid down next to him.

"Well, that adds 2 new 'firsts' to my list, thank you." I said with a smile. "I assume the 69 was one of them, what was the other one?" He responded. "You are correct on the 69, but I will let you guess on the other one." I responded with a wink. "Fair enough." was all he said in reply.

Glancing at the clock he stated that he had better start to think about heading home, adding that it might be fun for the two of us to jump in the shower together. I told him he needed to get himself cleaned up this time, as I didn't think my jaw muscles could manage a third time with a chuckle. He jumped up and headed into the bathroom.

10 Minutes later, after a quick rinse in the shower he was back in my room getting dressed. While he was dressing, I did thank him for a fun evening and shared that I looked forward to knocking out a few more 'firsts' with him. Which prompted a, "It was my pleasure, and I am more than happy to help you knock out a couple more 'firsts'. Reply from him.

Pulling a robe from my closet I walked him down to the front door and gave him a brief hug and I let him out. Walking back upstairs I realized that I wasn't kidding about my sore jaw as I rubbed the sides of my face. I slipped off the robe and climbed into bed naked (taking full advantage of my parents being out of town). I picked up my phone and quickly scrolled through my messages, seeing nothing urgent, I put it down, turned off the light and I was quickly asleep.

The next week or so was mostly quiet on the posse front. I think the initial newness of the whole plan sparked a rush to try stuff which I think we all enjoyed. But there was some amount of a return to the mean after that initial wave. We all had summer jobs, other friends, and commitments, and if for no other reason than to keep up appearances we all wanted to keep meeting as a group as we had since the 4th grade. After all it might be our last summer together.

The following week we had an interesting scenario come up that we hadn't thought about. On Tuesday Ella sent out a "Wanna hang out?" text to the group and immediately got a positive response from both Jon and Andy within seconds of each other.

About a minute later both Ana and I got a text from Ella asking what she should do. Ana replied, "Well there are really only a couple of options. The rules, such that they are, state that the first person to respond has the right of first refusal, which would be Jon based on the time stamps of the texts. But clearly you could pick Andy if that is who you really wanted. After all it is your body. But I am pretty sure that would not be received well by Jon."

Much to my surprise and I assume Ana's Ella responded with, "Yes that was how I was thinking about it as well. Would it be all right if I asked them both if they would be willing to all meet together?" After a pause Ana replied, "If it is ok with the 3 of you then I don't see why not." At which point Ella responded with a smile, "OK let me think about it.".

I quickly texted Ana.

Me: Do you think she would really do a threesome?

Ana: I don't know I assume you were as surprised as I was that she even mentioned it.

Me: Yeah, no shit!

Ana: Maybe we will get some indication of what she chooses to do as the week goes on.

As it turned out there wasn't another mention of the Friday hang out by Ella, Andy or Jon for the rest of the week.

The curious was killing me so Saturday around noon I texted Ella.

Me: Ella, so how did last night go? ????

Ella: It was fun.

Me: Ok, I get it, following the rules. Can I get a hint?

Ella: Hmmm, ok let me just say that I am pretty sore this morning in some sensitive areas,

Me: WOW!! Ok that is cool. Respect!!

After the initial shock of that discussion that whole topic was eventually forgotten. While I really wasn't sure if I would be brave enough to do it if she was happy she did it, I was happy for her. It did however prompt me to decide that I need to knock off the last major 'first' and finally have full on sex with one of the guys. My chance came a couple days later when John sent out a 'hang out' text for the following Saturday. Which I immediately replied yes to.

John: Does 8 work for you?

Me: Yes, I get off work at 7 so that gives me a chance to grab a quick shower and have some dinner.

John: Great, what are you comfortable with for the boundaries this time?

Me: I have thought about it a lot and I think I am ready to go all the way with you if you agree.

John: If you are sure, it is a big step, but I am all in if you are.

Me: Yes, I am sure.

We texted back and forth on a couple of housekeeping issues, when I had to be back home, the fact that I have been on the pill for several years to help control my periods, so no need to worry about any condoms, was there anything in particular I wanted to try, etc. Once we got all that sorted out, I returned to helping mom prep dinner.

I was surprised that I wasn't more nervous as the week went along which told me that I was in fact ready to do this. When Saturday rolled around, I finished work, headed home for a quick shower, some leftovers for dinner and I headed over to Andy's house.

