A Life Well Lived
I wanted to take the time to think back over the events of my life as they have transpired. I find the best way to do this is to write it down. If you choose to proceed further I hope you enjoy reading about my life as much as I have enjoyed living it. Firstly, it has been said that great comedy is born from tragedy. In my case you could say my life was likewise born of tragedy.
I have no clear memory of my parents, as they died together in a boating accident while spending a long weekend, a sort of mini second honeymoon. So at the age of four and a half or so, I wound up in the care of a guardian. He was my mother's first cousin and a man of considerable wealth. What I had come to learn was my mother was from a family of considerable resources but had decided to walk away from that.
Fate, however, seemed to have other plans, as least as far as I was concerned. So it was that I came to live in the spacious manor house of my `uncle' Nathan. He was a bit older than my mother and he tended toward a quiet demeanor and a subtle sense of humor. He also seemed to take the idea of being my guardian rather seriously. While the house had a handful of servants available he rarely left me alone in their care. Many times, when I wasn't in school, if he needed to be somewhere to deal with his various business interests, I was along for the ride. And sometimes those were long rides by plane.
I saw lots of things and met lots of people. It was fun. Then, shortly before the beginning of the summer at the end of my thirteenth year, I was informed that I was going to be spending the entire season at camp. I was dumbfounded and asked if I had done something wrong to make him send me away. He laughed a bit at this and pointed out that while I had learned many things at school and during our travels there was lots of other things to be learned and this was a way to do that. It was another adventure, but one that I should be doing on my own. Well, me and two hundred other kids.
So, two days after school ended for that year, I was standing at the edge of a large grass square among the aforementioned two hundred kids listening to the head counselor explaining how things worked and what we could expect for the next two months. Taken on its face, it did sound like there was a lot of fun to be had. Boats, swimming, sports, crafts, entertainment and a lot of nature. Then we received our assignments for accommodations, or billeting, as they called it.
Despite Uncle Nathan's money, this was not a super high end camp. It might have been considered in the top quarter of available programs so we were in shared rooms of four, grouped by gender and age. Two sets of bunkbeds per room with chests of drawers at each end for clothes. My roommates for the next couple of months were a bit of a mixed bag varying in height by about six inches, one a bit overweight and one of a mixed racial background. Introductions were made, hometowns identified and general interests for the summer discussed.
Then it was time for lunch. The first hint that things were going to get interesting came on the third evening after arrival. It had been a particularly hot, busy day and we hadn't had an opportunity to go swimming so it was mandatory that we hit the showers which in true camp style was a semi communal set up. Semi because it was separated by gender, one building for each on opposite sides of the green. The other was an age separation arrangement within the building. I naively thought this was to do with how the showers were set up.
Anyway, there was about a dozen of us in the shower room at that time and we did the usually dopey things that barely teens do at times like that. Throwing water, slinging suds and slapping asses. One of my room mates kept bumping into me, usually by backing up and bumping his wet ass against my leg. Something about it felt nice, odd, but nice. For no particular reason the next time he did it, I turned into him and pushed forward. This brought my stiffening erection into contact with his ass crease. He didn't make an effort to move.
I should note here that my room at home was more like a small version of a master suite. A spacious bedroom with a kick out area that held my desk and bookcase and a private bathroom that had a tub and separate shower stall. Sometime during my twelfth year I started getting erections and it wasn't long before I started using the shower stall as my own private masturbation chamber. Shooting hot loads against the glass seemed very exciting to me. So, here I was in a large shower room, sporting a very hard erection, pressed against the ass of a new friend.
But we were on a schedule and one of the counselors was yelling at us to finish up and clear out for the next shift. So we shuffled out to the adjacent chamber to dry off and get dressed. Andy, my roommate leaned over and said in low tones,
"Hang back as we're leaving."
I just nodded and slowed down and by the time I was ready to leave we were the last of our group to leave the shower building and the others were a number of paces ahead. He looked at me and said,
"Follow me."
While this was my first time at the camp, Andy was a multi-year veteran and knew his way around. Following behind I saw he was leading me into the trees directly behind the shower building. After about five minutes we were in amongst a clump of trees that had only a minimum of light.
"That felt nice in the shower. I guess you didn't mind my bumping into you."
"I guess, what was that all about?" I asked.
"Just this," he said, reaching out and placing his flat hand against the bulge in my shorts.
I jumped a little but didn't move away. I don't know if I was too shocked or too excited but I didn't have much of a chance to think about it.
"Wow, that feels like a good one."
Andy didn't even ask, he just grabbed my shorts with both hands and pulled down. Since the shorts were all I was wearing my erection bounced up and was practically sticking straight up. He gave me a look that had a brief smile and then a quick lick of his lips and then he was down on his knees in front of my, my hard cock in his hand and in quick order his lips were slipping over the head. It was at this point that my brain flashed bright and hot.
