Senior Trip

The next morning we had a full day ahead. We started the day with a short visit to a small museum, where they keep the David of Michelangelo. Then we started our tour of the city, with the Palazzo and the Ponte Vecchio, the graves of the Medici family and the Santa Croce church as highlights.

For me it was a great day. Figures, any history teacher would love this. I did notice Ryan, Joey, Kyle and Vince were trying to stay out of my sight. When our eyes did cross, they always almost immediately found something nearby or even on the ground to study with great care.

We got back to the hotel by 6 pm, so everyone had an hour to freshen up before dinner. I used that time as well to go the room of the four boys and tell them they were to stay behind in the hotel when the others were going out that night, so we could have a chat in private.

"Just tell the others you stayed up very late last night. Combined with the bus ride, that makes for two very short nights in a row, so people will believe you're too tired this evening. Besides, you probably won't be the only ones calling it an early night."

They clearly didn't like that idea, but it was the only way to avoid anyone else figuring out I was in the boys' room and getting disturbed while we were talking. So, as long as they didn't want anyone else to find out what they were up to the day before, the boys couldn't really find a way out.

Dinner went by rather uneventful, though I doubt I'd classify anything as 'eventful' when my mind was anticipating what was to come. As expected, there were some complaints about the food this time. The teachers were discussing the evening plans. I volunteered of course to stay behind with the students that weren't coming along, citing the very same reasons I had given the boys. A little over 9 pm the party people had left the building.

Joey actually did get a few strange looks when he announced he wanted to call it an early night. Some of his friends tried to convince him to come with them, but he stood his ground. It became easier for him as soon as his roommates 'decided' to stay in the hotel as well. After a few promises that they would be going out tomorrow with the rest of them, the others left the four boys in peace.

Meanwhile I was glad to see that there were only three girls of Turkish descent declining to go out as well. I knew them well enough to know they wouldn't cause any trouble. Probably they'd stay in their room and actually call it an early night. That meant my guess had worked out: no need for actual supervision, so I could spend all my time with the four boys.

"Ok, guys, why don't we go to your room, so we can talk in private."

When we got there, I made sure to close and lock the door. If everything would go to plan, soon there would be five naked people in here. I didn't need any interruptions then. I asked the boys to sit down on the beds, and chose a spot for myself next to Kyle. I made myself comfortable while making sure I could see everyone clearly.

"So, first of all, don't worry, I'd prefer this talk to end without any punishment for you. Second, I'm sure we all prefer to keep between us everything that is said in this room. Agree?"

The four of them were quick to nod their agreement.

"However, my silence doesn't come free."

This was enough to clear the obvious relief that had come in the room just a moment ago. It made way for a combination of puzzlement and touch of fear. So I decided to put them out of their misery and lay my cards on the table.

"I want you all to finish what you started yesterday. But, this time I want in."

"What? Are you gay?" Ryan protested.

"Why? You want me to suck your dick?" I snapped back. Of course, the whole reason for me to go here, was exactly that I wanted to see them naked again and watch all of them shoot their load. I felt that explicitly stating this particular desire though, might make them too self-conscious to come along with this. My retort was enough to shut Ryan up. Now I only had to redirect their line of thinking away from the being gay question.

"Look, guys, I noticed all of you were very uncomfortable today. Not towards each other, but when I was around. I think it's obvious that is because I caught you in an embarrassing situation, while you, between each other, were all equally involved. Now, I'll admit there's another reason why I want this. To make you understand this, I want to ask you first: what made you decide to go for a circle jerk to start with?"

Joey was getting a bit of a blush, the others were stammering a bit. I could almost hear them all thinking of which answer to that question wouldn't sound gay. And that's exactly where I needed them.

"Hard to come up with something that doesn't make you gay? Still, I'm sure you're all very much straight, aren't you?"

The way in which they agreed, was amusing to watch. Vince simply nodded, Joey was a bit slow to answer but after a second or two just said yes. Ryan almost nodded his head off, while Kyle as well went just a bit out of his way to make it clear he definitely wasn't gay.

"See? It's not really abnormal for straight teenagers to be doing something like this. It's hard to explain why you want to jerk off with some other guys, but trust me, you're not the first ones to go there. It's just the same for me. I've wanted to be in a circle jerk, but I never had the occasion when I had your age."

"Ok, I understand." The first sign that I was having success convincing them, came from Joey.

"You do?" Kyle clearly wasn't with the program yet.

"Well, yeah, besides, remember, we all want to keep this quiet, what happened yesterday ..."

That was easy for me. As long as Joey reminded them that my suggestion was what was needed to keep me silent, I didn't have to.

"Ok, I'm in." Vince was the second one to agree.

