Boy Story: The Road Taken - 44. The Best Summer Ever

The Best Summer Ever

As spring changed to summer, so had our relationship changed when I began living with Parker. During the school year, we only had short bursts of time together before I’d have to go back to campus. In addition, we were restricted to getting together just a day or two a week, so it was important to get as much as we could out of those few times together. Fooling around in a theater, car, museum, amusement park, or wherever became commonplace. We were forced to multitask because the hours we were together seemed to fly by like minutes.

Summer changed all of that. We didn’t have school to contend with, and I didn’t have to run back to campus. Suddenly we had lots of time together, and sex wasn’t relegated to quickies whenever (or wherever) we could squeeze it in. Now sex could last for hours…OK, tens of minutes. And even if we got off quick, it didn’t matter because we had plenty of time to rest, reload, and repeat.

In past years when I was living at home with my parents, my summers were a mixed bag of family, friends, and alone time. This year, summer was going to be very different, but I would still have to make time to visit my family once a month. Also during those visits, I’d make plans to go out with my hometown friends. Of course, this would all take place in the absence of Parker. However, this free time would give him the chance to get together with his friends: Connor, Jenny, Barbara, whoever. Since I was with Parker all of the time when I wasn’t working, these little weekends apart were probably a good way of keeping our individual friends from feeling ignored. One thing for sure, I could not divulge my relationship to my friends and family, so I had to keep silent about my life with Parker. I was the product of a very conservative community, and that came with a price. My family and friends didn’t have much of an opinion regarding same sex relationships, and any opinion they did have would not have been complimentary. So, unless attitudes suddenly changed, the less they knew, the better.

Aside from visiting my family, the summer was shaping up to be a lot of fun. I got into a routine of working, cleaning the pool, and taking Parker on trips to keep him (and me) entertained. I’d never had a companion 24/7 when not working, so this was a bit of a change for me. Some people like to have a little alone time, and I did get it at work when I was out tending the greens. But I often found myself daydreaming and looking forward to the end of the day when I would be home again with Parker. He was forever on my mind.

When I returned home from work, I’d skim the pool daily, clean the filter, check the chemical levels, and once a week I’d vacuum the pool. Parker would usually assist me with pool duty, however, he would never remember to tend the pool on his own. I guess he just needed some incentive, and I was happy to oblige.

Their pool was interesting. It was above ground and oval with a redwood deck surrounding all sides. There was a set of stairs that lowered much like those pull down stairs you’d see for attics. The stairs led to a deck area on the near end that could accommodate a couple of lounge chairs and a table and chair set with umbrella. The rest of the deck area was just wide enough to comfortably walk around the pool. There were also these green fiberglass privacy panels surrounding the sides of the entire pool deck with a height mid way between my belly button and sternum when I stood next to it. So the whole pool area was enclosed inside a sort of green fiberglass corral.

Additionally, Parker’s house sat on a cul de sac, so the houses and yards on either side did not line up in a grid. This meant that the houses next door didn’t look out on your back yard or in your windows. The neighboring properties were angled away. Plus, there were bushes and evergreen trees that were planted in between the properties providing a bit of a privacy screen.

Since most of those summer days were warm and sunny, we’d wear just a pair of shorts (no need for underwear) when tending the pool. Daily skimming took all of 15 minutes. Then when I announced it was done, Parker would drop his shorts and jump in. I would happily follow.

We never saw any reason not to skinny dip while in the pool. And of course, if you put two nude boys who have the hots for each other in a private, enclosed pool area, you’re going to have a little more than swimming going on. Our favorite activity was to lie nude in the two-man inflatable raft and just cuddle and float. Eventually one of us would give in to temptation and the whole thing would devolve into an exhibition of overactive hormones. Since the pool was the simplest way to beat the heat, our usual afternoon sexual activities moved out of the house and into the pool for the summer.

Once his clothes were off, Parker was happy to remain naked in the absence of anyone else at home. I really enjoyed watching when he’d walk from the pool to the house to get some snacks for us. The image of his cock bouncing up and down when he walked to the house is burned into my brain for all eternity. I’d always seen him nude in bed or standing or even sitting, but there was something alluring about him walking around completely oblivious while all of his boy bits were bobbing all over. I guess it was the newness of it, seeing him in a state of motion that I rarely had the opportunity to witness. I could watch that all day long and never tire of it.

