A Higher Education (Can be Hard)

The audience erupted in applause as I ended my guest lecture at a college on how businesses doom themselves by not paying enough attention to gathering intelligence about what others are doing. Needless to say I got a lot of fresh numbers after that (dirty old man that I am!) And some of them were from really cute guys. As a 6 feet 1, 85 kg, buff, 40 year old top, I have a thing for skinny bottoms.

In the chit chat and mixing after the lecture one somewhat nerdy looking guy approached me. "Hi, my name is Lee and I really enjoyed your talk." I said "I'm happy you didn't fall asleep!" To which he laughed nervously. I got a real vibe from him and he was really shy and cute. He asked for my number as he wanted to do his project on business intelligence gathering. I was happy to share my contact with him.

By the next morning I found he had followed me or send a friend request on different social media. And we were Whatsapping and then Snapchatting. Old warhorse that I am enjoy, I do enjoy the excitement of these opening moves.

The advantage of being openly gay is that all of guys who are closeted or just shy feel safe in approaching you. And this was at play between Lee and I.

I let Lee set the pace because that is in my view very important. And after nearly a month of Snapchat he told me that he was gay and that he was still a virgin. He was too shy and college tops just didn't seem to do it for him.

Now I know how people love virgin and first-time stories. But its a big responsibility to actually deflower someone and be their first-time. That is one sexual experience they will never forget. And you are going to be a point of reference for a long time. And then there is the physical dimension. Bottoming for a real guy is not like anal masturbation. The dildo doesn't have a mind of its own and you can always stop if you lose your mood. For the bottom there is a chance he might get hurt if he hasn't prepared properly.

I also understand how it is better to have a first-time experience with an older and more experienced person who's secure about their own sexuality and knows their way around. So I told Lee that if he wants to get together we can. But we will take it nice and slow and I will take him through what he needs to do to prepare.

Lee was delighted at the prospect and we agreed to meet at my place on Saturday evening.

When my doorbell rang and I opened the door I found Lee smiling. He was wearing a turquoise T with dark grey jeans funny socks and sneakers. He was really slender and I felt a twinge of excitement just saying hi to him.

He came inside and we headed to the couch. I told him I had a movie set up and some snacks and drinks so we could relax first. He asked me a lot of questions about my life and work and growing up and I was happy to talk to him in person like this. What I loved about his questions is that he asked me how I felt about different things, not what I had done. I already knew this was a super-smart college senior and he'd have a great life ahead of him for sure.

I had laid out cushions on the floor by the couch and we settled in on them and I loaded the movie. By this time he had a drink or two in him so I felt he was more confident. As we got comfortable I asked him if it was okay if I held his hand. He nodded and I gently placed my hand over his. It really felt great. I have rough hands from working out and his were smooth.

I noticed a bulge in his pants. "Someone seems to be happy!" I pointed out as I now leaned over towards him, took his chin into my other hand, and gave him a soft my firm kiss on his lips. For a second he froze and then he relaxed and reciprocated. We must have made out for a long while because the movie was over half way through before we disengaged a bit. Kissing him was a pure delight - he was so submissive and warm. I really wanted this to escalate but I knew we had to take it real slow.

So I took my shirt off. He was mesmerised. He paused for a moment taking in my bulk and sheer physicality. Then he ran his hands over my pectoral and bicep muscle stretch marks. He felt my neck and shoulder muscles. And he ran his hand over my hard, flat, hairy stomach. He now took off his own shirt and climbed on top of me facing me and we resumed our make out session. His hairless, skinny smooth frame contrasted with my muscular, hairy, frame and we enjoyed the feel of each other's bodies. I kissed him on his nipples and sucked them causing him to moan in pleasure and he caressed my chest and neck while planting passionate kisses.

We both felt each other's bulges.

By now the movie was over and credits were rolling.

Lee whispered into my ear, "Please take me."

"Are you sure?"

"Yes." He replied.

I lifted him up in his straddle pose and we kept making out as I carried him to the bed room.

I lay him down on the bed and got fully naked before him.

My thick 6 inch banana dick was engorged and pulsating and he couldn't take his eyes off it. This was the first time he had seen a real cock other than his own. And this was also the first time that a cock was going to be going inside him for real.

I reached down and unzipped him and pulled down his pants and underwear leaving only his socks on. He had beautiful shaved legs, a small amount of hair on his pubes, and a nice 5 inch boy cock that stood to attention like a soldier.

I then turned him over onto his stomach. I pulled out a condom, wrapped my cock in it, and lubed up. I then moved to his butt and poured a generous amount of lube into his crack, rubbing it into his hole. He moaned from this massage and thanked me as he had never been touched there by a man (or anyone) before.

Once I felt his opening was well-oiled and warm, I told him I was going to enter him. Even with the lube this would hurt at first. If at any point he couldn't bear it he should tell me to stop and I would immediately do so. This wasn't a test it just a question of what he could take. No judgment.

I spread his cheeks, placed a pillow under his tummy to arch him a little. And then I got into position for entering him. I spread his ass cheeks and gently placed the head of my cock at his opening. I massaged his crack and opening with my cock letting him get used to the feel of a real cock on his hole and in his crack.

Then I began penetrating him. I pushed just the head of my cock in. He moaned loudly and winced. I let him adjust while telling him what a great pussy he had and how beautiful he was. He indicated to me after a few minutes that he was ready. So now I pushed deeper into him. This sent a wave of pain through him and I stopped once again, my cock about halfway in. He needed a bit of time to adjust. And then once he had adjusted I pushed the rest of the way in. He moaned very loudly and grabbed the sheets making a fist but he didn't ask me to stop or pull out. With a little more push my balls were resting against his ass and I was all in.

I leaned over him and kissed him on the neck and back of the head as I cupped his face with one arm. He kissed my bicep and slowly moved his ass away and back towards my cock in a gently rocking movement.

Lee was ready to be fucked.

I now pulled out and pushed in slowly giving him a feel for what a thrust would feel like. He smiled and moaned in pure pleasure now and this was the moment I had been waiting for. That point where the pain and anxiety of a first penetration turns into pleasure and a yearning for more.

I now fucked Lee at a steady pace enjoying his pleasure-laden moans and whimpering. He had a lovely boy pussy and it was my pleasure to inaugurate it. As we got more comfortable I increased my pace and I felt my orgasm building. I didn't stop and kept going till I came inside him filling up the condom. It was such a relief to unload after an extended romantic evening.

I turned Lee over after I came and kissed him before going down on him and sucking his cock. This was the first time oral experience for him too. I loved how his legs were trembling after the fucking he had just received. I gently pulled his shaft's skin down, took his cock head into my mouth and stroked and sucked. He soon rewarded me with a huge burst of cum in my mouth that I eagerly swallowed.

With that we lay in bed together cuddling. He used me as a big beefy pillow and I extended my arms around him. We didn't say anything. We just enjoyed the sound of each other's breath and heartbeat. I stroked the back of his head and enjoyed his warmth and touch. I didn't realise but we both dozed off for a little while. When we woke up it was late so I asked him to stay the night. He agreed and after cleaning up, I fixed us a light dinner and we snuggled in bed our spent cocks rubbing into each other as I cupped his butt and he rested his head on my chest.

The following morning he was sore and so we didn't have sex. Instead I took him out for breakfast and we had a great day together. He seemed a much more confident and relaxed version of himself. I was really happy that I had been able to shepherd him through such an important milestone.

We went out till he graduated and then he had to move for work. He still messages me now and then but I am really happy that he found a loving life partner and that they have a great life together.