I had given myself some pretty hard orgasms but having a warm pair of wet lips sliding down the shaft was unlike anything I had felt before. Apparently Andy had done this before because he seemed pretty confident about how to go about it. Even now, all these years later I can remember how that first blowjob felt. He seemed to have been pretty impressed by my cock but it didn't stop him from getting the whole thing in his mouth.
I later came to understand this was called deep throating, or in this instance, deep mouthing, but having the whole thing in that warm wet place, coupled with suction and tonguing had me in a state of ecstasy. The next thing I noticed was the feel of his hands on my bare ass cheeks, urging me to push into his mouth so my hips started to move and picked up a rhythm that had me sliding my cock back and forth in his mouth.
After a while, one hand dropped from my ass and I didn't feel it anywhere else so I looked down and saw that his shorts were down and his hand was stroking his own cock. It was too dim to make out any details but he seemed to be enjoying himself immensely. I wish I could say this went on for hours but it was more like minutes. But they were magical minutes and then I was raising up on my toes and my hips bucked and I began shooting loads of cum into his mouth. He was very audible with his moaning and gulping.
Then he was grunting and his mouth came off my cock and he starting shooting his own load onto the ground at my feet. My head got light and my legs were rubbery and I had to reach out to lean against a nearby tree. Andy got to his feet and was wiping his mouth, grinning broadly.
"Damn, man, that was a real mouthful. You shoot a good load. You've got a real nice dick, too."
"Thanks. That felt really amazing. You surprised me, but I'm kinda glad you did."
And that was the start of the summer of my awakening. Sorry, I couldn't help myself. But damn did we have fun as you will see. When we got back to the room, the other two boys didn't seem to be interested in where we were. One of the boys pulled out a pack of cards and we spent the rest of the time until lights out playing poker. At least I think it was supposed to be poker. I don't think any of us really knew how to play.
Over the next few nights, Andy found ways to get us back to that secluded spot for repeat performances. Once I was over the initial shock, I looked for ways to be more of a participant. It was really fun when we faced each other with our pants at our ankles, stroking each other off. Andy showed me a neat trick where we stood close enough for him to get both cocks in one hand, squeezing them together, stroking until we both shot off, coating our cocks and his hand with cum.
The first Saturday night of the summer was celebrated with a big bonfire and sing along. If you paid attention you could see the occasional individual or couple fade into the flickering shadows amongst the trees. I looked over at Andy and he just nodded and went back to watching the antics around the fire. The festivities lasted until lights out and we all made our way back to our rooms.
The lights were out but one of the boys had a small electric lantern that he set on the floor in the middle of the room. The overweight boy, Joey, looked at Andy and said,
"So is the new kid broken in yet?"
Andy laughed a bit and said,
"Nice way to put it, Joey. But I think he's ready."
"Cool," Joey said and he started to peel off his clothes.
The other boy in the room, Will, turned around and with his back to us proceeded to strip down as well. Andy smiled and winked before following their lead. In a few moments all four of us were standing naked around the lantern. I was really familiar with Andy's body, but Joey and Will were new entities and I took the time to check them out. Will seemed to be a bit shy but maybe that was because he was self-conscious about what was starting to rise up from between his legs.
His skin was a tannish color but apparently it was concentrated in his cock because it was a dark brown and looking rather large on his slender frame. It was at this point the fun started. As if on cue, three arms moved to the person next to them and I quickly followed suit. It was my first circle jerk and it was a lot of fun. I was lucky because Will was to my right and I had an amazing handful.
It wasn't long before we were all at full hardness and it looked like I came in second to Will, but we were all hard and dripping and thoroughly enjoying ourselves. Andy looked at me and smiled.
"We started doing this last year. We were worried you might not, well, fit in. But it looks like we are in for a really fun summer."
I was happy to hear that and to show willing, I bent down and began to slide my mouth over Andy's cock. I was still jerking Will and Joey decided to join in by kneeling in front of me and slipping my cock into his mouth. This was going to be a fun night. It got really interesting when Joey and Will paired off and Joey began to messily suck on Will's big dick, getting it coated with saliva. Then Joey turned around and got on all fours, his bare ass pointing back at Will, who in turned knelt down behind the chubby boy with his cock in hand.
With one hand Will pushed an ass cheek aside and with the other he brought he head of his dick to the puckered ring and began rubbing it around. Then with a push, he began to work the head in. Joey grunted a bit but it was obvious he wanted what was coming and Will was more than happy to give it to him. I watched in fascination as Will finally got all of his dick into Joey's ass and began to rhythmically saw it back and forth. Joey lowered his head and shoulders until they were resting on the floor and his ass was held high. Will had Joey's hips held tightly and his pace began to increase and his hips began to make contact with Joey's broad ass with a slap.
"I hope you've been paying attention," Andy said, "because you get to do that to me now."
"Really?"
"Oh yeah, last year I got to really like getting my ass fucked. Let's get started."
With that, Andy gave me some of the same sloppy oral treatment to get me ready and then he too was on the floor with his ass raised high. Remembering what I saw Will doing I knelt down behind my new friend and since he was on the skinny side his asshole was readily accessible. So I took my slippery dick in hand and touched the head to the tight ring and tried to push in. There was some resistance but Andy wiggled his hips and pushed back so I kept pushing forward and after a few moments the ring began to relax and the head of my hard cock began to slide in.