Walking over I was curious if Andy would respond in kind and answer the door naked as I did with him the last time, we were together. It turned out that he was slightly less creative than I was, but he did put some thought into it. After ringing his doorbell, I got my answer. After the door opened, I saw Andy standing there in just a pair of boxers. He caught me glancing down at his boxers and commented as if he was reading my mind. "I thought about it, but we have a partially see-through front door, so.....". Which caused me to chuckle.

After closing the door, he looked at me and repeated his comment from the other day. "Seriously if at any time you start to feel uncomfortable just let me know." "OK." I replied. He then said, "Are you ready to head upstairs?" Looking him straight in the eyes I said, "Take the boxers off!" Which I think caught him a bit off guard. After a brief hesitation he slipped his thumbs in the waist band and quickly dropped them to the floor and kicked them off.

Grabbing his hand I quickly led him up to his room. I had been in his house a 100 times or more and even in his bedroom a couple times when we were working on school projects and such. So, I knew the way.

I watched in fascination as I led him to his room how his erection went from about a 45-degree angle to almost 90 degrees in the short time it took us to get upstairs. Reaching his room, I led him to his bed and gently pushed him back down onto it. After coaching him into the right position, I climbed up on the bed and got between his spread legs.

Grasping his now fully erect penis on my right hand and gently cupping his balls in my left hand I began to slowly start to stroke him. This elicited an immediate soft moan from Andy. As I slowly began to pick up the pace of the stroking, I began to gently massage his balls. After another 5 minutes of this I could tell he was getting close based on the amount of precum that was leaking out as well as he almost incoherent moans.

Deciding now was the perfect time to change tactics, and I slowly lower my head down and took the head of his penis in my mouth and began to slide it up and down in rhythm with my hand. After a couple of minutes of this he tapped my arm, and I looked up at him. He then asked, "Would you mind taking off your top for me?" My first thought was what is it with guys you have a pretty girl between your legs getting you off and your first thought is man I need to see her tits!! Boys!!

Realizing I would get there soon enough anyway I went ahead and sat up. Deciding to take full advantage of the situation I reached down and grabbed the bottom of the hoodie I was wearing and very slowly started pulling it up. The whole time I am watching his eyes get bigger and bigger the higher the hoodie went. After finally pulling it off his eyes Immediately dropped down to my bra covered breasts. Slowly reaching behind my back I unhook it and hold it in place for a minute at which point his eyes are basically pleading with me to take it off. Deciding to put him out of his misery I slipped my bra off and fling it across the room.

I then placed my hands on my breasts and begin to sensually play with my nipples. One trick I learned one day when I was home alone was that I could just barely suck on my right nipple, figuring this was as good a time as any to show that to him. I lowered my head and did just that. This put me in a position to stare directly at his penis, which I could see was actually throbbing as I was sucking on my nipple.

I was only capable of doing that for a couple minutes before my neck started to cramp. Figuring I had teased him enough, I dropped the nipple from my mouth and lowered my head back down and took him back in my mouth. I knew he was close to cumming, so I wasn't surprised when he erupted most immediately after I resumed the blowjob. Like the last time I got him off with my mouth I let him cum in my mouth but at the same time I let it ooze out around his softening penis.

After he finished, I sat back on my heals and asked him how I did? His only response was, "Amazing." Sliding off the bed I made my way to Andy's bathroom and got myself cleaned up. Returning to Andy's bedroom with a damp wash cloth as I approached the bed, I flipped him the washcloth and said as I started to unbutton my jeans, "Get up it's my turn now." Which prompted him to clamor off the bed while finishing his clean up.

By the time he returned from the bathroom after deposing the washcloth there I was naked lying on his bed in almost the exact same position he was a couple minutes ago, It was clear when I slipped off my undies that I was very wet at this point. As he climbed between my legs and lowered his head down to start to go down on me, I said. "You don't need to get me off this time. Can you just do it until you are ready to go again?" I couldn't wait to see what it feels like to finally have sex.

