Making Up for Lost Time

Greg & Jeff
Story 2: Making Up for Lost Time
by Jeff Booth <jeffboy70@hotmail.com>
This story is a sequel to the story `Greg & Jeff Part 1: An Educational Experience'. If you haven't read that yet, please do so before reading this one.
In that story, my best friend Greg and I were caught smoking pot by the Headmaster, and were both caned as punishment. Afterwards, inspecting each other in the changerooms, we discovered a new side to our friendship...

That Wednesday was a momentous day for me. After Greg and I had left the changerooms, we made our ways home separately. Sitting uncomfortably on the bus, the marks of the cane still smarting on my buttocks, I tried to take stock of what had happened. As Dickens would say, it was the best of times; it was the worst of times. I had been caught for the first time in a serious breach of the school rules; I had narrowly avoided a suspension that would have been absolutely disastrous for my study; I had received my first caning in a manner that was at once both humiliating, painful, yet sexually stimulating. But most important of all, my love of my best friend had taken an unexpected but exhilarating turn when we had overcome our shyness and hugged, kissed and fondled each other to orgasm in a steamy, erotic shower.
What did this all mean? Two aspects were of particular interest. First, while awaiting my caning my penis had stiffened and remained erect even as the first blows fell. Was it just the stimulation of the wooden beam I was bent over against my penis, or did I really get off on this in true life, in the same way I had fantasised about? And secondly, Greg's behaviour in the shower, not only enthusiastically joining in our nude embrace but also, at the climax, spearing his finger into my anus to massage my prostate and ensure we would come together. Was this just the enthusiastic hormones of a horny young man, or did his feelings for me equal mine for him?
Both these questions would be answered soon...
Over the next two days, Greg and I did not really have time alone. I could have called him, but somehow, for the first time, I didn't know quite what I would say to him. "Hey man, that was some great sex, wanna go for it again?" Nah, not quite right. Let time take its course...
At lunchtime on Thursday, we were sitting with some other guys. The bell rang to summon us back to class, and Greg walked with me back towards the main building.
"Hey, how're you keeping?"
"Uh, still pretty sore."
"Me too. It was looking pretty bad this morning. Pretty intense, huh?"
"Um...." Now, exactly what was intense? "...Now that's an understatement!" I said, and shot him a slight grin. Let him interpret that how he wants...
"Would you like to come round and stay at the weekend? My folks are away and it's pretty quiet. I could do with some company."
My heart leapt. "Yeah, sure. I'm not doing anything. When should I come?"
"Come home with me after school tomorrow. Bring your stuff with you."
"OK, see you tomorrow."
A whole weekend alone with Greg. Normally, this would be no big deal, just a bit of fun. But given what had happened this week...

Thursday night was not a good one for me. I was as nervous as I'd ever been. I should have been relieved -- Greg was still talking to me, and even wanted to see me. I guess if he'd been freaked out by what happened yesterday, he wouldn't have invited me over so soon. As I stripped for bed, I stood before the full length mirror in my briefs looking back at the raised red weal that traversed the top of my thighs -- the so called "speedo stripe" that the Head deliberately applied on the thighs so that it could be seen when you were in your speedos or briefs. Hmm, still extremely obvious. I pushed down my underpants to reveal the remaining five stripes across my pale buttocks. Though not nearly as angry as they had looked yesterday, they were still very obvious, and tender to the touch.
I lay on my bed and masturbated, running my hands over my stripes as I stroked, eyes closed, imagining Greg was caressing me like he had yesterday. The orgasm came quite quickly and intensely, the warm semen pulsing onto my chest with a small drop hitting my chin. I cleaned up with an old towel. Normally, I fall asleep soon after coming, but tonight sleep did not come easily. I couldn't get my mind off Greg...

Friday was a day to be endured. The closure of the gym on Wednesday afternoon had been noticed by several people, and the word had spread that there had been a caning. No-one knew who the victim was. The secret wouldn't be kept for long, though. Greg & I had gym just after lunch.