Even at this early point the feelings that were starting to spread out from my balls felt electric. With a little bit more pressure his sphincter spread out and the head of my cock disappeared and a bit of the shaft followed. With this progress made, I took the opportunity to look sideways to where Will was pounding his cock into Joey's ass. Both were grunting and Will's head was flung back and his eyes were closed.
I took this for inspiration and added enough push to get my shaft moving and Andy began a low growling noise with his mouth pressed against his arm. With a firm grip on his hips I pushed and pulled back enough times to finally bottom out, my slim hips pressed against his ass, what there was of it. What there also was in abundance was a tight grip on the shaft of my dick and it was generating all manner of sensations that seemed to be gathering in my balls.
I wasn't really sure how much time had lapsed but at some point I heard Joey utter a muffled shout and looking over I could see his stiff cock was shooting streams of cum onto the floor. Within a few moments, Will began to jerk and push hard against Joey's ass and I assumed he was shooting his load into the boy's ass.
This was all I could take and with one more deep push I had my hips against his ass and my cock was spewing a hot, heavy load of cum into Andy's ass. At some point Andy joined in and began to pump his load onto the floor. When I was finally drained I couldn't help but slump forward onto Andy's back breathing heavily.
Anyone looking in, if the window hadn't been shuttered, would have seen four naked early teen boys laying on the floor and two puddles of cum. Thinking back on it now, with all that had gone on in that room over the course of that summer, if anyone had gotten even a part of it on film they would have made a fortune, provided they managed to avoid being arrested for child pornography.
As mentioned previously, this first time was indeed the first of many. Hardly a night went by that between lights out at ten and midnight we weren't engaged in some form of sexual adventuring. If boys could do it, we did it. Circle jerks, circle sucking, two ways, three ways and four ways were commonplace. It turned out we were all willing to fuck and be fucked. Andy was the first to take my ass and after the initial discomfort I found I really enjoyed having a hard cock buried balls deep in my ass. We were quite the crew that summer. And despite their availability, I didn't do anything with the girls other than be friends.
Between swimming, arts and crafts and some other activities there were quite a few opportunities but I wasn't particularly comfortable going beyond simple acquaintances and with all the sex available in my own room, why bother. An interesting diversion did occur about half way through the season when one of the senior counselors, a rather attractive college student who had a long history with the campground had mentioned that he thought I would make a good counselor and if I ever wanted to discuss it with him, he'd be happy to.
So, more out of curiosity than any real desire to pursue this, I met with him after dinner. As the campers had four to a room accommodations, the senior counselors had two to a room. At this time it was just him, and me of course. The discussion began innocuously enough, but as you might imagine it got more interesting and within half an hour of closing the door, I was standing in front of him with my pants down and my hard cock in his mouth. Apparently there was something of an underground information channel that identified likely lads, as we were called, and I came up on the radar screen.
Considering the fun I was having, I didn't really mind so much. And right now I was getting a very skilled blow job from a rather handsome guy who seemed to be really enjoying himself. His cock was about the same size as mine, which was interesting because he was at least six inches taller than I was. After about fifteen minutes of this treatment I made the suggestion that we get on his bed and suck each other off. He eagerly agreed. I guess he liked the idea I wasn't just going to be a passive load of cum in his mouth.
In fact, I got very active and while sucking his nice dick I began probing his ass with my finger and he replied in kind. Before I left that night, we each received a mouthful of the other's cum and then I dumped another load in his ass after a very hot fuck session. We had two more sessions before the end of the season, the last one including his roommate that had me spit roasted between them and finishing up with a three way frottage session that had us spraying cum on each other.
I'd also like to point out that while not available then, the advent of the Internet and social media, I've reconnected with a number of my camp friends. I love technology.
Of course all good things must come to an end and I found myself back home. This wasn't a bad thing, because home was a very good place to be. And with all of my experience, I was looking at things with a slightly different eye. For one thing, the chauffer that picked me up from the airport had only been with us since the beginning of the new year. From the back seat I noticed he tended to cast more than a few glances in the rear view mirror. Hmmmm.
As a way to test the waters, so to speak, I kept my attention on a spot somewhere out the side window of the car. Then I let my knees drift apart and my hand slide down so that I could rub the inside of my left thigh, which is where my cock was slowing making its way as things got more interesting. I didn't make any eye contact while the show was ongoing, but I did notice that the car jerked a couple of times as if the driver had been a little distracted. I should note that while he was called the chauffer, he did more than just drive, mostly because there wasn't enough driving to do to be full time.
Uncle Nathan had a handful of cars so they had to be maintained and other odd jobs fell into the job description. I had a feeling some other types of jobs were going to be added as well. It took a few weeks and in the meantime I did some more observing. The cook had been in our kitchen since before I arrived. She was in her early sixties, a big, rotund woman who apparently had a dozen or so grandchildren and made no attempt to interact beyond the needs of the kitchen.
