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Rob's Summer Adventures
Part 9

by Brhmsj

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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: 25 Jan 2018

Rob’s Summer Adventures, Part 9

After that weekend that Rob and Billy shared with Jay in the country there were only two more weeks of work before the boys were off to college. They had applied to the same schools, been accepted at their first choices, made their decision, and were going to college together. Their request to share a room had been honored, too. They were getting excited about this new adventure soon to begin, but first Rob had to finish up his summer job. Billy couldn’t wait for his to end, he had found it boring, even with Jay’s admonitions about his attitude toward the job. Jay had made it clear that he would give Billy incentive to do his job well, should he deem it necessary. So far Billy had escaped that particular reason to get spanked though, as we know, with Billy there always were other reasons and he was well spanked for them.

The boys weren’t sure if they would be able to get together one more time before college. Jay said nothing about that, but did hope he would see Billy again. In the meantime, he wanted as much time with Rob as possible. Rob was hardly the first, nor would he be the last, teen that Jay mentored, but there was something different about Rob. He didn’t want Rob’s dad to wonder what was going on, but he also wanted Rob with him every night they could, not just the weekends. His chances were helped by Rob’s dad being away for a few days on business.

Rob and Jay had normal routines on Monday, but Tuesday morning Jay stopped Rob’s cubicle and quietly said that he hoped Rob could join him for dinner tonight. That was all it took to get Rob hard! Jay could tell what had happened in Rob’s pants. Rob no longer cared that Jay was seeing such reactions. He said he would be glad to have dinner with Jay. Rob also said that Dad was away tomorrow through Saturday. Jay said good, to both, and went about his business.

Mid-afternoon Rob called Dad at his office to say that he was having dinner with Jay that night. Dad chuckled lightly and said you are spending a lot of time with him. Rob, without realizing it, involuntarily gulped, just enough to be audible. Dad smiled. This confirmed what he had suspected almost from Rob’s first visit with Jay. He was pleased. He could tell that this friendship was good for his son and surmised that most likely they were having fun together sexually as it was continuing for so long. Little did Rob know that Dad’s business trip included staying with a long-time friend; staying not in the guestroom but in the man’s bed with all the activity that such an arrangement implied. Rob would come to learn about this aspect of Dad’s life eventually.

Rob was surprised that they did not go to Jay’s, but to one of the area’s best restaurants. It was discrete with all the tables situated such that conversation could be held easily, but not overheard by others. Rob, after a while, also noticed that the clientele were entirely men, many of whom were in pairs, as he was with Jay.

Dinner started with small talk, two friends chatting away. Jay noticed that Rob had caught on that only men were dining here. Quietly he said, as you’ve noticed, my friend, there are only men dining here. That is because this restaurant caters mainly to homosexual men. Or, as we prefer to say, gay men. From what I have observed, you have given little or no thought as to what to call your sexuality, but you certainly know that your interest is only in the same sex. I hope the term does not make you uncomfortable, but you are, Rob, a homosexual, a gay young man.

Rob spent a moment taking this in. He’d heard both terms. He knew that he and Billy, and Sam and Hank, had no interest in girls beyond casual friendships. Yet he and Billy had not ever thought of themselves in terms like gay, homosexual, or straight. They were what they were – buddies having fun together. Having it presented to him as Jay just did, however, made Rob think, and he knew Jay was correct.

So, Jay, I guess this means you are. . . you are gay, too, Rob said.

Definitely! And happily so, Jay answered, smiling at his young friend. I knew by the time I was twelve that I only was interested in boys. It wasn’t always easy to act on, but then in college I had more freedom, met some older gay guys, eventually Barry, and had some good times. As I told you, I also had a mentor who introduced me to what was special about man-man sex, lessons I’ve done my best to impart to you. Billy, too, I hope.

Sad to say, I’ve yet to find my true love, to use a cliché. Maybe I will, maybe I won’t. I don’t dwell on it, and I’m enjoying life. In compensation I get to spend time with young men like you. Rob blushed at this, much to Jay’s delight. Some I mentor, as it were, and send on their way. Some others have continued to be friends, and even playmates over time. No doubt this will embarrass you, but you have become very special. He was rewarded with another blush. It is a compliment, my dear boy. I think someday you will understand better.