Some smartalec noticed my speedo stripe as I was changing into my gym shorts. I was hoping it wouldn't be noticed until afterwards -- of course, there was no hope of concealing myself during the showers -- but no such luck. And Greg's was then noticed too. Nothing for it but to answer their questions, shortly and directly. What for? Smoking dope. How many? Six. Did it hurt? Of course. Those were the only real questions. There was a lot of laughing, a few jokers, and of course all through gym no-one could talk about anything else. Afterwards, we had to try to remain oblivious to the crowd as we dropped our underwear and wandered into the showers to rounds of applause and the occasional flicked towel snapping at our matching striped buttocks. I just concentrated and internalised it all, also trying to shut out the memories that being back in the showers might have raised if I had taken the slightest glance at Greg. I kept my eyes firmly on the wall and was out of the shower again quickly. Terribly embarrassing. At least we had the weekend to get over it.

"Thank goodness that week's over."
Greg & I had just sat down on the bus as it pulled away from opposite the school. Greg looked exhausted. I could just give him an "I agree" look and we both slumped back in our seats for the short trip to his place. We didn't need to chatter to each other -- we both needed a break to ease us into the weekend. It wasn't relaxing for me, however. I couldn't help but wonder what lay in store for us.
After we had ditched our bags and pulled off our jackets and ties, we settled down in his bedroom with a couple of drinks and some snacks.
We just chatted for a while about various stuff. It was Greg who broached the subject first.
"Gee, gym was tough."
"Yeah, but it's over. It's sort of a relief that everyone knows now. No more waiting."
"That's true, but it's not quite over yet. Tuesday afternoon?"
Oh shit. Swimming training. Damn. Our speedo stripes would be seen by the whole swim team. "Oh well, with luck they would have faded a bit by then, and everyone would know already anyway." Pause. "So how does it feel?"
Greg reached a hand down absentmindedly and rubbed his left buttock a little. "Still a bit sore, but more that sort of..."
"...Annoying feeling, a bit like those little itches?"
He laughed a little. "Well, now you put it like that..."
"Christ, it hurt at the time though."
"You're telling me. That fourth one..."
"You definitely lost out there. It was really harsh."
His hand went down to his bum and rubbed again. I decided to take a new tack.
"You know another way it's like those itches? You keep wanting to rub it. It doesn't make it better, but it feels good while you do it."
"Sure does," he said, after a pause. Our minds must have been both in the same place now, in the showers, afterwards...a moment's silence.
"Um, Greg?"
"Yeah?"
"When you got caned, did you, um...were you hard?"
He blushed a little and looked at his knees. "You must have seen that. I think you could have held a circus in my boxers."
"Uh, yeah, but that was before. I mean, after he started." Pause. "Cause I was, for a bit."
Pause. Then, more quietly -- "Yeah, me too. Not all the time though."
"Let me guess. The fourth?"
He nodded.
"Same for me. I guess you can only take so much pain."
"Yeah. But rubbing against that beam, it felt pretty..."
Pause again. We both had our hands down on our bums now, rubbing a little, thinking back to the time two days ago when we were bent over the beam, stripped to our underwear, legs splayed, with our semi-hard penises rubbing against the beam with each stroke. I felt myself firming a little. Time for me to make the next move. I swallowed.
"Have you ever thought about stuff like that?" There was no need to expand.
Very softly - "Yeah."
"Me too."
Pause. Then he said: "Have you ever..."
"Not apart from the other day. But I think about it a bit." (Pause.) "A lot actually."
"Same here. I've never...well, I've tried by myself a couple of times but..."
Oh, thank you God, I thought. I wouldn't ever have guessed. There was a long pause. I looked at him, he looked up at me from under his dangling fringe and bit his lower lip slightly. The silence continued. We both knew the next bit -- but it had to be said. Finally, after what seemed like an age...
"Would you like to try again together?"
His eyes said it all. His eyes, and the slightest of nods.

He reached out his hand to mine. We held hands for a little while, not saying anything. It was probably at that moment, more than any other, even more than our embrace in the shower, that we truly realised our special connection.
"Well, shall we ...?" I said after a few minutes.
We both stood up and ... yeah, well...what do we do now? We looked at each other and, realising the humour in the situation, giggled a little. "I tell you what. I'll go first," I said. Greg looked a little relieved. "Lets get a couple more pillows though."
