Rob's Summer Adventures
Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 04 Dec 2017
Rob’s Summer Adventures – Part 5
The following weekend was a visit from Billy. As it was just Billy, the boys slept in Rob’s bed which meant they had to be quiet so as not to disturb Dad. In low tones Rob told Billy all that had gone on in his visits to Jay’s.
You have to find a way for me to join you, Billy insisted, not for the first time.
I’ll find a time to ask, Rob promised.
I really don’t know what he’d think. That issue
settled as much as it could be, they turned their attention to a favorite pastime – getting
each other off. It was late, so they didn’t make any effort to prolong things, but certainly were satisfied
The weekend continued much the same. Dad took them for an outing on Saturday, finishing up with dinner out. When Billy’s parents came to get him and visit with Dad on Sunday, Rob promised that he would talk to Jay.
Monday morning Jay chatted briefly with Rob, comparing their weekends. Jay had been out of town with some of his other friends, but didn’t let on what they did. Rob said Billy had visited and left it at that. Tuesday he had a better opportunity to bring up the subject of Billy visiting Jay. Jay invited Rob to lunch. They picked up sandwiches and found a quiet bench where they could chat and enjoy an outdoor lunch.
After a few minutes Rob started telling Jay a bit more about Billy. Jay knew about the roommate,
but not much more.
You were open with me about Barry, so I guess I owe you the same. Without the
truly intimate details Rob told about how he and Billy liked to play together and often shared the bed.
He left out Hank and Sam and any of the others. There might be time for that later. Jay was happy for
Rob that Billy was able to visit sometimes during the summer. Rob saw that as his chance.
So, I was wondering. . . Could. . . Well, could Billy meet you sometime when he’s here?
Just meet me? Or get his clothes off at my apartment? Rob could tell from Jay’s
tone that he wasn’t offended by the question.
We’ll just have to see how things develop. Rob accepted
that answer and they returned to work.
That afternoon Jay got started on a plan of his own. From Rob’s employment papers he had contact
numbers for Rob’s dad and took the liberty of calling him at work, assuring him that there was no cause
for concern. He apologized for taking up Dad’s time at work and was told that it was fine.
use a break, Dad told him.
Wasting no time Jay got right to the purpose of his call. His family had a house in the country,
about a two hour drive away. He would like to have Rob join him this weekend. Dad gave it a moment’s thought,
then gave his ok, telling Jay that he felt Rob was in good hands, and that he was eighteen, after all,
so could make his own decisions. Dad might have said no if he hadn’t felt good about Jay. He did thank
Jay for taking the time to consult him, which only helped to raise Jay in Dad’s estimation. Jay was surprisingly
effusive in his thanks which brought another
not to worry from Dad.
At 5:00 Jay stopped by Rob’s desk and quietly asked if he would stay for a few minutes. Rob was perplexed, but Jay showed no signs of annoyance or disapproval so Rob decided it must be something other than a talking to. After the office was fairly empty Jay told Rob of his plan and that Dad had given permission for Rob to join him. Rob was thrilled! He also felt a sense of pride that Jay would want his company for a whole weekend. As much as he enjoyed his project at work, Rob felt the rest of the week went by at a snail’s pace. Thursday night he packed an overnight bag, put his toiletries in it Friday morning, and took it to work with him.
After what felt like an endless day 5:00 arrived. Jay came over and said
ready kiddo? Rob
was, and eager, too. For some reason he hoped that others wouldn’t see them leaving with Rob so obviously
prepared for an overnight. No one did. About halfway to the house Jay stopped at a favorite diner which
had better than the usual diner food. He told Rob it would be about another hour’s drive. Also to order
whatever he wanted.
Jay’s family had a caretaker who looked after the house. He also was helpful with various other things, so it was no problem for him to have the house stocked with all the food they would need for the weekend, saving Jay a trip to the grocery store.
It was getting dark when they arrived, but Rob was able to get a good look at the house which was very much what one would expect of a second home in the country. It also was isolated from any other houses which secretly pleased Rob. It took only one trip to unload the car. They went in through the kitchen where they took off their shoes.
Now came Rob’s first surprise. Before he could pick up his bag Jay said, in firmer tones than Rob
had heard him use before,
Rob, take off your clothes. Rob expected he’d have naked time over the
weekend, but this felt like an order. He started to remove his shirt.
You will be naked here all weekend unless I say you can put on clothes, which would be only if
someone comes by. I’ll probably spend much of the time naked, too, but you will be naked full time. You
will understand what this is about as the weekend goes on.
By now Rob was out of his clothes, a bit stiff with nervousness. Jay told him to gather up his bag and his clothes and follow him. Jay said he’d show Rob the house but first they should get their things put away. Jay led him to a comfy bedroom also furnished with a king-size bed like Jay’s in the city. He showed Rob where to put his stuff then, to Rob’s surprise, went about settling his things in the same room. Rob wasn’t sure what to say, so said nothing, but he guessed that he would share the bed with Jay. This was exciting! For the moment Jay stayed dressed while he took Rob around the house.
In the living room Jay explained some things to Rob.