There was a housekeeper/maid whose job it was to keep the rest of the house neat, clean and functional. Once a week two other women came in to help with the heavy work. The housekeeper was Miss Nancy to me and seemed friendly enough if a bit quiet, late thirties and reasonably attractive.
There was also a gardener and he was full time as there was significant acreage and all of it was put to some use. He was an older man, large, muscular and gruff. I tended to avoid him as much as possible. Even with my altered view of life, I wasn't likely to change my mind here. I got a good reception when I got home.
Uncle Nathan was happy to see me and I got a big hug and slap on the back and the usual questions about what did I learn and what kind of activities did I participate in. He also asked if I would consider going back and my response was an artificially reserved `yes'. I got a big hug from Miss Nancy who surprised me with the comment about how much she missed me around the house. She also commented that I looked like I had grown over the summer. And that I appeared more mature.
Dinner was quite an affair and it felt really good to be home. How good, I was soon to find out. Two days after getting home, Uncle Nathan left for a short trip to inspect a possible investment opportunity. It must have been something special because usually he relied on someone else's report to make a decision. So I was home with just the staff and I was looking forward to relaxing before the start of school.
On the first night, the cook made a really nice cake for dessert and I woke up around one in the morning with a desire for another piece. Now, I know the usual narrative would paint the cook as a tyrant who threatened dire consequences for anyone who invaded her territory. In my case, while it was true that I've had a stern finger wagged in my face on those few times I was actually caught, it was more a game than anything else. Besides she slept too soundly to be awakened at that hour of the morning.
So it was with some surprise that the kitchen light went on just as I closed the refrigerator door after returning the cake. It was more surprising that it was Miss Nancy that caught me. All she did was shake her head, put her finger to her lips and then pointed to the cake slice I had before me and gesture for me to follow. So I did.
I wound up in her room which was at the back of the manor on the first floor, as was the cook's, although further along. Once inside her room, Miss Nancy looked at me and said,
"You're growing up, but some things never change, eh?"
"Cook makes great cakes, I can't help myself."
"It's okay, dear. It's part of your charm. The charm of most boys your age. You're on the verge of manhood yet you still have the habits of your youth."
As she said this her hand came to rest on my leg nearest her, just above the knee. She gave it a squeeze as she encouraged me to eat my slice of the prize. At this point I should probably give a little detail of my relationship with Miss Nancy. She came to work at the manor after I had been there only a few months. I won't say she was like a second mother, but she was a confidant and someone I could talk to when I ran into things I didn't understand and didn't feel comfortable discussing with Uncle Nathan.
This was particularly true when it came to girls and how things unfolded over the last couple of years at school. She didn't try to brush it off with platitudes like `oh, it's just growing pains' or the like. She always tried to give me some insight into the lives of tween/teen girls and boys and how to navigate the potential pitfalls. At the moment however, the constant contact on my leg and the pulsating pressure was starting to cause reactions.
In fact, I was getting very aware of the fact that the head of my cock was starting to advance in the direction of her hand. If she moved that hand just a few inches further up, there was going to be some embarrassing contact. To be honest, I was of two minds about that. Scared how she might react and just a little excited about what might happen if she didn't mind. I soon found out.
By the time I was done with the cake her attention to my leg had me fully hard down the leg of my pajama shorts. She took the opportunity to use a finger of her free hand to wipe a little bit of icing from the corner of my mouth. As she licked her finger clean the other hand crept up my thigh and finally made contact with the tip of my cock and I flinched.
"Oh, my. You know I thought you were going to have something special, but I didn't know it would happen this soon. I hope you don't mind," she said as she shifted her hand so that it covered the majority of my bulge.
I just shook my head and let her do what she wanted. I was thinking maybe this was where I found out how the other half lived. Miss Nancy was smiling widely as her hand squeezed and rubbed my hard cock through the thin cloth of my shorts.
"Oh, dear, this feels so wonderful. So much more than I would have thought."
"You mean you've thought about my, you know..."
"Your cock, your nice thick, hard cock," she supplied, her eyes wide and bright. "You don't live under the same roof with someone for all these years and not find out some things about them. Why don't you let me pull these off so I can see what we have here."
Again, I didn't say anything, I just lifted up my hips and let her tug. Letting Andy guide me through my early adventures had worked out pretty well so I thought what the hell and went along with what was going on, or coming off. When my shorts were past my knees my cock was pointing straight up over my balls.
"Oooo, it's beautiful. Dear, you have a cock any man would be proud to have. Hmmm, let me see how this feels."
With that she reached out and wrapped her fingers around the swollen shaft. Then she began to lightly stroke. I could immediately feel that her technique was different than my roommates. Her grip was lighter and it was more a caress than a stroke. What came next surprised me more. As she slid her fingers over the smooth, warm skin she looked at me, locking eyes and then the next thing I knew her lips were on mine and I was getting my first kiss.