The only times we’d wear a swimsuit in the pool was when Ginny was home. Although we generally knew her work schedule, we still kept our swimsuits by the pool in case she came home unexpectedly or we had the schedule wrong. We always had plenty of warning because she had one of those car alarms that beeped loudly to let you know the car was locked. Since she generally worked day shifts, it usually wasn’t an issue because she got home at a time when we were done with the pool for the day.

Ginny didn’t use the pool that often, however, there were a few windows on the second floor of the house that faced the back yard. Two of Parker’s bedroom windows and one of Ginny’s bedroom windows looked out on the pool. There was also the bathroom window, but it was frosted and opened like a vent preventing any view of the yard. Needless to say, our skinny-dipping and canoodling were curtailed when Ginny was around. Otherwise, our activities in the pool were nude and frequently X rated.

To prevent the chance of being surprised by visitors, we’d lock the stairs leading up to the pool deck preventing unexpected guests from gaining access. Therefore, we had plenty of notice to make ourselves presentable if there was ever any need to. We were surprised only once when Jenny and her friend Trish showed up because Parker had made plans with them, but he had forgotten what day it was. We quickly slid our suits back on before lowering the stairs to the pool deck.

Aside from pool endeavors, we did manage to accomplish much when I was not working. I frequently took Parker down to the high school to practice driving in the parking lot. It seemed to me that neither Parker nor Ginny were in much of a rush to get the boy a driver’s license, so I made it my mission. When he felt ready, we scheduled a driving test when his mom would be free and they could use her car. Not surprisingly, he passed on his first try and finally at age 18, he had his very first driver’s license.

In other news, we did make it to the Museum of Fine Arts. I remember the sheer amount of art in the museum was staggering, and attempting to cover it in one day was a daunting task. The paintings by Monet, Donatello, Rembrandt, Van Gogh, Singer-Sargent, Norman Rockwell, and Grandma Moses were just scratching the surface. There were wood carvings and Egyptian art and sculptures from artists whose names were lost to antiquity. This place was much larger than the Gardner Museum we had gone to before.

While on our route, we came to a sparsely populated area in the museum. Parker told me to “Wait here. I’ll be right back.” He turned and went back into the room we had just come out of. Then a few seconds later, I heard a very loud fart come from that room. The sound emitted bounced off the flat walls creating a kind of reverberation. He walked back into the room with a completely innocent expression and looked at me.

“Was that you?” he asked.

“No, but I know what that noise was and who made it,” I replied. “It was pretty loud.”

“Now they’ll have to change the name to the Museum of Fine Farts,” he whispered and we both started cracking up.

“Well, let’s keep on going this way. That room back there kinda smells,” he said and we both started laughing again.

Our day at the museum ended with a walk through the gift shop. They had a lot of really interesting, overpriced toys and gadgets and educational devices. There was a glass jewelry counter and I was thinking, “Who would buy jewelry in the gift shop of a museum?” There was also a little display of rings and a sizer. “Hey, check it out. Do you know what your ring size is?” I asked him.

“No, do you know yours?”

“Nope, but I’m about to find out. Let’s see…no…no…close…ah, I guess that makes me an 11,” I said playing with the sizing rings.

“Like your cock,” he whispered.

“Ha ha, you wish!”

“I certainly do!”

“You wouldn’t know what to do with 11 inches,” I teased.

“I seem to know what I’m doing with 9 inches, so what’s two more?” he retorted.

“It’s not 9 inches,” I reminded him.

“Here, let’s use the sizer to find out,” he joked.

“This sizer is not for that! Here measure your finger before I give you a time out.”

“Hmph,” he muttered as he ran his fingers in the rings. “There, see it’s 9 1/2, even bigger than I thought,” he said with a testy grin.

“Don’t start up with that again!” I mock warned him.

“Hey, I have to whiz. Where’s the restroom?”

“Way down at the end of that hall,” I said pointing in the direction.

“Care to join me?” he asked. “I’ll let you aim it.”

“No, I think that would just lead to trouble.”