You and Billy, and I’m guessing some other
friends, have been having a lot of fun playing together. This is good, but playtime isn’t only what sex
is about. This weekend I hope I can help show you that there is a different kind of pleasure, much as
my mentor did for me. There will be other things, too. I hope you will learn a lot over the next couple
of days and that it will be good for you.
Rob didn’t follow what all of this was about except that he could tell that Jay was showing a special
interest in him. He nodded. With a smile Jay stood up and undressed. That done he took the familiar spot
on the couch that he had used at home two weeks ago and invited Rob to nestle up against him. Rob was
only too happy to do so. Jay’s arms around him made Rob feel comfortable. Jay was silently showing Rob
affection without causing Rob the usual teenage sexual need. They stayed that way for quite a while. A
bit after 11:00 Jay said
let’s get to bed. He took Rob by the hand and led him upstairs. At any
other time Rob would have felt he was being treated like a child by holding hands, but this only added
to the warm feeling that was enveloping him tonight.
That night Rob had his first lesson in real lovemaking. Jay was gentle, patient, and genuinely glad to share this with Rob. Rob let Jay lead. What few words they shared were either a question or a bit of guidance from Jay. Jay brought him to an orgasm unlike any he’d had before.
During all this Rob felt Jay’s erection for the first time. When he had the opportunity he took time
to explore how it felt, with Jay’s responses gratifying him. Before it became more serious Jay took Rob’s
hand off, wrapped him in another hug, and said
It’s ok. That can wait until morning. You need to sleep.
Rob sighed and fell asleep almost immediately. Jay happily held the sleeping boy and drifted off to sleep.
They woke up at the same time, both hard. It was time for Rob to learn about making his partner happy. Again, quietly and patiently Jay guided him. As he came to better understand how it felt to be providing pleasure rather than just the biological urge he had with his friends, Rob adjusted his style, trying to be more aware of Jay’s needs and pleasure. When it was over Jay complimented on Rob on how he’d done. Rob was a quick and eager learner.
Before they went down for breakfast Jay unveiled another thing to come.
You will get a spanking
today. It’s time you find out what a spanking is. Rob’s face went white, but something inside told
him that Jay was right. Hearing Jay’s words also confirmed to Rob that indeed he did want to be spanked,
especially by an older man. His stiffening in reaction was all the proof needed. Jay noticed and knew
he’d made the right decision – a decision he had intended to make, regardless of how Rob felt
Rob recovered and they went down to breakfast. Jay did not say when the spanking would happen or what would happen during the day before the spanking. As he intended it to, this lack of information did play on Rob’s mind. Jay said nothing more and otherwise treated the day as a normal one. It was not his goal to torture Rob with anticipation, but it was good for Rob to wonder a bit.
Jay continued to show Rob nothing but affection throughout the morning. While still aware that at some point he was to be spanked, Rob relaxed and enjoyed the attention. Jay made it clear that Rob was to help with lunch, which he gladly did. He was eager to please this man who was showing him such care. He knew, without being told, that his eagerness to please would not mitigate the spanking to come.
Through lunch Jay was no different. After eating, Rob was assigned to do the cleanup, putting leftovers away, filling the dishwasher, and cleaning up the kitchen. Jay needed to do some other things for a while and left Rob to his task. That done, Rob wandered into the living room. He found a magazine which looked interesting, curled up in an easy chair, and soon was engrossed in an article. He didn’t hear Jay come in.
It was Jay’s voice which caught his attention.
Good, you’re already in here. It’s time, son. Rob knew what it was time for, reinforced by
Jay calling him
son. His nervousness had him hard, but there was nothing to be done for it. Jay,
now dressed, sat in the middle of the couch. He explained to Rob how he was to lie over Jay’s lap, then
helped him into position. Jay rested a hand on Rob’s bottom and explained what was about to happen.
There are different kinds of spankings. What you will get now is what is often called a maintenance
spanking. That means that it is not for punishment but as a reminder of what misbehavior will get you.
Barry gets true discipline spankings. The occasional maintenance when he and I feel he needs it. Perhaps
one day you will get a true discipline spanking, perhaps I won’t ever have you in this position again.
In some ways that is up to you, though I may decide someday that another maintenance will do you good.
Do you understand?
Yes, sir, Rob said. Having been called
son he felt that
sir was appropriate.
Jay showed no reaction.
Yes, sir, Rob answered, the trepidation clear in his voice. Jay proceeded to give him a classic
maintenance spanking, not too hard but enough to give Rob’s bottom a good sting and some warmth. This
was nothing like a spanking from Fred. Fred was cocky and felt he was superior. He used spankings as a
way to prove it and get an upper hand over his friends. Maybe it was different with Ted, but any time
Rob had been spanked by Fred it was a power game. This was different. Even getting spanked Rob knew that
this was done with affection; that Jay cared about Rob and a spanking was not just so that Jay
could assert his position but rather that Jay knew Rob would benefit from the guidance a spanking can
provide when necessary.
