It will come as no surprise that I could not wait until the next Saturday. For his part, Reese was cool about keeping his distance during sailing school. While we hadn't talked about why I felt uncomfortable him hanging around during the day, he had accepted that for whatever reason I didn't want us to be palling around at the school.
I wanted to explain my thinking about the students, but we didn't really talk at school and, except for Wednesday when we crewed for the dentists, we didn't socialize outside of school - that is except for the last couple Saturday nights and Sundays.
On Wednesday, when we did end up crewing, Reese was back to his usual friendly self so whatever he understood to be the reason for my coolness during the sailing program he had compartmentalized it to that. And this was great for me because I was once again the popular Chief Petty Officer that all the first and second year sailing students turned to for friendship and advice, and this in turn made the sailing instructors happy because it took a major load off their duties (young kids can be very demanding because of a lack of understanding and a need for affirmation).
After sailing on Wednesday, before I got in my mother's car, Reese said "we are still on for Saturday" as though this was a longstanding obligation. That was fine with me. I liked this obligation.
And on Saturday, it went pretty much like the week before. We spent the evening with his family, having dinner and then playing board games. We got ready for bed and after we watched TV and faked going to sleep, we ended-up putting our sleeping bags together, getting naked and he sucked me until I was about to cum in his mouth at which point I put his gorgeous hard thick cock in my mouth and gobbled down his thick load of cum while he drank down mine. Then, after him putting my briefs on me and getting back in his pjs, I fell asleep on my side with him behind me and his hand down the front my briefs playing with my cock.
In the morning I found our sleeping bags back where his mom had originally placed them, with no one the wiser, though this time no one came down to wake us, his sister simply shouted to us from the top of the stairs and we got up and joined his family for breakfast. This was followed by a family outing, this time to a pulp and paper mill (I was discovering that these outing were not just about family bonding but also were intended to be educational).
The following week was when things changed up a notch.
When I arrived at Reese's I discovered his parents weren't home. Like our first time, his sister was on a sleep over, his dad was at the hospital and his mother had some charity event. We were on our own.
As soon as I entered Reese locked the door, turned on the alarm and led me by the hand down into the basement.
Our sleeping bags were laid out as before. Though it was early.
Reese came up close to me and started to undress me. I moved to accommodate him, letting him remove my shirt, undo my belt, open my pants, push both my pants and underwear down and have me step out of them. He then had me lie down not in (or even on) a sleeping bag but on the floor between them. He then removed my socks so I was lying there totally naked.
As I lay there on the floor naked, Reese began to remove his clothes. This is the first time since strip-poker the lights were on and I was fascinated to watch. He removed his shirt, socks and pants. To my surprise he was wearing a jockstrap.
He turned around and modelled it for me.
"It's from school," he said. I had assumed that, though once he said it I began to realize that while it may be school issue for sports, this boy chose to wear this tonight with something in mind - what did he have in mind?
Whatever he had in mind the jockstrap looked awesome on him. His compact frame and square hips when he was facing me split nicely in the middle by the bright white of the wide jockstrap waistband. His big cock by any measure filled the pouch of that jock, and he was not hard, just filling them soft as he would in the locker-room at school. And when he turned his back to me, the leg straps and thick waistband framed the smoothest roundest firmest ass I had ever seen.
His ginger skin tone and smoothness made the jock stand out even more. Something about hips that are the same width as a torso framed in tight elastic jockstrap mesh take what was already a sexy stocky body and turn it into what you would expect to see in a fashion magazine in a sports team's locker-room photo-shoot. He may be 15, but his body in a jock was like a scale picture of a 19 year old football centre or running back.
My cock was rock hard as I lay naked in front of him and he clearly enjoyed my watching him model his jock.
Placing one foot on either side of my own feet, he dropped to his knees and leaned forward and whispered in my ear (his body so close I could feel the warmth he was radiating, his jockstrap clad crotch brushing every so lightly against my rock hard penis) "I want you to take my virginity."
I didn't know what to say. I had been fucked and it was not an easy thing. Did he know what he was proposing? And he called it virginity, which meant he saw this as much an emotional gift as he did a fun experiment (which is what is all I figured we had been doing up until then).
Before I could answer, he was up on his feet and was moving around, as if dancing, in his jockstrap above me. That smooth hairless ass framed by the white jockstrap was so enticing.
I was there for a sleepover. I expected we would have sucked each other off like we had a few times already. We knew each other's bodies now intimately. We were good friend. Best summer friends, as I spent the weekends at his place.