“OK, fine, then I'll meet you back here,” he said as he walked toward the restroom.

I went back in the gift shop and made a purchase, which we'll hear about later. When Parker returned, we decided we had enough culture for the day and decided it was time to leave.

Aside from our excursions and routines, there were the “wild card” days. Sometimes when I came home from work, we didn’t end up in the pool until later. He’d sometimes set up an ambush for me when I got home, and it was usually quite…unique.

He wanted to tie me up on the bed once. We found the ropes to be a hindrance to the sex. I guess you’re supposed to tie up someone who doesn’t want to be molested, so bondage didn’t really work. Another time he was sitting nude in the living room waiting for me. He told me to “shut up.” He began giving me orders. “Oh I get it, this is a master/servant role play thing,” I quickly realized. Well, it was either that or Parker had suddenly lost his mind.

He told me to call him “sir,” made me do a striptease in the center of the room while he played with himself, and then he ordered me to get down on my knees and blow him. It didn’t take long for him to relieve his burden in my mouth. It seemed like years since he’d said that it was “an acquired taste,” but he was right. I found myself anxiously anticipating his boy milk. I don’t know if all cum tastes the same, but I did “acquire” a taste for Parker as time passed. I didn’t mind worshipping him because, in my eyes, he was perfection, and who doesn’t want the opportunity to commune with perfection?

But one ambush stood out above all others when it comes to mind as the most extreme. I was never really sure what the goal was, but I don’t think it went as expected. It was the time we went out for ice cream.

I returned home from work on a Friday, Parker met me at the door, we made out for a while, and he led me by the hand to his bedroom. “I have something special to show you,” he said excitedly. We got to his room and he unwrapped an object that was completely foreign to me.

“What is it?” I asked.

“Isn’t it obvious? It’s a butt plug,” he announced.

“A what?”

“A butt plug.”

“For what?”

“For your butt, silly,” he said matter of factly.

“Huh?”

“You’ve never heard of a butt plug before?”

“Uh, no.”

“Well, you lube up this end and stick it up your butt,” Parker elaborated.

“And why would I want to do this?” I inquired.

“It stretches out your butthole to help with your future bottoming experiences. Plus, it feels really good. And it’s a bit of a turn on because if you’re wearing clothes, no one knows it’s there.”

“Where?”

“Aren’t you listening? Up your butt.”

“Parker, do you see the size of that thing? It certainly won’t fit up my butt.”

“It’s only a medium.”

“A medium! Christ, it looks like a fire hydrant.”

“Ha, ha. It’s shaped that way so it stays in place,” he explained.

“It will never fit. It’s just too big.”

“It will fit. I’ll prove it to you,” Parker declared.

From day one, bottoming was never a painful affair for me, but maybe a little stretching would help ease the minor discomfort. I went to take my shower with Parker and his new toy. We showered together and then he asked, “Is your butthole fairly clean?”

“I did douche last night before bed,” I informed him.

“That should do. Ready to try the butt plug?”

“I don’t know, Parker. Why don’t you try it.”

“I have my own butt plug. I bought this one specifically for you.”

“It’s too big though!” I maintained.

“Oh c’mon, it’s smaller than mine for god’s sake.”

“I find that hard to believe,” I stated.

“Don’t be a baby. Just try it, and if it hurts, we can stop.”

“All right.”

“Look, we can do it right here in the shower,” he suggested.

“But do what?”

“Just bend over while I lube this thing up. And then I can lube up your hole a bit.”

I stood there bent over while he slid lubed fingers up into my hole. I was wavering between feeling violated and feeling stimulated.

“Now, I’ll go nice and slow, OK?”

“You’d better!”

“Geez, I thought you were brave.”

“Bravery doesn’t usually entail getting big things shoved up your ass!”

“Shush. Now spread your legs a little more to get your butthole to open,” he directed. I changed my stance while he stuck two fingers up my hole. Once they were all the way in, he moved the fingers all around while I groaned.

“Ready? Here we go.”

I felt something stiff against my hole and then it slowly slid in. It felt a lot like getting fucked.

I felt some resistance. “See, I told you it was too big. Aargh! Tell me when it’s half way in, OK?” I complained.