For whatever reason, none of the guys at camp wanted to do any kissing and I just thought that was the normal way of doing things. Miss Nancy showed me how much more fun it was to have a pair of hot lips on mine and someone else's tongue in my mouth. After a few minutes she broke off the kiss and looked at me from a few inches away. She had very pretty eyes.
"How did that feel, dear?"
"It was great, Miss Nancy."
"You know, dear, I think under the circumstances you could call me just Nancy."
I shook my head and in a moment of adult thinking said,
"You could never be `just' Nancy. Besides, I like saying Miss Nancy like this."
She gave me a big smile and then covered my mouth with hers again, tightening her grip on my cock, squeezing out a lot of precum. We kissed some more and then she dropped her mouth down until she was kissing the tip of my cock and licking up some precum. Again, it was a different feeling than with guys, not necessarily better, just different. This suggested that all sex wasn't the same and there were different experiences to be explored.
Right now, I was more than happy to let Miss Nancy use her amazing mouth on my cock and take what she wanted. And apparently what she wanted was to get my whole cock in her mouth. When she did she sealed her lips around the base of the shaft and began doing something with her throat that felt amazing. My hips started moving on their own and she put her hands on my bare thighs and kept working my cock.
As much as I would have liked this to last, between my great state of arousal and Miss Nancy's wonderful technique it was all too soon before my cock began to buzz and then my hips were bucking as shot after shot of thick cum spewed into her mouth. I could hear her gulping as she tried to swallow it all, but I could feel some dripping onto my leg so I assume she was falling behind. When my ass finally settled back onto the chair, she let my cock slide from her mouth. It was shiny clean and when I looked at her she was licking her lips and smiling.
"Oh, my dear, dear, boy. What a delicious load and there was so much. So lovely. I hope we can do this again."
I nodded vigorously.
"Oh, I'm so glad. Perhaps we can get an earlier start. I'd like to explore you more, but it's late and I have to be up and about early. So off you go and sleep well, my dear."
Wow. That's about all I could think at that point heading back to my room. One of my favorite people in the world had just had sex with me and said she wanted more. Like I said, wow. I spent a fair amount of time the next day outside. I didn't know if I was going to be able to avoid any behaviors that might prove embarrassing. Despite my busy summer, I didn't think that it `matured' me enough to avoid mistakes.
I was in my room by ten o'clock that night and it must have been around a half an hour later that I heard the door open and a familiar figure slipped in. Once again she put her finger to her mouth, even though the only other person in the house was one floor below and half the length of the house away. Miss Nancy came over and sat on the edge of the bed.
"Hello, dear. I just couldn't stay away. I hope you don't mind."
"No, I'm glad you came," I replied.
"Wonderful," she said, putting her hand on my leg which only had a sheet covering it.
She leaned forward and I managed to move forward a bit to meet her advance and we shared our first of many kisses that night. Her free hand took hold of one of mine and placed it on her bare leg. When our lips separated she sat back and her face looked a bit pensive.
"Dear, I need to tell you something. About myself. If you don't like what you find out, I'll leave. Okay?"
"Um, sure. I mean it's not like you're a serial killer, right?"
"No, dear. I'm not. But what I am is important to what we might wind up doing here. Perhaps it will help if I show you."
With that she slid her hand up to grasp my wrist and began to move the hand on her thigh further up, going up under the bottom of her brief robe. As my fingertips contacted the front of her panties, instead of the smooth flat surface I expected, there was a distinct bulge. My eyes popped wide and she was biting her lower lip. I, on the other hand, was getting even more excited.
I kept my hand moving until I was able to press it firmly against her bulge and I began to gently squeeze it.
"You're okay with this?" she asked.
"More than just okay. I sucked a lot of cock at camp this summer and I'll be more than happy to suck yours, Miss Nancy."
I was afraid the frankness of my response might put her off but the tension flowed out of her and the hand on my wrist pulled harder, getting my hand really tight against her panties. Her other hand moved from my thigh to my cock, still under the sheet but getting very visible. Then she was leaning forward hunting for my lips. We kissed again and while we did we worked on getting naked. Off came the sheet from the bed, then the robe from her body. I had my short pajamas on and she only had the panties. We made quick work of all that and then we had our naked bodies pressed against each other and she was in a frenzy trying to get as much tongue as she could in my mouth, while both our cocks ground together between us.
I had heard of transgenders or shemales or whatever you wanted to call them and I found the idea very intriguing and here I was in bed with one, who lived in the same house as I did, and who wanted to be having sex with me. How much luckier could I get? I had my arms around her back and my hands on her ass cheeks, pulling her tighter. She had a moderate sized pair of tits, implants I figured, but either way they felt really nice against my bare chest and her nipples felt really hard.
Then our mouths parted and she was looking down at me and she said,
"Oh, baby, I want your beautiful dick in my mouth."
"I want yours, too," I replied.
"Really?"
"Hell yeah."