This felt right - though in the back of my mind something was screaming this was wrong. My being naked and hard and he wiggling his ass drowned out any noise coming from the back of mind.
"This is going to hurt the first time," I said. I know my first concern was it was going to hurt. My choice of words 'first time' was less clear. Was I suggesting we would do this often or was I downplaying that he saw this as his virginity and making it more casual about what everyone goes through as they experiment with sex (well those who decide to experiment with gay sex anyway).
Still shaking his hairless ass above me he said "under your sleeping bag, I found that in my parent's drawer."
I reached under the sleeping bag and found a tube of lubricant. I quickly blocked out of my mind that this was his parents' (though part of me wondered what he thought in finding it or even looking for it).
I put some on my cock and handed it to him.
He looked at me quizzically. He clearly had not thought through this even though he knew the basics and had gone to the trouble to search his parents' room for lube.
"Put some on your hole, and the more you work it into your hole, the less my cock will hurt going into your ass," I said.
He did as instructed and worked the lubricant into his hole.
"Try getting a couple fingers in there," I ventured, figuring it was better he work it in by himself, and loosen his ass up, than leave it to me and blame me when it hurt.
The other calculation I made was to stay on my back and let him sit on me.
"If you sit on my cock, you can control the speed. If it hurts, get off me, and only take as much as you can and then wait before you try anymore," I said.
"We are in no rush," I added when he looked unconvinced.
Positioning himself straddled on my hips, sort of like the first time when he gave me a massage, he aimed my hard cock at his hole and leaned back.
"Slowly," I said, as soon as he made contact with the head of my cock, as I could see the look of determination in his face.
Ignoring my advice, he pressed his weight into me and while the head slid nicely into his hole, it clearly sent sheering pain through him and he quickly pulled off of me.
Not knowing what to do to make the pain go away, I began to massage his inner thighs up and down (thinking that might take attention away from his ass) and playing with his cock and balls and stomach, trying to focus him on his horniness instead of the pain.
This had the unintended consequence of him trying again before he was ready. This time he got the head and about 1/3 of my cock into his ass, but from his face I could tell I was hurting him and I quickly grabbed him and pulled him off me and hugged him tight.
"Reese," I said, "you don't need to do this."
He looked at me like he was letting me down (there is something to be said for the lights being off during sex because that look broke my heart).
"Do you want to do it to me to see what it is like from the other side," I offered. Offered it probably not fair. In actually fact I would have loved to have his thick cock in me so framing it as my helping him was dishonest. It was probably short-sighted too because it elicited the defiant response "no, I can do this" (and once the words were out of my mouth I began to really really want him inside me).
From my experience, anal sex doesn't hurt when you turned on. Treating it like a challenge and bracing for pain usually leads to feeling pain (if you expect pain you will get it). But I let him continue. It was his show and I was just along for the ride
For the next few hours Reese would sit on my cock, take some of it into him, then tense-up and have to pull off. Each time he got more of it inside him, but each time he had to climb off me when the pain got too much.
I felt bad for him and whatever I said would not deter him from his goal. Though, to be fair, seeing him in his jockstrap straddle my cock and take some of it and even get off it and run around in pain was very hot. This boy in a jock was every man's dream (and I don't mean men who like boys, I was 17 and for me he was the perfect jock in a jockstrap who at that moment could have passed for a twenty something sport star). This boy was a perfect athlete with a compact body.
If we had been older and could have lived together, I would have him only wear a jock around the house as he filled it out so nicely and it framed his tight ass and accentuated his compact form.
Reese would rest in between sitting on my cock, and I tried to massage his ass and relax him during these rests, but that just made him want to try again.
Of course I was hard throughout this, as he alternated between running around in a jockstrap and then straddling me as his ass kept encasing the head of my cock and making me want more.
I lost track of time and suddenly we heard the alarm warning being engaged and we knew his parents were home.
I rolled into my sleeping bag, shoving my clothes under a chair, and he did the same, quickly turning off the lights.
Pretending to be asleep, we listened, hearing each other's panicked breathing louder than anything else as we had not only almost been caught fooling around, we had been trying something that was beyond what any parent would find acceptable.
We heard the door to the basement open and his mom say "I guess the boys are already asleep."
We lay there in silence and, if Reese was thinking like me, we were both trying to imagine what the noises meant in terms of when his parents would be going to bed. After what seemed like an eternity, I thought I heard light being turned off and I thought I heard his parents go upstairs to their room.