After about a half minute, “There!”

“It’s half way?” I asked. He stood out in front of me and showed me his hands were empty.

“Wha—?”

“It’s all in!” he said.

“No way!”

I quickly reached around to my butthole and the only thing sticking out of my ass was the base. I was thinking this is crazy. I could go through my entire life without ever knowing about the existence of butt plugs and be perfectly content. But I guess that was no longer an option. I had a large butt plug in me...yeah, I know, Parker said medium size. I guess they must run big.

“Turn around. Let me see,” Parker squealed. “Now bend over. Oh yeah, that’s hot,” he said assessing his handiwork while caressing my ass cheeks. Parker gave a little tug on the base ensuring it was firmly locked into place. Then he grabbed a towel and dried me from my shower.

“Now what?” I asked.

“Get dressed.”

“Get dressed?”

“Yeah, get dressed. We’re going out. You’re going to buy me an ice cream,” Parker decided.

“I am?”

“Yup.”

“Aren’t you forgetting something?”

“What’s that?”

“There’s a butt plug up my ass. Remember?”

“I’m not forgetting. The ice cream is for me. The butt plug experience out in public is for you,” Parker explained.

“Parker, how will I know what to do?”

“You don’t have to do anything. The butt plug will stay in place until you yank it out. No one will know it’s there except for me and you…our little secret.”

“And how are we supposed to get there?”

“We’ll drive of course.”

“And how am I supposed to sit down and drive with this thing up my ass?”

“Sit down just like you normally do. It’s made for that. Or I can drive if you want.”

I began to weigh the options. Do I let newly-licensed Parker drive my car there or do I attempt to drive with a fire hydrant up my ass?

“Here,” I said handing my keys to Parker. “But pay attention and don’t wreck my car!”

“Woo hoo, I get to drive!” Parker cheered.

As I sat in the passenger seat and Parker drove us to the local DQ, my full body weight was down on that butt plug. I felt my insides getting a little more penetration than I imagined possible. I felt my butthole throbbing as we neared our destination. I just wanted to get out of the car and stand again so I’d take some of the pressure off. Why did I let Parker talk me into this?

“Here you go, I’ll park over here so you don’t get your doors bumped,” he said as he parked toward the back of the building.

This DQ was a stand-alone building that many people would call a hut, and it was only open May through October. It had a paved parking lot around all sides and a small area on one side with wooden picnic tables for customers to sit and eat. It was a short walk from the high school, so it was a popular stopover for teens walking home or on their way to the shops downtown.

“So did I drive OK?” he asked.

“Yes, it was like Driving Miss Daisy,” I joked.

“Hmm, don’t tempt me,” he replied.

We checked out the menu posted in the side window for a few minutes to assess our options.

“Well son, what’ll you have?” I asked him with a chuckle.

“OK, Dad, I’ll have the usual,” he said.

Now he didn’t expect that I knew what “the usual” was because he usually ordered his own, but he enjoyed teasing me a little bit. I suddenly felt bad that I didn’t know what he wanted. I felt that I should know everything about him, especially what ice cream treat he fancied.

“And what exactly is that?” I inquired.

“A hot fudge sundae, with vanilla ice cream, whipped cream, and nuts. You know how much I love nuts,” he said with a smirk.

“Yes, I am very aware of your fondness for nuts,” I assured him.

There was only an older guy with probably his granddaughter ordering at the window. We would be next. That’s about when I heard, “Parker! Parker!” from behind us.

“Hey, Lori…and Jenna! Oh my god, it’s great to see you,” Parker called out as he turned around.

A conversation then commenced that I couldn’t follow because I was called up to order at the window. To make things easy, I decided to get the same thing as Parker, and I put our order in. From what I could follow, he knew the two girls from school, from the swim team, and they were a year younger…soon to be starting their Senior year.

When I approached with the sundaes, Parker saw that there was no one else in line, so he motioned the girls to the window and invited them to join us at the picnic benches once they had their ice cream. It suddenly occurred to me that sitting on a wooden bench with a butt plug inside me was not going to be pleasant. But it didn’t matter because we were going to be sitting there regardless. I sat down gingerly but still let out a groan.

“You OK there Matty boy?” Parker joked.

