A Story From My Youth

We lay on the bed for a good while, my cock becoming soft inside the condom and our sweat cooling us down after such an unexpectedly perfect climax.

After a few minutes, I began to absentmindedly caress Pete's naked body. Over his hips and abs, pulling him closer to me now and again. I liked how my relaxing cock felt as it slipped against his body, surrounded by my cum.

He was clearly enjoying the sensation and after we had rested for some time he turned over - towards me - and slipped his leg between mine. I noticed then that he was clearly aroused again. His cock, very wet and lubed still (especially around his balls) pressed against my own softer cock as he grinded his hips into me. He wanted me to know how he felt.

I looked down. Smiled. I reached to rub our cocks together and gently slipped the condom off and let it drop to the floor. As I returned, I was pleased to feel that my cum had spilled and was now a pleasant lube for his hard rod.

He immediately moaned. He opened his eyes and began to speak, but stopped himself.

"What is it?" I asked.

"Well, I don't know...I really want to get off, the thought of you inside me is going to make me hard for weeks..."

"Mmm" I couldn't help smiling. He wasn't so confident now. Like a submissive, almost. I wanted to enjoy him as the confident, almost brash jock that had got us into this situation in the first place. "Okay, stud. I'll get you off. How do you want me to do it for you?"

He grinned. Pulled himself up, chest to chest now and eye to eye. "Do you ever take it...erm...well, you know. Can I..."

"Not if you ask like that" I teased.

"What?" he stammered.

"Look, if you want to fuck me, you need to ask for it. Just ask."

"Okay, then. I want to fuck you. I want to be inside you and pull your body onto me as I cum. How is that?" he tried.

I grinned and kissed him deeply. "I'll do anything you need, sexy."

I rolled onto him, making every effort to immediately line his cock up at my spread hole. He held his breath as he felt his cock head rub against my ass, between the cheeks and get stuck in the hollow of my opening.

"I'm going to need a little help..." I teased as I pushed onto him. "What did you use to relax your butt earlier?"

He blushed a little but only hesitated for a moment. He wriggled from under me to get to the bedside drawer. He pulled out a small back massager, bent upwards and with a small head. It was clearly used and unwashed and I wondered what the early afternoon had been like for him preparing for me coming.

I smiled and took it from him. I spotted more underwear in the drawer and so climbed off him to take a look. I took each pair out and graded them or asked him why he didn't pick the sexiest ones. He was clearly lacking the confidence to wear some of them when the time came to meet me. I told him that he'd chosen well, but that there was nothing to hide now.

I slipped into an electric blue jockstrap that he had - tight and smooth over my relaxed cock. I passed him a pair of silky red briefs that almost looked like panties. The waistband was very slim and they only came up to the base of his cock, exposing the pubes above. "Now they are brave" I said. "And so are you for arranging tonight. These are your trophy." I admired him in them as I lubed up my hole and the massager. I knelt on the end of the bed, watching him as I slipped the swollen head into my ass. It was petit, so felt fine on the way in. I let it settle in place, feeling tight but comfortable, as I leaned over him again.

His cock was filling his red briefs and I caressed it through the silk that was already tenting at my touch. His eyes closed immediately.

Slowly, I again teased his cock with my mouth, spending an age on the shaft and balls as the lube allowed the massager to begin feeling incredible inside me. Each time I needed to move for more stimulation, I exposed his cock more. Soon I was rotating my hips with gentle internal pleasure as I took his entire cock head into my mouth. I was trying to be patient, but all I could think of was getting him inside me.

I think he had forgotten about his request as he lay back and moaned with pleasure at every touch and movement. But, after around twenty minutes of slow and gentle touches I couldn't wait any longer. I knelt up. "Roll over and grab a condom, then. I want you inside me..."

He opened his eyes and seemed to hold his breath for an age. Then he smiled and slid out from under me to grab a condom from the drawer.

I watched as he rolled it on, his cock still standing out from the side of his briefs. "Shall I..." he motioned as he began to pull them down.