Her smile was wide and a bit naughty and then she was sliding down my body, getting her mouth over my rock hard cock and then swinging her body around so that hers was within range of my mouth. Her cock wasn't as big as mine, but it was nicely formed and very hard. It reminded me of Andy's and we all know how well that turned out. I shifted a bit so that I could get my mouth to it and began to lick the head. Her precum had already started to flow and it tasted great.
I could feel her lips begin to envelope the head of my cock and I moaned, it felt so good. Then her hand was on my ass and she was pulling me deeper. I repaid the favor and with a single gulp got the whole thing in my mouth, my nose pressing into her ball sack. I grabbed a handful of ass and squeezed while I sucked hard. Now it was her turn to moan and the vibrations on my dick felt so good.
To this day I wish I had a recording of that first session with Miss Nancy. There were so many more to come, but that first time was magic. Two smooth, naked bodies, locked together, mouth to cock. The moans, the sucking and slurping sounds. One of the reasons I chose to write this all down was to give me a reason to recall it as much as I could. The sucking went on for long minutes, I don't really know how many, but finally I couldn't take it anymore, Miss Nancy really knew what she was doing and my hips began bucking and I gave Miss Nancy a major load of cum.
I guess she liked it because in just a moment she followed suit and her hips jerked and she proceeded to feed me a healthy load of cum. Hers tasted different than any of the guys I sucked at camp. I later found out that Miss Nancy was pretty much a vegetarian so I guess that might have had something to do with it. I managed to hold onto and swallow most of what she gave me, with just a little leaking down the shaft. Once I was done swallowing I licked the shaft clean and then I looked down along my body to see a similar action happening below my waist. Damn, what a turn on. Miss Nancy looked down at me and smiled when we made eye contact.
"Oh, my dear, lovely boy. That was so wonderful. It's been so long since I had someone do that for me."
"I'll be glad to do it whenever you want. Well, as long as we aren't in public."
She laughed and laid her head on my leg, still looking at me.
"So, my sexy young lover, what other things do you like to do?"
"Oh, I like jerking some ones dick while they do mine, grinding and stroking cocks together, and I really like fucking someones ass and them doing the same to mine."
"Oh, lover boy, all my favorites. Especially the last. Although I must say that I prefer being the bottom, but now and then I enjoy getting into a nice tight ass."
Her hand was running up and down my stomach and chest as she said this and it was obvious that in no way was my cock getting soft. She smiled as she focused on it and brought her hand to it, letting her short nails run down the underside of my cock shaft.
"You did such a wonderful job on my cock, baby boy. I would love to see how well you do with my ass. Are you ready for that?"
"Oh, yeah."
With that said, Miss Nancy rolled away from me and got up on her hands and knees and wiggled her ass in my direction. Her ass was slender like Andy's so her asshole was clearly visible and she made the sphincter flex and wink at me. My cock was still kind of wet from the sucking but I thought something more was needed and after a thought I hopped off the bed and ran to my bathroom, found the little bottle of lotion that I brought home from the last hotel Uncle Nathan and I had stayed at.
I brought it out with me and I got up on the bed again. Miss Nancy was now shoulders down, ass up and I took the bottle and let some lotion drip onto her tight ring. Then I added more to the head of my cock and placed it against her asshole. I heard her cooing so I closed the cap and dropped the bottle and took hold of her hips and began to push. There was a moment of resistance and then I watched as the head of my dick disappeared into her ass.
"Oh, fuck, that feels so wonderful. Keep going, baby boy, give it all to me."
So with practiced ease, I tightened my grip on her hips and pushed until the whole length of my dick slid out of sight. She grunted as my hips hit her ass and then I was fucking her. Slow deep strokes that had all kinds of signals rushing in and out of my balls. Then I heard,
"Faster, baby, harder. Fuck me hard and deep and fast."
So I did. With a firm hold on her slim hips I began to pound my cock into her asshole, watching as each contact spread up her back . Oddly enough, there was a narrow floor length mirror across the room and we were pointed in its direction. I could see her face as she lifted her head and her mouth was open and her eyes were half closed. Then they opened and I was staring into those warm brown eyes that had more than a hint of lust in them.
She reached back and took hold of one of my hands and I felt what a tight grip she had. Then it was the other and in quick order she was suspended from my arms like a bridge and her whole body was quaking to my rhythmic thrusts. Grunting filled the room and then Miss Nancy squealed and from the mirror image I saw her dick firing streams of cum out onto the bed spread.
That was enough for me and my balls began to unload through my cock into her ass and I just forced my hips against her ass and my body jerked with each stream. Finally, we both stopped and slowly, like some documentary about blowing down old buildings, we sagged sideways onto the bed, still joined by my cock in her ass and our interlocked hands. Once on our sides, we shifted a bit and I was able to snake my arms around her and we laid together like two spoons in a drawer.
After a period of heavy breathing I became aware that some warm wet lips were being pressed against one of my hands. I liked it. I also felt her ass squirming and grinding back against me. In a soft voice, she said,
"Oh, lover. I never thought the best sex in my life would be from my own dear boy. Thank you, thank you, thank you. You and I are going to have so much fun together. I don't want your fabulous cock to leave my ass. But I suppose we must."