“I’m just reminding myself that this is your fault,” I replied.

“You’ll thank me later,” he said.

“I doubt it.”

The girls approached with a cone each and sat with us.

“Parker, is this your brother?” Jenna said looking at me.

“No, this is Matt…my boyfriend,” he said confidently.

“Oh, really? I didn’t know you were gay,” she said surprised. I saw a hint of disappointment in their eyes. There was a sudden realization that Parker would not soon be dating either one of them. This led me to believe he was very popular with girls in general. And then I figured it was foolish to think otherwise. He was beautiful.

“In fact, Matt is going to be my dorm mate in college in the Fall. Isn’t that right, Matt?” he said trying a tactic to drag me into the conversation.

“Yes, it makes everything really convenient,” I responded.

“So Matt, you’re gay too?” Lori asked. Normally this would be considered a question from a girl who obviously had no full grasp on what being gay was all about, but it kind of worked when it was applied to Parker and me.

“Nah, Matt’s straight, but he lets me molest him from time to time, ha ha!” Parker joked.

Trying to keep the conversation clean, I added, “Parker can be very convincing. So I gave him a shot and the rest is history.”

“So are you still straight?” Lori followed up. I looked at Parker as if to say “Is this girl for real?”

“Yup, my boyfriend is straight,” Parker said stating his favorite motto.

And in unison, both girls said, “Oh.” This was getting weird. I just wanted to get out of this interaction without Parker informing them that I was well endowed and had a butt plug up my ass.

There was a little more chatter about people they knew and some experiences from the previous years, and then it was thankfully time to go. Of course, Parker offered them a ride home and they accepted. I didn’t say anything because I figured it was the right thing to do even if Parker was behind the wheel...and I had a butt plug up my ass. We pulled up at Jenna’s house and Parker got out with them. They hugged Parker and everyone wished everyone else good luck next year. They said it was nice meeting me and I said likewise.

As we drove away, I said, “Gee Parker, you’re a big hit with the girls.”

“Yeah, I guess. Imagine if I was straight,” he posited.

“Ha ha. If you were straight, you’d be a father by now!” I declared.

“Ah, but if men could have babies, I’d be a mother by now!” he joked.

“And if you were straight, I wouldn’t be sitting here with a butt plug up my ass!” That did it. We both cracked up laughing. “Oh god, don’t make me laugh, it’s hurting my butt,” I exclaimed.

“Hey, it was your joke!” Parker reminded me.

We pulled up to the house and, as was usual for this time of day, Ginny’s car was not there. As we walked up to the house, Parker said, “Well, thanks for the ice cream, Matt!”

“You’re welcome, son,” I replied.

“Son? I thought you said that I’d be a father by now.”

“Yeah, but I’ll always be older than you.”

“Yes, you're my daddy with the big dick!” he added.

Well, it was only a matter of time for the dick reference to emerge. Thankfully, it wasn’t in front of two unsuspecting girls.

We went straight to the bathroom because I really needed to get that plug out. Since this had the potential to get a little messy, we ran the shower and got in.

“Now bend over. I’ll pull and you push, OK?” Parker instructed. At first I was sure it was stuck, but as Parker pulled harder, it began to move and then slid right out, along with a farting sound and a good amount of lube. Parker washed the plug (which I hoped to never see again) and I washed my ass area. I was relieved it was out, but now my butt region felt a little odd.

“Turn around, let me see,” Parker directed. “Whoa, look at that. You’re gaping!”

“I’m what?”

“You’re gaping. Your hole is staying open. That’s what’s supposed to happen when you remove a butt plug. Oh look, that’s so hot!”

Well, there was no way for me to get a good look at anything that was completely behind me. I could have tried a double mirror set up or something, but that would have been too much work. This was obviously why it felt different. My butthole didn’t close.

“I want to fuck that hole right now,” Parker disclosed.

Oh so maybe that’s what this was all about. He wanted to feel what it was like to fuck someone, namely me, while that person was gaping. I wasn’t sure what to think at that moment. I was all for experimentation, but my butt had already received quite a workout.