"Your call, stud. You need to fuck me exactly as you want me" I replied and arched my back to invite him onto me.

He slipped the briefs off and walked around the bed, climbing on behind me. I started to remove the massager and accidentally turned on a vibrate function. I twitched forwards in surprise.

"Oh...yeah, sorry. I didn't think to tell you it did that..." Pete began.

"Mmm" was all I could manage as my hips relaxed and returned my ass to his cock. The sensation of his cock head pressing the massager deeper into me was a perfect turn on. I wanted him now.

"Slip it out gently" I requested. "And lube us both up really well."

I lowered my upper body so that my hole was pointing up at him now. My head on a pillow and kneeling wide. I felt the massager slip backwards. Slowly. Gently. It was wet as it came out and I felt the gentle relief of having nothing inside me.

But his finger soon filled that space. He was treating me so tenderly. I loved the sensation and the hesitancy. I heard the wet, slipping sound as he lubed himself.

Eyes closed, I could only feel as he pressed the tip of his cock against my hole. I reached to guide him, pointing his cock downwards. He shifted his legs to give him more room and as soon as I felt the right angle, I pulled him into me.

He didn't respond at first and so I pulled again. This time he seemed to understand or feel ready himself, and so his cock head pressed harder at the perfect angle. The pleasure as he entered me is still hard to describe, but it made me moan out loud. "Oh...mmmm, Yeah Pete!"

His hands fell onto my hips and he caressed me as he pulled me onto his cock further. My insides burned and stretched, but the feeling around my hole made it irresistible.

Again, it must have taken another 10 minutes of gentle movements, re-tries and additional lube for him to find himself inside me fully and comfortably. He was careful to make sure I was ready for him and seemed to enjoy entering me each time.

I panted as he began to move more rhythmically. Feeling him push against my ass with his hips felt amazing and I just wanted more.

In time, I asked if I could swap positions, tired of holding my legs up. I knelt over him and leaned forwards as we kissed. Holding his cock, he entered me smoothly this time and he lay there grinning at me as I sat onto the full length of his shaft.

In time, he began to fuck me quicker from under me. Watching him stare into my eyes intently as his abs tensed at each push was all that I could take. His cock began to tease me inside and I could feel my soft cock weeping precum inside my jock.

By now he was groaning loudly and I could feel his cock become harder.

"Feels good?" I asked

"Oh, fuck yeah" he replied, as he held my hips. "I'm close..." was all he could manage between pants of breath.

I could feel that he was close by the speed and length of his drives into my wet hole. I leaned forwards and stopped my movements to allow him to control his climax.

He began, suddenly, to quicken the pace and begin to fuck me with shorter pushes. He stopped moaning and began letting out cries of pleasure.

"Ah...ah, yeah...ah...ah...yeaaaah..."

He suddenly pulled back and shuddered before calling "oh fuck, yes!" and immediately pushing back, deep into me. I could feel the pulses of his cock as he came inside me. The sensation was incredible and I realised that my own cock was now semi hard and wet.

I kissed him deeply as he drove into me on each new burst of cum. He was breathing through his nose as he tried to catch his breath, but never once pulled back from my passionate tongue inside his mouth.

It was a long time until we spoke. I relaxed onto him, feeling his cock relax within me. He lay there, looking at me silently with his hands on my hips still. His legs relaxed. I sat up, squeezing his semi hard cock inside me.

Slowly, we parted. Suddenly feeling tired and somewhat sore. We both commented on it. Sore cock heads and a gentle warmth in our butts.

After this intense experience, I remember feeling nervous that he would become awkward or want to rush off. But he didn't.

We lay together, eventually talking about all kinds of things. At first naked, then dressed in (less provocative) underwear. We spent all night talking, then slept together in the bed we had fucked in.

In the morning, after showering separately, we prepared to leave. All of the underwear got us talking and horny again and so we sucked and masturbated together until we came all over the bed. Laughing together, we kissed and cleaned ourselves up.

And then we left. I went back to University and he went home.

We met many times over the following year or two until I got a regular boyfriend. But Pete was always something special.