That conversation done they turned their attention to ordering dinner. Rob had been hard throughout most of it, which was no surprise to him; he also knew that Jay was perfectly well aware that he was hard, but secretly enjoyed that Jay knew. Jay always found it special when a relationship with a youngster had reached this point, when he would know easily that the boy had gone hard from the topic at hand. Don’t worry, my boy, yours is by no means the only hardon in this restaurant right now. Again Rob blushed but also was thrilled to have this confirmation. It was something special they shared which showed their intimacy.

Dinner orders were given to a twenty-something waiter, handsome and buff. He let Jay know, by a look, that he was well aware that Rob was sporting a hardon under the table. Jay gave the waiter a small smile when Rob was busy with the menu. If the waiter remained discrete about this he would be rewarded with a healthy tip. As he turned away, Jay got a good look at the young man’s butt in tight black pants. Maybe someday a spanking would be the waiter’s tip. Jay knew the manager well and it was easy for him to meet the staff, should he want to. That would wait until Rob was off to college.

Appetizers quickly appeared and the waiter had fun standing close to Rob as he put the dishes down. Jay gave him an amused look of warning which was read properly, then they both smiled. Rob remained unaware of what was happening around him, though he certainly did notice the waiter and his firm buns. Rob also enjoyed the attention he was receiving, slowly catching on that it was because the waiter found him attractive. He said nothing to Jay, just let it happen and be flattered. Jay was having fun watching Rob’s growing awareness and responses. As the evening went on the waiter flirted with Rob who was unsure how to respond, but did his best. This was new and exciting!

Dinner arrived and now time was spent eating, with little conversation. The waiter took just a bit too long clearing plates, suggested the dessert menu, and discretely left when Jay said they would look and let the young man know when and if they were ready to order. The message was understood.

As they looked over the desserts, Jay spoke of the rest of the evening. After this we will go to my apartment. I won’t keep you out too late, don’t worry. Rob was thrilled. It was soon mitigated. We are behind on your maintenance spankings, son, and need to take care of that when we get to my place. Suddenly Rob wasn’t sure how much wanted dessert, but he also didn’t want Jay to see his discomfort. He didn’t know that Jay could read it easily, being so experienced with youngsters.

Do you really have to spank me tonight? Rob asked, with the nervousness showing in his voice.

Rob, you know this has been part of our agreement.

I know and, well... I do want you to spank me, Rob admitted. It just felt right to admit this to Jay. Jay smiled at him.

Very good, Rob. This shows you are progressing well. I’m proud of you. Rob blushed yet again – this was his night for that! I tell you what. To do it properly we really don’t have time tonight, so we’ll wait until tomorrow night when we have the time to do it right. Rob cheered up at that and happily turned his attention to the dessert menu. The waiter took their dessert orders. When he returned, without any pretense he touched Rob as he put down the plates. Rob enjoyed the attention and was rewarded with a warm smile from Jay.

Dinner done, they drove to Jay’s. Inside, Jay told Rob to take off his shoes. That done, Jay took the youngster in his arms. Hug finished he undressed Rob who felt a thrill at having someone so deliberately make him naked. Now nude, Rob received another hug, then instructions to go to the couch. Jay then undressed, took his usual spot, and held Rob. Nothing was said for at least an hour. Neither got hard. Time passed and Jay whispered, it’s time for you to go home. Tomorrow is a work day. Rob sighed, knowing Jay was right. They stood, hugged, and kissed, now both getting hard. We’ll have plenty of time tomorrow night. Since your dad is away, plan to sleep over. Now Rob was very excited.

When Rob got home Dad was still up – it wasn’t late. I have to leave early in the morning, so won’t see you. You know where everything is, so you’ll be fine. Let me know if you’re not coming home. Rob said yes, quite unsure why Dad would say that. They hugged, Rob holding Dad close, then up to bed. Rob was contented and quickly fell asleep.