Greg ducked off while I pulled the doona off his bed and folded it in the corner of his room. I put a pillow in the middle of his bed. He came back with two more - and a towel. Smart guy. We put the pillows in a little triangular pile in the middle, and Greg put the towel on top, "To keep them all together," he said (yeah, right).
We stood back for a moment and surveyed our construction. No use drawing it out any more. I kicked off my shoes. "Better test it out then." I got up on the bed and lay down over the pillows. My heart was pumping like mad as I gave them a bit of a punch to get them in just the right position. I settled down with my arms in front of me. It was a lot more comfortable than being over the beam the other day. I looked up at Greg and said "Why don't you get started on my trousers?"
Greg stepped up and cautiously put his left hand on my back, the right on my bottom. A thrill went through me as he rubbed my cheeks and I felt my penis stiffen. "You sure?" he asked.
"Yes please," I said, then added as I closed my eyes and my heart leaped into my throat "Please spank me, Greg."

The first few were nothing more than dull thuds. Even on my tender buttocks they didn't make much of an impression. There were a couple in the middle, then two on the left, two on the right. Pause. Four more, alternating between my cheeks. Pause. "How's that?"
"That's good...you can be a bit harder if you like."
The spanks started again, firmer, as I had requested. He would spank me about 10 times, then pause and run his hands over my back and bottom, occasionally giving me a little squeeze. It was not at all painful really, although my stripes had just started to throb a little, but feeling his hands on me was very erotic.
After about 30 spanks, during a pause I said "Can I take my uniform off now?"
"Yeah," he said, removing his hands.
I stood up and started unbuttoning my shirt. As I got to the bottom of the buttons, Greg gave me a quizzical look. Should I take mine off too? I tried to look noncommittal - Oh, if you want...- and he paused a moment before, I was glad to see, he started unbuttoning his too.
I took my shirt off, folded it on his table and unbuckled my grey school trousers. They fell to the floor and I folded them away too. I turned back just as Greg was removing his. I had put on a pair of my nicest tight white briefs for the occasion, and the swollen mound of my penis was pretty obvious. Because it was a gym day Greg was also wearing briefs, rather than the boxers he had had on the other day during his caning. They, too, were white, and also like me he had a noticeable erection. We looked at each other for a brief moment. I was tempted to give him a big hug there and then, but contented myself with reaching out a hand, rubbing it down his arm and saying "You look good." He blushed a little as I got back onto the bed.
He put a hand lightly on my back again, and this time I felt the warmth of his skin. His right hand touched my thighs, and ran along my speedo stripe. "Are they hurting?"
"Not really," I said.
He started patting my bottom again, then the first spanks. I am sure they weren't as hard as he had just been giving me, but I did give a little jump. The thick school trousers certainly made a lot of difference. There was more sting in his hand this time. He must have sensed me moving as he asked "That OK?"
"Yeah, keep going." I said.
He spanked me the same way as before, back and forth across my cheeks a few times, then taking a rest. After the first couple of sets he would start moving his hand down along my thighs to rub between them, brushing up against my testicles tucked away inside my briefs. This felt really good and I moaned a little, and spread my legs slightly wider, to show my appreciation. He spanked some more, harder this time, around the sides of my cheeks, and a few in the centre again. During the next break he slipped a few fingers under my waistband and I felt the thrill of his touch on my warming bottom. I wriggled my hips slightly in response.
A few more, and I was definitely starting to feel it. The next break came as quite a relief and he started rubbing my bum fairly firmly. "That's good" I said, and he obliged with a longer massage. As with after my caning, having my buttocks squeezed and rubbed did help to dull the feeling. As might be expected, the feeling from the spanking was quite different to that of the cane. There was a diffuse tingling all over my buttocks rather than the concentrated fire of the path of the cane, and the fact that Greg had been spanking to stimulate rather than punish meant the pain, such as it was, was far less intense. However, the blows awakened my stripes, which were gently throbbing.