"Do you have to leave right now?"
"No, sweetie, but I will have to go soon enough. I don't know when your uncle will be home in the morning and then there's cook. Besides, we have to clean up the mess I made of your bed spread."
So we stayed lying there, locked together for perhaps another half hour, her kissing my hand, me nibbling her ear until finally we rolled apart and with some effort, got ourselves off the bed. We cleaned up in the bathroom and then with a damp cloth, she blotted down the bedspread and then said she'd come back in the morning and put it in the laundry. With a last lingering kiss, with me still naked, she left the room. I crawled into bed and was asleep in minutes. It wasn't until I heard cook practically shouting over the intercom that my breakfast was ready that I dragged myself out of bed to start the day.
I was amazed. I was dragging around the house like I had just run a marathon, while every time I saw Miss Nancy she was going about her business happy as a clam. If she was sure no one was around she would wink or air kiss me. The next day school started and it was a new school. It was a private high school, boys and girls, and I resolved not to pursue any kind of relationships as I had all the sex I could handle and I was happy just making new friends and leaving it that way.
Miss Nancy was happy with this arrangement as she had full access to a horny fourteen year old with a nice big cock and according to her, wonderful instincts on what made my partner feel incredible. I had the same thoughts about her, but she also had years more experience.
Something new was added to the mix about two weeks after the start of school. I was dropped off and picked up every day by Clarence, the driver. I don't know why but I continued with my teasing, usually on the trip home.
Don't ask me why, chalk it up to temporary insanity or a teenager's hormone soaked brain, which I guess adds up to the same thing, one Friday afternoon I pushed things. It was a warm day so my jacket was off and I decided to undue my belt and pants so that I could pull my semi hard cock out and begin stroking it. I could see by his expression that the driver was way surprised but very interested. I found out just how interested when, after coming through the gate onto the property, he pulled into a small grove of trees.
He stopped the car but kept it running and then climbed out, only to climb into the back seat next to me. In short order, he had his cock out and was stroking it up to full hardness. When we were both fully erect I could see he had a nice fat one, not as long as mine but definitely a meaty handful. If on a cue, we let go of our cocks and switched hands so that we were stroking each other off. It felt so cool. I had done this plenty of times at camp but it was a lot more exciting to be with a grown man in the back of a car just off the driveway of my uncle's property.
We went on like this for perhaps a quarter of an hour before I heard him grunt and then his hips started shoving upwards and he began to shoot. His first two shots went up about six inches and dropped back onto his cock and my hand, with the rest oozing out. But he oozed a lot and by the time he was done, my hand looked like a glazed donut. All that cum was a huge turn on and I started shooting my own load which went higher, had more shots and it landed on the seat, my legs, and his hand and arm.
Clarence reached into a compartment on the back of the driver's seat and pulled out a cleaning cloth and some wipes and made quick work of the mess. With a brief smile he got himself back behind the wheel and backed us back onto the driveway and drove me the rest of the way to the house. I headed for my room in a very relaxed state of mind. During the course of the school year we had a few more instances, well, like maybe every other week. Always just the hand job and never a word was spoken. It was great fun in a unique kind of way.
Miss Nancy was a guest in my room at least three times a week. At least two of those times had me giving her ass a thorough fucking that had her cumming hard. Mutual oral with both our mouths getting filled with cum was also a staple. Miss Nancy was also good at introducing me to new experiences, like sex in my shower stall. Or taking a bath together and playing with each other in a lot of soapy water.
One special occasion was the first night she decided she needed to get her dick in my ass. I had been waiting for this moment but I didn't want to push since she was having so much fun with me fucking her. On this particular occasion, we started with our usual mutual jerking and sucking and then she told me that she had to have my ass. I told her anytime she wanted. Her growled answer was `now'.
So I rolled over onto my hands and knees, and looked back over my shoulder. She got on her knees between my legs and she spread my ass and dipped her head down until I felt her tongue begin to dance around my tight ring. Damn, that felt good. For the next ten minutes or so, she was licking and spitting and getting my ass ready. I even felt her tongue push past the ring to enter my hole. Then she was ready to get down to business.
I don't know where she pulled it from but a bottle of gel lube appeared. She squirted some on my asshole and rubbed it in with her finger, pushing in a little to start opening me up. Then she had the head of her cock against my hole and I felt her start to push in. I kept looking back at her because I liked how her face looked when she was really turned on. That I was the reason for such passion was pretty damned amazing.
When she was balls deep in my ass I let my head come to rest on the mattress, giving myself up to her and letting her call the shots. Her technique was different than mine and showed me a few new tricks. One was to double push at the bottom and every few strokes to drive hard and then wiggle her hips. Then she leaned her chest on my back and reached around to grab my dick and stroke while her hips short stroked my ass.
I was in heaven. And I didn't want her to stop, and I said so, a number of times. As she fucked and stroked me, she was kissing my back and whispering to me about how I was her sexy lover boy and nothing felt better than my ass wrapped around her cock and she and I were going to be fucking each other forever. I liked that idea.