Well, I figured I enjoy getting fucked and I’ve gone through this whole ordeal with the butt plug, so I might as well follow it through. I got on the bed on all fours so he could do me doggie style. I was not quite prepared for what came next. Since my butthole was open, Parker was able to pull his rod out completely and shove it all the way back in again without using his hands. It made a sucking in and sucking out sound with each thrust. The feeling was one of ultimate penetration, and I had a white knuckle grip on the bedding as a result. At first I was kind of enjoying the new sensation, then it started to feel sore.

“Look Parker, I don’t mind trying something new, but the way things are feeling back there right now, I don’t think I can go much longer.”

“OK, I’m almost done,” he groaned. So I held out long enough for him to finish. He grunted several times while shoving it way up into me and, after a few seconds, his body went limp. He was done.

At this point I wasn’t feeling particularly horny, but I had a hard-on that I needed to get rid of. I turned onto my back and began jerking off. Parker took my lead and moved in with his mouth until I gave up my liquid reward. We then both went to the bathroom to clean up.

"That was a really hot fuck! Thank you for holding out until I finished."

"Well, I'm just used to finishing things I've started," I informed him.

"And now you'll be used to finishing things I've started," he declared with a mischievous grin.

Returning to the bed after a full day’s worth of events, I felt Parker nudge up against me and I nodded off in no time.

“Hey, Matt!” waking me up was the next thing I remember.

“Yeah, what’s up?” I said trying to regain consciousness.

“Are you hungry?” Parker asked.

“Yeah, a little bit, sure,” I said trying to assess the situation. “Why?”

“Well, it’s like 8:00…”

“In the morning?”

“No, it’s Friday night at 8:00. I’m ready for dinner. You want me to make you something?”

“Nah, why don’t you order some delivery…Chinese food or something.” I reached over and grabbed my wallet off of the nightstand. “Here’s $40…and $5 for the tip…knock yourself out. Just nothing spicy, OK?” I put my head down and fell right back to sleep.

Parker’s mom kept a kitchen drawer full of restaurant menus from places that delivered. So Parker knew the routine and left the bedroom to place the food order. I’m not a picky eater, so any type of ethnic or non-ethnic food was good by me. He knew what I liked.

“Hey,” I heard a voice urging me back to consciousness.

“Huh? Oh…did you order the food yet?” I asked.

“The food is here!” Parker announced.

“Already?”

“Whaddya mean? It’s almost 9:00!” Parker exclaimed.

“Oh shit, really? I guess I was really out of it,” I said evaluating the situation. “Here…help me up,” I said reaching my hand out. He grabbed onto my wrist and pulled me up until I was vertical again.

“Ha ha. Wow, dude you’re so naked!” he said looking at me.

I suddenly felt underdressed. “Of course I’m naked. I was just in bed,” I tried.

“I’m not complaining. I’m enjoying the view!” he confessed.

“Oh man, my ass is sore. And my hole feels like it’s still open,” I replied as I took a step.

“Really? Let me see.” I turned toward him, bent over, and he checked things out. “Oh yeah, it’s still gaping a little…but not as much,” he reported.

“Yes, it’s very sore…like inside…and outside,” I added.

“Gee, Matt, you really have to be more careful in the future,” he teased.

“I think that’s going to be nearly impossible with you around.”

“Are you suggesting that I’m a bad influence?”

“I’m suggesting that from now on nothing goes up my butt except smaller-sized, well-lubed body parts.”

“How about fresh fruit?”

“No.”

“How about…”

“No.”

“Aw, you’re no fun.”

“Really? This is no fun?” I asked as I grabbed my cock at the base and waved it around a bit.

“OK, I stand corrected,” Parker declared.

The soreness subsided in a day or two, but during that whole time my butthole was kind of propped open a bit. I was somewhat nervous that it would stay that way forever…that I had done some kind of irreversible damage. Without the ability of my butthole to close all the way, I had a fear that I wouldn’t be able to keep my shit in. But eventually my fears were allayed when it did close and things went back to normal, save for some temporary itching from inside. It was uncomfortable for a couple of days and then it too disappeared.

From that point forward, this one experience gave me the power to say “no” when it came to trying sexual things that seemed unreasonable. It’s like burning your hand on a hot stove, and then having the presence of mind never to do that again.

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