A dozen more firm spanks. Then I felt Greg's fingers creep under the right legband of my briefs and slowly pull it back across my cheek, baring it. A slight touch on the freshly exposed skin, then the same treatment to my left cheek. His left hand, which had been stroking my back during this time, then came down, grasping the rear of my underpants and then tugging up sharply, pulling them deeply into the cleft between my buttocks. I gave a sharp moan as the fabric was pulled tight over my penis and testicles. "You like that, Jeff?" he asked as he started running his fingers over my exposed buttocks, tracing my stripes.
"Yes," I gasped. His touch on my bare bottom, coupled with the pressure on my genitals, was extremely stimulating. I could feel fluid seeping from my penis, moistening my underpants and scrotum.
He squeezed my cheeks a couple of times, then, still maintaining the tension on my briefs with his left hand, spanked me firmly twice across both buttocks forcing a startled "Ohhh" from my lips before he started slapping each buttock more lightly. The sting was much more acute than when my underpants had protected me, and after he delivered another hard spank to each cheek then removed his hand I could feel a definite warmth across my entire bottom. His right hand moved down to stroke my thighs and occasionally rub fingers across my cotton-clad testicles, causing my breathing to quicken.
Another round of blows, this time falling mostly around the sides and thighs. Then, after two firm slaps to each buttock, he released his hold on my briefs.
"OK Jeff, time to go bare."
My heart leapt. As he put his left hand on my hip I raised them from the pillows and brought my legs together. He slid a finger between the stretched legbands of my underpants, just below the waistband, and slid it slowly down to pull the material from my crack. His right hand moved to the waistband and he started slowly removing my final item of clothing. As they were drawn down I felt my penis straining as it was slowly uncovered, then springing free, shaft instantly stiffening into a rampant cock. Down past my thighs, then I lowered my midriff onto the pillows again to lift my knees and allow him to pull the briefs free. He put them down at the head of the bed, just in front of my face.
"Comfortable?" he asked.
"Yeah." My cock was now pointing straight up underneath me, with the fluffy towel and soft pillows underneath it. It felt nice. I had often arranged setups like this for masturbation sessions, humping pillows or doonas, and this only added to the eroticism of the experience.
"Hang on a sec," said Greg, and I glanced up to see him adjusting his own penis in his briefs so that it ran across the top of his thigh. He looked back at me and winked. God he looked sexy.
"OK man, get those legs spread nice and wide." I spread them, only to have him run his hand inside my thighs and tap them apart. "Wider...wider...looking good." My legs were spread very wide and I knew he could see not only my testicles but also the tight pucker of my anus. He ran a hand back and forth over my bottom, down to my thighs, and then between my legs to press up behind my scrotum. The feeling was fantastic and I started rubbing myself against the pillows a little, but stopped suddenly when he raised his hand and delivered eight hard and fast spanks, followed by two lighter ones per cheek, then two more firm ones. This definitely caused me to gasp a bit. He stopped and stroked hands lovingly and softly over my bum and back before delivering four more lighter strokes, two per cheek, and stroking me again.
Six more, then his hands started squeezing my ass providing some much-needed relief. I allowed myself to relax. However, I couldn't deny that my cheeks were getting quite painful. I knew I couldn't take this indefinitely. Another set, this time about a dozen, spread around, on the sides, inside thighs, and two at the end in the middle that hit my anus which was a totally unexpected feeling causing me to whimper a little.
"There, there" he said, stroking my back and patting my bottom a little before moving his hand down to rub my thighs, then slide between them to brush against my testicles then take them in his hand. I shuddered and moaned a little as he lightly handled my balls. His left hand started squeezing my buttocks one at a time. I was incredibly turned on and rolled around slightly.
Not for long though. He released my balls and they fell back to nestle against the towel while he delivered more spanks on my upper thighs, four more on my puckered hole, then some firm slaps to the cheeks that just kept on coming. I could feel the tears welling up and as he stopped I sobbed a little.
He laid a protective hand on my bottom. "Had enough?"
I was close, but not finished. "Give me a rest. Then one more set." He gently stroked me as I lay and composed myself. I waited about a minute for the sting to subside very slightly. An idea came into my head. I rolled it around mentally. I was scared but I knew I wanted it.
"Greg?"
"Yeah?"
"Can you -- can you get my belt from my pants?"