The next day at work everything was normal, to all appearances. The few times Rob saw Jay he felt a thrill, knowing that that evening he would be naked over the older man’s lap, getting spanked. He hadn’t imagined he ever would want to be spanked, yet here he was, taken with this older man who cared for him; so taken that he wanted that man to spank him. And make love to him. He knew he’d get both tonight. Jay seemed to have a bit of twinkle when they did meet during the day. Right at five Jay was at Rob’s cubicle saying come along, young man. Rob had packed a small overnight bag, retrieved it, and off they went. For the first time that summer some of the other employees saw them leaving together, Rob with a bag over his shoulder. Most paid no attention. There were a couple who had an inkling; the one who had tried flirting with Jay at that lunch was envious. He never had an off-hours encounter with Jay, but Jay was quite aware of the young man’s interest. He saw to it that this young man met an older man when he got back to college. When he returned the next summer for a second year of summer work, he had been taken down a peg or two, as Jay intended. Yet, he never knew the whole story of that academic year, only that things apparently had gone as he hoped.

Back to our story. At the apartment Rob was sent to the master bedroom with instructions to put his things away and return naked. He also told Rob to bring the hairbrush that was on the dresser. Jay waited in the living room and was delighted to see Rob return, hairbrush in hand, sporting a full erection. He gave the boy a quick kiss, then took him to the couch. Better to do this on an empty stomach, he said as he took Rob over his lap. Jay guided Rob’s hardness between his legs and started in with a good, thorough hand maintenance spanking. For starters.

When Jay sat on the couch he had reached for the hairbrush, still in Rob’s hand, which Rob handed to him. Jay placed it on the cushion, positioned such that Rob would be able to see it while over Jay’s lap. Rob was more focused on what was happening to his bottom, but aware all the time of the hairbrush’s presence. He knew enough now about spankings that if the brush was there it would be used.

Hand spanking done, Jay paused and talked to Rob about the hairbrush. I rarely use a hairbrush for a spanking, though Barry gets it fairly often, as you might expect. Whenever I spend as much time with a lad as we have spent together, I feel it is appropriate for the lad to find out what the brush feels like. This is still maintenance. I hope I never have to use this for real discipline. Ready?

Rob quietly said yes, nervous and eager at the same time. He saw Jay reach and take the brush. Soon the brush was making contact. Rob jerked at the first one, then did his best to take this part of the spanking as he should. Ten, a pause, five more. Jay put the brush down and spent quite a while rubbing Rob’s bottom.

Spanking and butt rub done, Rob sat on Jay’s lap and once again gave way to tears, not of pain, but of overwhelming emotion. Jay comforted him, telling him what a good boy he was, letting him know he was proud of how well Rob had taken the brush.

Rob calm, Jay sent him to the corner while dinner was prepared, another first. Jay remained clothed through the meal. When he retrieved Rob for dinner the youngster was again as hard as he been earlier. Jay knew this meant fun for them both later. Another delicious meal. This time Jay told Rob he was to do all the cleanup. Jay watched as Rob did an excellent job, the kitchen in fine shape when he was done.

Very good, my boy, Jay said, as he undressed. Now, both naked, they went to the sofa where they took up the now-familiar positions. Rob had receded during dinner, but was hard again. He noticed that Jay was not, but felt so good in Jay’s arms that he didn’t care. Around eleven o’clock Jay led him into the bedroom. They went directly to bed; it was easily one o’clock when they were done. Jay took his time, bringing Rob near peak, backing off, then near peak again. By the time he brought Rob to climax the boy was as wild with erotic excitement as he ever had been. His orgasm was met not with a yell, but a series of whimpers, he was so overcome. Spent from his orgasm, he dissolved into tears again, this time tears of joyful emotion. Jay held him close. Without cleaning up they fell asleep, but only after Jay assured the young man that there would be time tomorrow night for Rob to do his part.

Jay had them up early. The hot tub was ready. Rob was put in it and the previous night’s dried semen was washed away by Jay. Rob happily let Jay wash him. Jay then quickly showered as Rob finished up. Before dressing they had breakfast and were back to the office. If anyone noticed them arriving together, nothing was said. Today Jay did show signs of excitement when he would see Rob, but nothing was said. Rob felt the same. He got his work done, but all day his mind was full of anticipation for the night to come.

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