The spanking was not particularly long and featured some rest moments. Jay knew how to get to a steady rhythm, bringing sting and some color and heat to Rob’s bottom. This was harder than the one at the apartment but did not hurt all that much. Yet, Rob found it was bringing on a desire to cry. Tears not of pain, but from the combination of the sting and the almost overwhelming feeling he got from the caring attention being given him.
As Rob’s eyes were truly tearing up he heard Jay saying
that’s it, son. You’ve taken it very well.
I’m proud of you. With a gentle rub to Rob’s bottom Jay told him to stand up. When Rob was standing
Jay indicated that Rob should sit on his lap. Rob didn’t question it and gladly settled on Jay’s lap,
put his arms around Jay’s neck and gave vent to his tears. At any other time he would have been embarrassed
and humiliated crying this way, but not now. Jay held him tight, saying soothing words. When Rob calmed
down Jay held him a while longer then told him to go upstairs and get into bed. Rob didn’t know if this
was part of the routine, but did as told. As Jay expected Rob fell into a deep sleep, only waking up in
time for dinner, which Jay had waiting. When Rob came down Jay was naked again. He gave Rob a hug and
a kiss; Rob let himself savor it.
When dinner was over and dishes done, they went into the living room. Jay sat on one side of the couch and Rob nestled up against him. Now Jay asked Rob how he felt about the spanking. It was difficult for Rob to express his feelings, in part because he wasn’t entirely sure what they were. He said that in an odd way he was glad it had happened. He didn’t know if he wanted more spankings, but felt glad he’d had this one. Jay occasionally kissed the top of Rob’s head as Rob made his confession. Rob thought he might give way to tears again, this intimate time was feeling so good and almost overwhelming.
Discussion done they sat there a while longer, then Jay whispered that it was bedtime. Another night of lovemaking ensued with Rob learning more. His orgasm this night, after the spanking, seemed even more intense. This was a new world for him.
Over breakfast Jay assured Rob that he would not be spanked again. With a wink and a smile he added
at least not this weekend. Secretly each was thinking they’d like another spanking, but not this
time. Jay also was thinking that he would like the weekend to go longer.
Departure time would be around 3:00 Jay told Rob when breakfast was done. In the meantime Rob was free to do as he pleased. So far he had not really explored outside. It was plenty warm enough not to need clothes outside and there was no likelihood of anyone seeing him, even from the drive (should someone arrive). Rob spent the rest of the day exploring the property, including walking a ways into the woods.
He’d put on sneakers, but otherwise was still nude, enjoying the sensation of the sun and wind on his naked body. This was so different from those few times at camp. Those had been to have quick fun, this was enjoying being naked in nature. Rob laughed to himself because that seemed so corny, but he was loving it.
As lunchtime was drawing near Jay came out of the house, wearing only sneakers, too.
Like the property? He asked.
Yes! This place is great. You’re so lucky to have it.
I know. I wish I could spend more time here. Come with me, I want to show you something. Hand
in hand they went down a vague path, Jay leading Rob into the woods. After about a five minute walk they
emerged into a small clearing.
This is one of my favorite places. You’ll laugh, but when I was a kid and the whole family was
here, I’d escape out here so I could jerk off. The image of teenaged Jay naked in the woods stroking
himself got Rob hard. Jay was pleased by Rob’s reaction. Jay took Rob in hand and gently brought him to
an outdoor climax.
Now Rob returned the favor. He moved so that he could reach around and take Jay. He did his best to apply some of the techniques he’d learned this weekend. It seemed to work as Jay brought his older friend to an orgasm which the boy found quite exciting and hoped it could be repeated someday.
Well, we’d better shower again before lunch, Jay said after they had kissed some more. Back
at the house he showed Rob the outdoor shower. Standing under the spray they washed each other, then stood
in the sun for a while to dry off.
The expedition to the woods meant that lunch was later than normal. By the time they were done and had the dishwasher running it was about time to pack up to leave.
Jay, this was wonderful, Rob said.
Thank you for having me here. I would like to do it
again, if it’s ok with you.
Jay grabbed Rob and gave him a bear hug.
Of course it’s ok with me. I hope we can do this as much
as possible. Now, kiddo, go upstairs and get packed. And, unfortunately for both of us, get dressed.
Rob agreed that getting dressed wouldn’t be fun, but there was no choice. As he was finishing up his packing
and starting to dress Jay came up and did the same. He sent Rob out to the car while he closed up the
As always, Jay delivered Rob to his door. This time he got out to chat with Dad for a few minutes, complimenting Rob on being a good guest, one he’d like to have again. Dad was pleased to hear this. Did Dad wonder what happened that weekend? If he did he kept it to himself. He could tell that Jay was good for Rob which was what mattered.
Handshakes all around, Jay was off. After dinner Rob disappeared to his room to call Billy and relate
the whole weekend. Billy was agog listening.
That is SO hot! he said.
Damn, why can’t I find
someone like that? They both laughed.
Rob was surprised how tired he felt, so went to bed early. He woke up refreshed. Back in the office all was normal. No one there knew about the weekend visit and Jay betrayed nothing, nor did Rob.
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