"Yeah, sure."
I watched as he walked over to where my school trousers were folded on his chest of drawers and fished out my black belt. His bum looked really cute in his white briefs, with his speedo-striped thighs running down in one direction and smooth bare back in the other. He turned around and walked back. He looked just as cute from front on, with his nipples hard and firm on his chest and a sparkle in his soulful eyes. His erection was still raging and his underpants were wet around his cockhead. He reached down absentmindedly and squeezed his balls a little.
"OK. For this last set please give me ten hard ones with your hand, then ten with the belt." He did his bite-the-lower-lip thing. "Yes, I'm sure."
"OK man, but say stop if you want."
I nodded then closed my eyes as he laid the belt down across my back. His left hand laid behind it and the right hand patted my bum. "Here we go."
The first was laid down hard in the middle of my crack, across my hole. Pause. One on each thigh, stinging my speedo stripe. Pause again. Then four hard ones, left, right, left right, in quick succession, followed immediately by another on my small pucker which stung hard and caused me to sob. A longer pause before the final two hand spanks, which were very hard on my left and right cheeks.
I was breathing deeply as he rubbed my cheeks and squeezed hard. It felt good instantly.
"Want to go on?" Greg asked softly. I knew I was pushing against my limit but I wanted to finish. I just nodded. He squeezed a bit more, then picked up the belt from my back, doubled it over and started sliding it over my nude body. Up my back, down and up each arm, and back and forth across my neck. Zigzagging down my back to my waist, then down across the left buttock to my leg. Lightly tapping the soles of my feet, then up my right leg to my buttocks once more. He drew it back and forth a couple of times and I clenched and unclenched my cheeks a little. He slid it down my crack, the cool leather brushing back and forth across my anus before continuing down to the insides of my thighs and my testicles. Broadening the loop slightly, he slid it under my scrotum then ran his hand down to draw the loop about my sac. I moaned.
"You want it, don't you?" he said, jiggling the belt up and down.
"Yes...yes please," I gasped.
He withdrew the loop from my scrotum and rubbed the belt over my bottom once more before lifting it up and bringing it down with a CRACK across both cheeks. The pain was sharp, sudden and concentrated. Still not as acute as the cane, but similar. CRACK again, in the same place, but slightly higher. It was sore but I could take it.
He shifted position slightly. One sharp stroke to the left buttock. One to the right. Then, the strap came down firmly along my crack, meeting my tender hole while the top of the loop curled down between my legs, narrowly missing my testicles but snapping at the sensitive and tender spot just behind my scrotum. An amazing wave of pleasure and pain shot through me and I cried out as the tears welled up.
"You OK?"
I nodded -- "Yeah...but watch my balls." Half way.
The next two were laid across the top of my thighs where my speedo stripe lay. A very tender area. I sobbed a little.
CRACK! Left buttock.
CRACK! Right buttock.
Then a pause before:
CRACK -- the final stroke, delivered forcefully across both cheeks.
And then it was over. I was sobbing with pain, pleasure, excitement, relief. Greg laid the belt down and placed his hands on my cheeks once more. "That was great," he said.
"Thank you," I sobbed.
"Thank you," he said, followed by: "Did you like that?"
"Very, very much," I said. That much was clear, I knew, from my throbbing cock, which had been rubbing between my stomach and the towel-covered pillows.
"Can I massage you?"
"Yes please."

Greg climbed up on the bed and knelt down behind my spread legs. He put his hands on my waist and started rubbing them up and down my back. I closed my eyes and relaxed. His touch drained away all my cares, running up through his arms. As he moved down and started rubbing my bottom, dulling the throbbing from the spanking he had just received, I felt myself giving in totally to him. His hands felt so safe.
"Your bum feels nice and warm," he whispered.
"'Cause you warmed it up so well," I whispered back. "I like you touching me."
He slid a hand down between my legs and brushed his fingers lightly across my balls. "Even there?"
"Especially there."
There was a pause as he took them in his hand and started lightly handling them. They rested on his fingers and he rolled first one, then the other, under his thumb. "I liked this in the shower the other day."
"I liked you holding me close," I said.