After 5 years or so of inserting tampons, not to mention various experiments I did with hairbrush handles, carrots and a few other household items I wasn't really that concerned that it would hurt but I did know that this was going to be the biggest thing to breach my outer lips. But as horny and wet as I was as well as the smaller dimensions of Andy, I wasn't worried. After about 10 minutes Andy stopped and looked up at me and said he was ready. Which for a minute pissed me off since I was very close to cumming. Remembering that I had asked him to do just that I said, "OK."

As he started to reposition himself, I said, "Wait, can you lie on your back and let me be on top? I would like to be able to control how fast we go." He didn't really respond but he rolled off me and onto his back. At which point I straddled him, I reached down and gently took a hold of his penis and put it in the right position and I slowly started to lower myself down. After a minute or so and a couple of minor position changes I had completely lowered myself on to him. I rested there for a bit as walls of my pussy grew accustomed to the size of him. My first thought was 'WOW' the fullness feels amazing.

I then started to slowly raise and lower myself off him, only an inch or so at first but as I grew more comfortable, I started to increase both the frequency and the amplitude of the motion. After a couple more minutes of this I knew I was ready. Rolling off him I said. "Andy I am ready let's see what your got." Which brought out a laugh from both him and me. Swapping positions on the bed he crawled between my legs and with a little help from my hand he was again fully encased in me.

He then began to move himself in and out of me slowly at first but quickening his pace as time went on. After about 5 minutes it hit me like a ton of bricks my first orgasm from 'real sex' and it was awesome. The best part was that Andy slowed down a bit to let me recover but as soon as I had he again quickened his pace, and I was very quickly almost ready to cum again. I asked him to slow down a bit as I want this to last a little longer and to be able to enjoy all the sensations.

Slowing down to about half the speed he was going I just lay there and enjoyed all the feeling I was experiencing. While I clearly liked the part of him that was sliding in and out of me, I also like the feeling of him laying on top of me, the feel of his breath on my neck, and how my nipples felt as the slid across his chest as he moved.

Several minutes later he whispered in my ear that he was getting close and wanted to speed back up if that was ok. I quickly nodded and he resumed his earlier pace. All too soon I again reached the point of no return and with an almost animalistic scream rockets again went off in my head and I shuttered, my pussy clenching and releasing his penis. Seconds after I came, I felt Andy speed up just a bit more and I could feel him literally erupting inside of me as his penis spasmed.

After was both calmed down, he carefully rolled off me and we ended up side by side on the bed, both of us breathing heavily. After a brief respite he turns his head toward me and asks, "So how was it?" Somewhat sheepishly I quickly replied, "I want to do it again!" Which caused us both to crack up. After laying there for almost 10 minutes I glanced at the clock and with a sigh shared, "I guess the replay will have to wait. I better get cleaned up, dressed and headed back home."

Andy handed me a couple of tissues, I could already start to feel him oozing out of me. Taking the tissues, I cupped my hand between my legs, slid out of the bed and headed to the bathroom. 10 minutes later I was back in Andy's room, mostly cleaned up but still oozing a bit. But I was very satisfied with how the evening went, sharing exactly that thought with Andy. Rummaging around his room for a bit, I eventually recovered all my clothes and got dressed. I gave Andy a quick hug and started to head downstairs, with Andy close behind me. Looking back at him I said he didn't need to show me out. As we got to the bottom of the stairs he reached down and picked up his boxers that we had left there. Smiling he said, "I know, but it would be a bit hard to explain to mom and dad why there were here." Smiling I watched as he put them on, I turned and opened the door and walked out and headed home.

The only thing I can remember about the walk is that I am sure I was grinning all the way home. And that I was glad that the first time was with someone I knew and admired and that it wasn't hurried. Mission accomplished!!

The following Tuesday we all got a text from Ella announcing that her parents and brothers were once again headed out of town for the weekend for another soccer tournament. And as she put it, she was again offering up her pool for a skinny-dipping redux, if we are interested. Given how far we had come in the past year I was pretty sure I knew what everybody's response would be and that I was sure there would be no backing out this year. Sure enough, within 5 minutes everybody had confirmed they we in. After a brief round of, what time, what should we bring and the like we had the details set, 7 PM Saturday at Ella's house.

After dinner I headed up to my room and grabbed my suit to keep up appearances in front of the folks and a towel. I headed back downstairs and said goodbye to mom and dad, and I was off. Entering Ella's backyard, I saw that she and Jon were already in the pool, and as I walked up to say hi, it was clear that there would not be a repeat of last year's timidness as both were clearly naked.