Then I heard Reese get up and, not sure what he was doing, I lay in bed silently wondering.
Eventually Reese came back and climbed into my sleeping bag and rolled me over so I was facing him, not away from him.
Rolling me over surprised me because I had figured he had given up on that ill-conceived idea of me fucking him and we were going to sleep as usual, with his hand on my crotch and him behind me. But he rolled so he was facing away from me, grabbed my arm and pulled it over his chest me, so I was behind him.
I instinctively wrapped my arms around him - he felt so natural in my arms. I hugged him close. Of course, not having cum and having been teased repeatedly by his ass, I was still rock hard. I didn't see that as meaning anything as I had gone to sleep the last couple Saturdays hard, it just meant I was content.
But as my hard cock began to press against his naked ass - well naked ass framed by his jockstrap - his hand went behind him and he took hold of it and aimed it against his hole.
I followed his guidance, though I had no greater expectation of success than him sitting on me, but I let him guide my cock to his hole and let him press against me. This time though I slid without much resistance.
I let Reese lead and he steadily pushed back against me and before long my cock was sliding all the way into his hole. I guessed when he got up and left, he had somehow stretched his hole, either with his fingers with lube or with something else. Whatever the case, he was fine taking my cock.
Before long I was all the way inside him. My arms had stayed wrapped around him from when I thought we were going to sleep and in this position, with my hilt buried deep in his asshole. I felt like we fit - his smaller body cradled in mine, my cock totally encased by his tight ass.
We stayed like that for a while. I could have stayed like that for the rest of the night. It felt so comfortable and natural. But I guess, once Reese got used to it, he became horny and wanted to be fucked because he started to move on my cock.
Responding in kind, I kept one arm around his chest and the other went to the front of his jockstrap. Interestingly he didn't push my hand away like he had when we sucked each other. I guess having a cock in his ass gave him the right combination of pain and pleasure that he knew when and how he wanted to cum.
As he thrust back I pushed forward. My hand on the pouch of his jockstrap didn't stroke him, but I did play with the pouch, as we began to fuck. He seemed more intent on fucking than me, I was doing my best to keep up with his shoving his ass down on my cock hard.
Before long he was pushing back with such force I thought he was going to push me out of the sleeping bag. I tried to push back in kind, realizing he wanted to impale himself on my cock, forcing himself to cum.
Unlike the slow steady movements that he had done with his head when he had sucked me, Reese was now frantic, trying to make himself cum by pounding his ass on my cock.
I held my body steady and pushed up when he needed me to, trying to help him make himself cum using my cock to get himself off.
I tried?.
The sensations were too much and before I could help myself I was cumming inside his ass. I grabbed him tight and told him "I am cumming" but that didn't stop him from pushing back as hard as he could again and again.
I shot a massive load into his tight (yes, I acknowledge up until then a virgin) ass. But he was not satisfied and he kept pounding, even as my cock started to go soft.
Once he realized I had gone soft, he was off me and kneeling with one knee on either side of my head feeding his thick cock into my mouth.
I was happy to take it, and before long he was up on his hands and toes, with his cock in my mouth, doing push-ups as he lowered his hard cock into my mouth and then pulled it out to the head and pushed it back down.
Instead of the steady methodical strokes, he was moving faster and faster and, as he fucked my mouth doing push-ups on my head, he began to cum. I swallowed as fast as I could.
After shooting four or five spurts down my throat, he leaned into me and left his cock deep in my throat as it unloaded the last of its jism. Once he was done, he lifted himself off of me and rolled over next to me and slid down.
Instead of curling up under my arm, he lay beside me and said "that was hot, thanks for taking my cheery."
While I had enjoyed everything about what had just happened, taking his cherry it was not. We had started by him innocently trying to take a cock in his virgin ass (something I was uncomfortable about with to start) but it ended with him using my cock and mouth to get himself off, which was not normal for him. Then again, I knew I was his one and only sexual experience so 'normal' may not be an appropriate evaluation.
I just knew that something between us had changed - then again I was unclear what it had been before it had changed.
I did know that I had had fun.
When I woke up in the morning the sleeping bags were in the same disarray as the night before and he was asleep next to me naked seemingly uncaring that someone could have come down and caught us.
Fortunately no one did, and while neither of us spoke of it, I suspected we both liked my fucking him in the ass and him fucking me in the mouth.
NOTE: Nifty needs donations to provide these stories. http://donate.nifty.org/donate.html