Ryan and Kyle looked at each other. They still weren't a fan of the idea. But after some thinking they reluctantly agreed as well.

As soon as everyone was in, Joey and Vince started to take off their t-shirts. Ryan and Kyle looked as if they were a little surprised by the speed things were starting.

"Guys, come on, you're not waiting for me to take of your clothes, are you?" I tried to push them on, while starting to unbutton my own shirt. It was enough to kick them into action. Soon enough all five of us were down to our underwear. We seemed to have arrived at another mental hurdle.

I suppose it won't come as a surprise to you that I already had a decent semi, that wouldn't take long anymore to develop into a full hard on. Judging by the strain on his boxers, Joey was getting there as well. From the looks of it, I doubted the other three were showing any physical signs of arousal yet. Besides that, none of them really wanted to be naked first. They were slightly stroking their dicks through their boxers, apparently hoping to postpone the inevitable. Some encouragement was definitely in order.

"So, Ryan, who do you think is the hottest girl in school?"

Ryan was a little startled, but on the other hand seemed thankful that he could now focus his mind on a girl instead of what was happening in the room.

"Euhm, I'd say Jenn."

Jenn was a senior as well. She had long, almost black hair and matching eyes, and a hint of a tan. Her figure was a typical boys' dream: slim with breasts that looked very large on her body.

"Tell us what you'd like to do with her."

"Euhm, I want to, euhm, get her naked and, euhm, I'd prefer to take her from behind. Her tits are hanging down, and euhm, while I fuck her I grab 'em so I can play with them. I can feel her hard nipples in my hands. She wants me to fuck her harder."

Ryan was clearly getting more into his fantasy. More importantly, all the boys were getting caught up in Ryan's little dream. Their boxers were starting to tent, and the light touches to their dicks were becoming a more full contact groping and stroking. But since no one was yet showing a willingness to actually take of his boxers, I decided to lead the way.

This was a little uncomfortable for just a moment. As soon as I got completely naked, I felt all eyes on me, looking at my dick that was now almost fully engorged to its six and a half inches. Ignoring the feeling of embarrassment, I took my dick in my hand and started jerking it slowly. At the same time I looked in the boys' eyes telling them without words I was waiting for them to follow my example.

Again, Joey was the first to move. He took down his boxers, and one reason why he was a little braver than the others became immediately clear. Joey was the only one that I hadn't seen in full glory the day before, but what I had seen already hinted at a magnificent package. The hints weren't deceiving: when Joey sat back up, an 8 inch dick pointing forwards came in sight, with a set of full loose hanging balls added to it. He had a nice patch of black pubes, though his sac was completely smooth. When he took hold of his dick and started to slowly stroke it, his well proportioned dickhead came in plain sight. All in all, Joey's cock was a true wonder of nature.

As much as I enjoyed the sight, I would have preferred Joey not being the first one of the boys to go fully naked. The others were a bit hesitant to follow his steps, and I couldn't blame them. As all members of the male species they were sensitive about their dicks, and almost any dick would pale coming after this one. It was obvious some encouragement would do them good.

"Come on, guys, I know no one of you wants to go next after Joey, but I think you all know there's absolutely no shame if you're not as big as he is. Maybe the best thing would be for the three of you to take the plunge together."

They seemed to come to an agreement by just looking at each other. It was even some unspoken sign that had them take of their boxers at the same time.

At the time I was most curious about Kyle's package, as he was the only one I hadn't seen yet. Kyle was of the twinkie kind, with wavy dirty blond hair. His pubes were almost matching in color. I estimated his dick at about 6 inches, crowned by dark red head. His low hanging balls actually did make his dick seem a little larger.

Ryan and Vince I had seen the day before, but it was nice to get the opportunity to study them more closely, though I still tried not to be too obvious about checking out their stuff. I suspected that especially Ryan might be rather self conscious about his size, and I didn't want to give him any reason to still back out.

I have to admit that I did have a preference for the larger dicks present, but the youthfull appearance of Ryan – he had more of the looks of a 16 year old than an 18 year old – made me wonder whether maybe he'd still have some growth left, for both his body and his dick. It also struck me how hard Ryan's dick was, sticking almost straight up, even though I doubted he was as aroused as he could get.

I noticed now how both Vince's dick and dickhead had the exact same color as the rest of his skin. In dick size he came in second after Joey, but he definitely had the biggest balls in the room. His sac provided ample space for his balls without hanging very low.

It was nice to watch how everyone had a different rhythm or style in jerking off. Ryan just used his right hand and concentrated on the top of his dick with mostly short strokes. Kyle was the only one who jacked of with just his left hand. Joey alternated between his left and right hand and used his other hand for support behind him as he leaned backwards. This pose also had the effect of aiming his dick more upwards. Vince slowly stroked the full length of his 7 inches while his left hand played with his impressive set of balls.