With a chuckle I turned around and out of habit started to head toward the cabana they had adjacent to the pool where, historically, we had always gone to change. Catching myself after step or two I turned and dropped my suit, towel, & purse on an empty chaise. I quickly stripped off what I had on and dove in.

The first thing I noticed was how different it felt as my naked body moved through the water. My first thought was that I was pretty sure I could get used to that feeling. Surfacing right between Ella & Jon we began chatting awaiting the others. Andy and Ana arrived together and quickly stripped off and joined us in the pool. As they too surfaced it again struck me on how far we had come in the last year.

Shortly after everybody arrived it was suggested by someone that we organize a chicken fight. We had done this many times before, however none while naked, so this would be interesting. In the past given his size advantage, Andy and whoever was on his shoulders, usually ended up being the winner. But we didn't care, it was always a lot of fun, and we usually ended up exhausted and sore from laughing so hard.

After several rounds of fights with all the girls getting a chance to be on both the guys' shoulders at least twice we called it a game. As predicted, Andy won most of the games, but Jon did a good job making a fight out of it. I did notice that there was a lot less concern about what you were grabbing than how we played in the past. Working to recover from the work out we all just casually floated around the pool We had known each other for years and now that we had all been having sex with each other over the summer the setting was very relaxed.

At one point I was sitting on the edge of the pool with my feet in the water when Jon came over and we started talking. Subconsciously, I noticed after the fact, I spread my knees apart and let Jon stand between them as we talked. Something we had done many times in the past. As I glanced down, I realized that I clearly had no secrets from Jon now and smiled to myself.

15 or 20 minutes later I noticed that Ana and Andy had disappeared from the pool. I assumed that they had decided that they wanted to do more than just look so I kept my eyes open to see if I could spot them. Sure enough a short time later I spotted them both leaving the cabana. When Ana caught me looking at her, she just shrugged her shoulders in a, it is what it is, kind of way, and with a mischievous grin on her face she proceeded to lick her lips. Glancing over at Andy I also noticed that he seemed a bit deflated as well. Thus, confirming want Ana had hinted it.

I thought about seeing if Jon was interested in something similar, but I realized that it was starting to get late and as if on queue Jon mentioned that he needed to be heading home as he had to be at work early the next day. We all agree that as sad as it was it was time for the evening to come to an end. We all soon exited the pool and began drying off and getting dressed, I was still somewhat amazed how quickly this all had become normal. To cover all my bases, once dressed I dipped my suit in the pool to get it wet and then wrung it out and wrapped it up in my towel. Making a note to myself to leave it that way on the dryer when I got home.

The next couple weeks were uneventful, there we a couple of 'hang outs' arranged but none by me, although not by a lack of interest on my part. My parents seemed to be determined to spend as much time with me as they could this final summer before college.

My next opportunity came when my folks announced that they were headed to my mom's old college roommate's daughter wedding the following Saturday and they we planning on staying over Saturday night and driving home the next day. After I confirmed the details with Mom, I sent out a note to the posse. Jon was quick to confirm his availability. I assume he was just as interested in having sex with me as I was with him.

Me: Jon thanks for accepting, I'm looking forward to it.

Jon: Me Too ????

Me: From my side I am good to go, no limits if that works for you.

Jon: Yes, fine with me.

Me: See you Saturday at 8.

Jon: K

In the end the Saturday visit went just as well as, and roughly through the same steps as my last 'hang out' with Andy did. He was somewhat thicker than Andy was, so it took a bit more time for me to get stretched out than it did with Andy. But once we had it was just as pleasurable. We also tried a couple of new positions that I hadn't tried with Andy. Working with a limited data set the one I seemed to enjoy most with Jon was the doggy style. Not sure why but I came twice while we were in that position. When it was over I was just as happy with the experience as I had been with Andy.

I was able to connect with Jon and Andy each one more time before summer ended. And while I was never in a position to try the supposed 3-way that Ella did. I did manage to meet up with Andy and Jon on successive nights. That probably deserves a check in the 'firsts I box I would think. Even with a 24-hour break between them when I awoke on Sunday, I was pretty sore. I guess I am not quite ready for two in one night. Yet????

The week before a couple of us headed off to school I got a text from Ana.

