Previously: Sam is spending the weekend with JT. After receiving his first enema, Sam is about to experience a couple of more "firsts."
"Jeff will be here in thirty minutes," JT announced. "He's coming over for a lesson in fucking. You're going to be his practice bottom. Come on."
JT led me to the living room where we spread a big bedsheet on the floor. It appeared that this would be the location of Jeff's "lesson" in fucking. Jeff was the upperclassman who had picked me up in his pickup truck, and had driven me home again, after my first night with the Hot Shots. I had performed oral sex on him that Friday night. I remembered how aggressive he had been, even causing me to gag at one point. I didn't really perform the oral sex; he more or less fucked my mouth.
"Okay," JT said, "get down on the floor. Your knees and your elbows should both be resting flat on the floor." I followed his directions and got down on the sheet. In that position, my ass was higher than any part of my body.
"You can even put your chest and head on the floor, if that would be more comfortable," Jim continued. He began to massage my butt cheeks gently. Then he gently spread them. He blew right onto my asshole, which felt so good and so cool and so sensual. Suddenly, I felt his tongue flickering against my hole. I howled with shock!
"Sir!?!" At first I thought it was some kind of an accident. My surprised reaction caused JT to use his mouth even more aggressively. What started as a light licking turned into gobbling with his entire mouth. His lips were kissing and applying suction. His tongue probed, licked, and slurped. I was shocked. I couldn't imagine anyone putting their mouth against anyone else's asshole. But I especially couldn't imagine a dominant Sir like JT doing that to his subordinate.
"Relax," JT said from behind me. "Your ass is as clean as your arms or your neck. We just spent nearly an hour getting our asses super clean. Try to enjoy it. Move into it. Your hole is like a mouth. Kiss me back." And he returned to what he had been doing with even more gusto.
I tried to do as he said, but I had no idea how to give a "kiss" with my asshole. I tried squeezing it a few times. I wriggled a little bit, and even moved slightly back and forth, pulling away from him and then pushing back into his face.
"Let's switch positions," JT said. I lifted myself up while he got down on his hands and knees. I crawled into position behind him.
"Is this new for you?" JT asked.
"Yes, Sir. It felt great. But I am still kind of shocked."
"You don't have to lick my asshole right now," JT stated. "But at least spread my ass cheeks and take a good close look."
I don't know what I was expecting. I had been fingered and fucked. But no one had ever gotten up close and personal with my asshole, nor had I ever looked closely at the anus of another human being.
I tentatively placed my hands on his butt cheeks, and slowly pulled them apart. I had heard jokes about the anus, and I had heard it called the "brown eye" or something. But now that I was looking closely, JT's asshole was a light pink color. The tissue kind of puckered up into the tiny hole. In a way, it did look like lips puckered for a kiss. And in a way, it did look like a rosebud. Had I heard it called a rosebud once before? I couldn't remember.
JT looked so good in this position. His svelte body was almost elegantly tapered. His trim waist made his shoulders look broad and handsome, while also making his butt cheeks looked round and snug. I experienced an unexpected jolt of lust, causing me to gasp.
We were interrupted by the doorbell. We got up off the floor and went to the door. JT checked the peephole to confirm that it was Jeff before we let him in. Jeff was dressed for summer vacation, wearing cutoffs and a crop top. That kind of clothing would look outrageously scanty today, but it was common in the late seventies. Jeff was very lanky. He had the hairy legs of a 30 year-old man, and his crop top displayed his magnificent treasure trail flowing from his navel down into his button-fly blue jean cutoffs. The physical energy that emanated from him was raw and primal.
He stepped into the living room where JT and I were both buck naked and boned up. He just grinned at us real big, and immediately started to get undressed. He dropped his shoes and clothes onto the floor in a pile without folding them. I thought again of JT's bedroom, and how all of JT's clothes were neatly put away. Jeff had a more carefree and messy manner which was sexy in its own way.
JT said, "Why don't you take a seat in that chair, and I'll have Sam get you warmed up." JT was politely inviting Jeff with a question, while simultaneously giving me an instruction. He was treating Jeff like a friend or peer, and treating me like a subordinate. I noticed the difference, but instead of feeling demeaned, I felt proud of JT's confidence in me. He and I were behaving as a team, and it was exhilarating.
Jeff sat down in an armchair, cocking one leg over the arm so that his legs were spread wide and his cock and balls were displayed and accessible. I got down on my knees and began to give him oral sex slowly and deliberately. His dick was semi-hard, and warm and slightly sweaty, but there was only a light whiff of odor. Instead of diving onto his cock, I started by licking his balls. He gave a small hoot of surprise and delight, and in seconds his cock was firm and pointing up to the ceiling. I was teasing his cock with upward licks when JT interrupted.
"Ass up, boy," JT commanded. "Doggie style." I managed to keep my mouth on Jeff while re-positioning myself.
I suddenly felt JT's mouth on my asshole again, and I struggled to maintain my composure. I had Jeff's cock in my mouth, and was trying to prevent my teeth from scraping his smooth, rubbery stick. I felt JT's finger against my hole, gently wriggling and pushing. In a matter of seconds, his finger was going in and out, firmly and gently spreading something slick and goopy.
Seconds later, I felt the head of his cock against my hole, and with a sudden thrust he entered me. I wanted to say, "Take what is yours, Master," but I could only moan while my mouth was filled with Jeff's penis. Jeff gave a moan of his own. The notion that two cocks were in me simultaneously was intoxicating.
"Easy, Sam," JT commanded. "Jeff's load isn't going in your mouth today, boy. It's going in your ass. Don't get carried away." JT was addressing me, but I think his words were also a message for Jeff to not shoot his load yet.
JT had us get re-positioned. I was on the sheet again, chest and forearms flat against the floor, ass high and wide open for business. JT got behind me with Jeff squatting next to him. JT entered me and withdrew several times, with Jeff watching. I was thankful for the enema, which made me confident that nothing gross or smelly was going to happen while my asshole was the center of so much attention.
Although I could not see it, JT had brought Vaseline and some rags. Although by this point I was thoroughly lubricated, JT made sure that Jeff coated his own penis before attempting to fuck me.
"First, just place your penis firmly against Sam's hole. Don't penetrate yet. Just sort of knock at the door." I felt Jeff doing exactly that.
"Now push a little bit harder," JT continued. "Don't force it. Sam will open up naturally and almost pull you in."
I don't think anyone could have had a better introduction to anal sex. Jeff got inside me at a nearly perfect angle, without experiencing any frustration or impatience, and without causing me any discomfort. Of course, JT had already gotten me fully prepped and relaxed and ready.
"Now you can go to town. Sam can handle it." Jeff started to pump cautiously. When he saw that I was okay, he started going faster and harder. His enthusiasm was contagious, even if he lacked expertise. At that point in my 14 year-old life, I knew very little about technique or expertise.
Pretty soon, he groaned a little bit, and suddenly he was coming. He banged as hard as he could as he climaxed, but he didn't hurt me. His force only pushed my chest harder against the carpeted floor.
A minute or two passed while Jeff caught his breath, and then he pulled out of me.
"That was wild," Jeff said. "Can I get a drink of water?"
Under JT's supervision, Sam has given Jeff his first taste of anal sex. For the first time, JT has put his boy at the service of another guy. Everyone experienced something new. The weekend isn't half over, and JT has a lot more to teach Sam.
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