Looking at the four young hardons around me, I had to fight back the urge to touch them. I really wanted to jerk them all of myself, wanted to suck the cum out of them. Of course I couldn't, I had to control my desires as I knew even one attempt at actual physical contact would bring an immediate halt to an already very enjoyable moment. Take what you can get and be content with it, was going to be my motto here.

While I was stealthily trying to enjoy as much of the view as possible, I caught Joey watching at my dick. When he noticed I had seen him watching me, he turned just a little bit red and smiled, then returned his gaze to my dick for a while before breaking visual contact and closing his eyes. This confirmed my suspicion that had been growing throughout the evening that Joey was probably gay or had at least a keen interest in dick like I had.

In the meantime I had them all telling about their fantasies, as Ryan had done, which I found interesting to listen to and really hot at times as well. I learned that Joey loves the intimacy of a blowjob. Both Kyle and Vince had a big time crush on Kate. Vince admitted to fantasizing about a tit job from her. While sharing his fantasy, he started stroking his black cock more furiously. He was getting closer to his orgasm, and I decided to help him. Since they all shared a fantasy about a girl from school, I was trying to make them forget the fact that I never told them anything about my own desires.

"Can you imagine her laying here on the floor right now, naked, and ready for you to shoot your load all over her tits?"

Vince merely grunted an "Ooooh, yes", increased his jerking speed even more, before he almost completely stopped moving, just holding his cock firmly at the base, when he reached his peak. The day before I had already seen that he was a forceful shooter, and he confirmed that performance this time. Vince's orgasm was somewhat like a geyser. It started with a few very quick shots that came more like one stream, but without much force, followed by two very impressive spurts that almost reached Ryan on the other end of the circle. The next shots were almost as impressive in the beginning and then gradually lost force and speed.

The end of Vince's cumshot however was kind of lost on us since by then Kyle had reached his orgasm. He didn't shoot very far or very much. At first just a drop of very creamy cum appeared at the tip. Only right before I started to wonder whether that would be it, a thick jet came out landing only about 6 inches in front of him. The last two ropes of cum hung from his dick for several seconds before being thrown off by the motion of his stroking.

It looked like the quick succession of two orgasms was enough to bring Joey close to his. He had started to breathe more audible, and I knew he was there when his stomach started to contract. No more than two seconds later he started to release his load. Two violent spurts in rapid succession travelled across our circle, one of them partly landing on my dick. The three following bursts were more a spray than ropes of cum, landing a bit all over the place. A small shot seemed to signal the end of his orgasm, but was unexpectedly still followed by two more shots landing about a foot from his erupting dick. With a few more dribbles it then was really over.

Now, when Vince had started to cum, I had released my grip on my own dick and only softly stroked it since I didn't want to be too obvious about it. The point was to prevent myself from cumming to soon. I wanted to enjoy watching them cum before I finished off myself. However, the plan to wait till I was the last to go, went out of the window while I was watching Joey climax. It was so hot to watch, especially after I had already been stimulated by the sight of Vince and Kyle, I couldn't stop myself and just had to go to town furiously on my own cock.

It was only a matter of seconds after Joey came back to earth that I felt my cum rising from my balls to a violent explosion. Though caught up in the bliss of orgasm, I still tried to aim away from Ryan as much as possible. That meant that I head my dick pointed almost straight towards Joey when I started to unload. I figured that if the excitement of the evening would cause me to shoot way further than normal, Joey would much better be able to handle cum landing on him than Ryan would. It turned out to be an unnecessary precaution. I did shoot more cum and with greater force than usual, but not to that extend that it travelled all the way across.

That only left Ryan to go. I actually felt just a little sorry for him, because I had a feeling he didn't like it too much that all eyes were exclusively on him now. He had his eyes closed; his hand was more of a blur, in an attempt to get there as soon as possible. In the end he had a better orgasm than I expected from someone who seemed as reluctant about all this as Ryan. His cum started to dribble out in an almost continuous flow, several times interrupted by a shot that landed up to a foot and a half in front of him. While the force of his cumshot wasn't all that impressive after watching Vince's and Joey's, the amount of cum that he unloaded definitely was. When Ryan finished cumming, I was almost surprised that he still had his two balls after that.

We all started to dress in silence. Some of them were probably too awkward to speak, but I knew that I definitely wasn't the only one who was still revelling about the events that had just unfolded in this room. Before I left their room, I turned and told them: "Thank you, guys, it was fun. And at least, now we all have a reason to keep true to 'what happens in Italy, stays in Italy'."