Ana: Hey, are you busy?

Me: No, not really, what's up?

Ana: I would like to ask you for a really big favor.

Me: Sure, what do you need?

Ana: OK here goes, would you like to 'hang out' with me on Saturday night?

Me: (After pause) You mean like hang out, hang out, like we have been doing with the guys this summer?

Ana: Yes but let me explain further. I have been thinking about this for couple weeks and I finally got the nerve up to ask you before our summer break ended.

Me: OK

Ana: Don't take this the wrong way but I am really not trying to hit on you, but like we did with the boys I would really like to experience sex with a girl before I head off to college. Please don't share this with the others but I think I might be Bi.

Me: First off, while I certainly won't share it I really don't think the others would care one way or another. Just sayin. Secondly, I feel honored that you felt comfortable enough with me that you could share this. I know it was probably hard to do. Can I think about it overnight?

Ana: Sure! And if the answer is no I get it, no hard feelings I promise.

Me: Ok, I will text you tomorrow. See ya.

Ana: You too, and thanks for taking this seriously.

Ok well, that came out of nowhere. As with most difficult decisions I have faced I decided to let it roll around in my head for a bit. At least in my experience not rushing to an answer has worked out pretty well for me over time. Instead, I headed downstairs to grab some lunch.

After lunch I headed back upstairs to start packing for school. Between the information that the school sent on what to bring and my sisters own experience I had a pretty good idea of what I needed and for the most part Mom and I had already done most of the shopping we needed to do to complete the list.

After about an hour of sorting stuff into different boxes I took a break. Thinking back at my recent text exchange with Ana, I decided that I did not want to leave her hanging on my answer overnight. It clearly took a lot of courage to ask so the least I could do was give her a quick answer.

Me: Ana, can you talk? (I figured it was better to not leave a text trail of this discussion.)

Ana: Give me 10 min and I will call you, ok?

Me: Yes, and lest you are freaking out I think we can make something work.

Ana: ????

A short time later my phone rang, it was Ana.

Me: "Hello Ana, what's up?" I figured I would tease her a bit initially.

Ana: "Ha-ha. Before we get too deep into the conversation, I wanted to make sure you knew how much a appreciate your willingness to help. And just to be clear just like with the guys I want us both to be on the same page if we decide to do something."

Me: "I know Ana. First, I need to say that while I was initially surprised by your suggestion in the end, I decided that it was 100% in keeping with the whole concept for the summer between the 5 of us. I also need to share that to be honest this is not something I would have reached out to you to try. That being said, I am willing to give it a shot with the one caveat that if I get too uncomfortable, we abandon the effort, OK?"

Ana: "Of course I am totally aligned with you on that. Here is my suggestion, remember back in middle school when we used to have sleep overs, and we used to take turns giving each out a back rub?

Me: "Yes of course"

Ana: "Let's start there and see what happens. Maybe all we get out of it is a good back massage which isn't a bad place to end up either,

Me: "I think that is a great way to start. OK I'm in, let's do it. It will be our final sleep over before we venture off into the brave new world of college."

We spent a couple more minutes coordinating the final details and said our goodbyes.

Walking up to her door on Saturday evening I was a bit nervous but not as bad as I thought I would be. After a quick knock Ana answered the door like she had the 100 other times I had knocked on her door. We spent the next hour just really talking about how excited we were to be starting college and how much we would miss each other. We did 'borrow' some wine from her parents to relax us a bit since neither of us were planning on leaving the house.

Around 10 PM Ana suggested that we head up to her room. Knowing what this could mean I thought I would have been more nervous but the time we spent hanging out, along with, I am sure, the two glasses of wine I had seemed to quell those nerves. Once upstairs we each made a quick trip to the bathroom and met up in Ana's bedroom, dressed for bed (T-shirts and undies).

Once there she offered to start by giving me the first massage. As I was climbing onto the bed, she suggested that I take off my T-shirt which I was happy to do. As I positioned myself face down on the bed she climbed on top of me and lowered herself down so that she was straddling my hips as she sat. She leaned over and reached into the drawer of her nightstand and pulled out a bottle of massage oil.