"What, like this?" he said, leaning forward and lying down along my body. He put his hands on my shoulders, gave them a little squeeze, and ran them up and down my biceps. I could feel his cock, still in his briefs, digging into my buttock. I wriggled a little under him. "Yeah, sort of like that." He ran his right hand down my side and began rubbing my thigh and ass while holding my shoulder in his left and lightly kissing my shoulder and the back of my neck. He began moving his crotch against my bum, giving it slow humps, and I moaned slightly. I started to roll my hips around too, grinding against the pillows.
"Hang on,", he said suddenly, and got up, stepping beside the bed once more. I heard him walk to his wardrobe and get something out. There was a slight squelch and then his hand was dabbing cream on my bottom and rubbing it in a bit. "This'll make it feel nicer." Another squelch -- it must have been a pump pack -- and my other cheek got the same treatment. He didn't rub the cream all the way in though.
His hand left my bottom again and there was the slightest of swishing sounds, before Greg's underpants landed on the bed in front of my face next to mine. "Don't want to get them any dirtier," he said. I thought it was cute that he kept making up these silly stories, as if he needed to conceal what we both knew. I heard another little squelch, and then the sound of cream being rubbed on, but not on me. Greg was lubing up his cock. I didn't look -- I wanted to feel it as it first touched me.
"Put your legs together," he said. I did so. He got back on the bed. This time his legs were astride mine. He leaned over me again, and as his weight bore down on me again I felt his slippery shaft sliding into position in my crack. Again he started running his hand down my side and stroking the back of my neck as he squeezed my thighs between his and started humping again.
I knew we were going for it this time, and I started rubbing back and forth underneath him as best I could, my cock rubbing around on the pillows. I loved the feel of his slick shaft slithering forward and back, tucked between my cheeks, his scrotum also rubbing around on my slippery mounds. His hand came up to the side of my chest, and I raised myself up on my elbows. He slipped his left arm under me and held me across my chest while his right hand came up to massage my nipples as he kissed my neck and shoulders. I gasped and moaned. I was very hard and pretty close.
His thrusting intensified and he started moaning and calling my name: "Jeff, Jeff, I want you so much..." I wriggled my hips more madly than ever, responding to his desire. I wished there was a mirror beside us so that I could see the sight, but instead I had to picture it...two teenagers in their prime, both naked, draped over a pyramid of pillows and humping madly, the bare wriggling buttocks of the boy on top beautifully pale and white next to his lightly tanned back and thighs, still marked from his recent caning...then I saw the boys as Greg and I, best friends, finding the ultimate pleasure in the touch of each other's nude bodies and caresses as we brought each other to orgasm. As the sheer eroticism of our situation dawned I felt my balls tightening. "Oh Greg..." I moaned as my buttocks clenched tight and started bucking up and down, pumping out my juices under my stomach.
He tightened his grip, squeezed his thighs tightly around mine and thrust up firmly and quickly against my quivering bottom. After about 12 strokes, just as my own spasms were dying, he let out an "Uhhh" and I felt the warm spurts jetting from his cock to trickle across my back.
I sank down and he lay, gasping, on top of me, his warm breath on my shoulders, the scented stickiness on my back and stomach, as we came down. After a short while he rolled off me to the side and, reaching down, I pulled out the pillows from under the towel so that we could lie flat on the bed together. I turned to him and looked properly into his face, still flushed and panting, as I hooked an arm and leg over his body and pulled him close. He reached up, ran a hand through my hair, then drew my head to his and we kissed, once, twice, then deeply.
"Oh Greg, it's taken so long..."
"...But it was worth the wait."
I reached down and took his right buttock in my hand, squeezing it, then running my fingers across the ridges of his stripes. "I guess we have a lot to thank the Head for."
His hand reached to my waist, pulling it in to him and squeezing first one cheek, then another. My bottom was still tingling from being spanked. "Still nice and warm," he said, kissing me again.
"Jeff, can you promise me something?"
"What?"
"Later tonight," he said, "after dinner -- promise you'll warm my bum up too?" And he gave me another squeeze.
"I promise," I said, and I drew him tight into a long, lingering kiss.

Let me know if you enjoyed the story or have any comments.