Sitting back down on my hips she opened the top and poured a small amount on the middle of my back and some on her hands. Then she began to work the oil into my back slowly starting with my neck and shoulders. At which point two things struck me. First was that she was very good at giving massages. I made a mental note to ask her later how she got so good at it. Her hands seemed to have the perfect balance of strength and softness. Secondly, I realized how much I needed this massage. As she stared to release more and more tension from my body it almost seemed like I was sinking deeper and deeper into the mattress.

I am not sure when it happened but the next thing, I knew the sun was peeking through the curtains in Ana's bedroom and I was under the covers, in just my undies with Ana spooning me from behind, her right arm draped around me. As I stared to stir, I felt Ana begin to wake up as well. "Good morning sleepy head." She whispered in my ear. As I became more aware of what was happening it dawned on me that I fell asleep in the middle of the massage totally ruining Ana's evening plans.

Turning around to face her I immediately began to offer my apologies for falling asleep on her. I asked her why she didn't wake me up I knew that this was important to her, and I felt really bad about screwing up her evening. Placing her finger over my lips she looked me in the eyes and shushed me. Talking in a quiet measured tone she assured me that it was all right. She did think about waking me up but the more she thought about it this was something she wanted not something that I wanted to do, so she let it go. She continued that she had learned a lot about herself and her sexuality this summer that she was sure she could figure this part out when the time came.

I replied, looking at the clock, that it was still early we could do some fooling around now. I assured her that I would be happy to take part. Smiling mischievously back at me she said, "Cary we are good. You have no idea how happy it makes me that you were more than willing to jump in with both feet, well maybe only one but close enough. Plus, while you were sleeping, I copped a couple feels of your various body parts." At which point she broke out laughing and reached over and tweaked one of my nipples.

Realizing the moment passed I rolled back over and pulled her arm back around me and we lay there for another 30 min or so. At which point Ana said, "Well I need to use the bathroom, and I am getting hungry." And climbed out of bed and headed to the bathroom, returning a couple minutes later.

As she walked back into the bedroom I figured I had better do the same and I too crawled out of bed. As I got up to head to the bathroom, I reached down to pick up my T-shirt. Which prompted this comment from Ana, "You can leave that off if you like." Looking at me like a cat that ate the canary. "I would but I think it would be cruel of me to parade around topless in front of you with this almost perfect set of tits!" Was my retort. At which point she lunged at me and grabbed me from behind and immediately grabbed both of my breasts and began to massage them. "Ha I would say more like average than almost perfect;" At which point we both broke out laughing and eventually collapsed into a heap on the floor. Eventually we were able to untangle ourselves at which point Ana got up and helped me up, and with one final look at my 'almost perfect tits' she flipped me my T-shirt and I put it on. After a quick trip to the bathroom, we headed downstairs and tracked down some breakfast.

An hour or so later fully dressed I was standing at her door when she came up to me and put her arms around me and gave me a big hug. As she did so she whispered in my ear, "If you ever change your mind about the whole girl-girl thing let me know. Oh, and despite what I said earlier I too think your tits are almost perfect." At which point she gave me a somewhat chaste kiss on the lips and ended the hug. Smiling, I turned around and walked out the door headed home.

Later that week we all got a rather cryptic text from Ana.

Ana: Meet at the clubhouse at 7pm Friday if at all possible.

Despite some initial conflicts outlined in subsequent text we all made it there as requested.

After some initial small talk between us Ana stood up and cleared her throat. "First, I want to thank you all for making the effort to me here. I felt it was important that we ended the summer somewhat like we started it with a group meeting. This one is a bit more bittersweet than the one at the beginning of the summer though and probably leads to less sex." Which got a chuckle from the rest of us.

"Jon and Andy leave this weekend for college and the rest of us leave over the next week. So, as your unofficial leader, I wanted to share with all of you how important you have been in my life. I have known you all for almost 10 years and you have both watched and helped me grow into the person I am today. Thank you all very much!"

At which point she paused and let us all add our own thanks to the group. Leave it to Jon to add a final irrelevant comment, "And thank you all for a great summer of sex!" Which cracked us all up. "And with that I would like to move to adjourn the final meeting of the Vine Valley Verve!" added Ana.

--- FIN---

As always constructive comments are always appreciated. I am sure that some will feel it necessary to point out my editing failures, unfortunately that seems to come with the territory. More helpful would be comments on style, plot, story ideas and the like.

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