I also liked the idea when she had me flip over onto my back so she could continue to fuck me with my dick squeezed between us and she lying flat on my body, her mouth on mine and her tongue trying to find my tonsils. My hands were gripping tight to her ass and I added extra impetus to her hip thrusts.
Then she was growling into my mouth and her hips were pegged to mine and she was dumping her load of cum into my ass. That was all I could take and I began to push up hard with my hips and a massive load of cum was being pumped up between us. When she was finished she just slumped on top of me, her head next to mine, her lips nibbling on my ear. I wrapped my arms around her and decided I didn't ever want to let go.
The fact that we fell asleep that way sort of felt like we would stay like that. In the early morning hours I felt the bed move but I didn't respond and went back to sleep.
My freshman year turned out to be a ton of fun. School was school but I did well with studies, did some clubs but stayed away from sports. I really didn't like the idea of getting beat up and wearing myself out for my other physical activities.
The summer that followed was equally fun. I was back at camp and back with my buddies and the sex started up the first night back and kept going all summer long. I seemed to attract the attention of a few more senior counselors so I assume that they traded info on likely playmates. I was more than happy because two of the older guys had really nice, big cocks to play with and some things for me to learn. Even a few of the girl campers were giving me the eye but again I wasn't ready to deal with all that so I just stayed friendly and it was a smooth season of fun.
Returning to school for my sophomore year life became more complicated. That was when I met Stephanie. She was a freshman and to this day, she was the smartest person I have ever met. She was also the quietest and most reserved. It was still my intention to not engage any of my classmates beyond friendship as I was getting all the sex I needed at home and I had already seen how complicated things could become by observing how some of those classmates interacted.
Stephanie was a unique experience. In addition to being so intelligent, she was also a very pretty girl. Her eyes were hazel with a touch of green. They looked a bit overlarge for her face which made it look like she was constantly astonished by the world around her. Her hair was a golden blonde that was moderately wavy and hung halfway down her back. She was half a head shorter than I was and on the slim side.
We met the first day of school as we had the same class. It was supposedly an advanced math class for sophomores, but Steph was allowed in due to her previous work in classes in middle school. She probably should have been on a face track to college but her parents were concerned that her shyness would put her in awkward situations among students that much older.
We had our first real conversation the following day at lunch, were she, amazingly, sought me out with questions about the school. I found out quite a while later that the reason she came to me was it seemed I was the only boy she saw that hadn't been eyeing her up. In all honesty, I had to admit that I was, I guess I just did it with more subtly.
You had to concentrate when you talked to Steph. She talked so quietly and she tended to not look at you when she did. But as the school year went on, the things we talked about were so interesting you couldn't help but want to try harder to listen. Any number of times I found myself almost head to head to hear what she was saying. Damn, this girl was not only smart but her view of the world was so next level it amazed me.
We wound up spending a great deal of time together working on homework and school projects, talking about this or that and on a number of weekends her parents would drop her off with her bicycle and we would ride around the manor grounds checking out this or that. She had a real interest in all the plants and flowers and things. My guess was she'd be studying botany or some such when she got to college. It turned out I was only partly right.
Uncle Nathan threw me a curveball that summer between sophomore and junior year. Instead of camp, I wound up working as his `assistant' tagging along on local and long distance business trips so I could start learning about all the various enterprises he was involved in. At first it was a depressing idea, missing out on all that fun at camp. Of course, I'd have Miss Nanny and even the driver to play with but what I didn't realize was the opportunity for fun on the road.
Unfortunately, Steph was going to be gone almost all summer on some sort of enrichment program. Fortunately we both had phones so talking and texting was a daily occurrence.
It was funny how many horny guys can be found in major hotels. Yeah, yeah, I was still pretty naïve in those days. My first fun came when Uncle Nathan and I wound up in the same hotel as that being used by several contestants of a national stage band contest. I was doing some laps in the pool one afternoon when Uncle Nathan was tied up in a confidential meeting. I was just floating around when I saw a boy come into the pool area. He appeared to be Asian and was kind of on the small side. He was also wearing a speedo, something they didn't allow at camp. He looked pretty hot. When he saw me he waved and then ran and jumped into the pool. He surfaced about six feet from me, spraying water.
"Hi."
"Hello," I replied.
"You here for the band competition?"
"No, I'm here with my uncle. He's taking me around to show me his businesses."
"Ah, cool. If you were from a competing band I wouldn't be able to talk to you," he said, rolling his eyes.
"You aren't supposed to be rehearsing?" I asked, knowing nothing about how a band operates.
"We've been doing that yesterday and all morning today. Now we have the afternoon off, the competition starts tomorrow."
"Cool," I said and then splashed some water at him.
That set off a splash fight and then he ducked down and swam towards the other side of the pool. I followed along on the surface and by the time I got to the side he was up and hanging on the side of the pool. Up close I could see that he was a pretty cute kid. I was a little surprised when I felt a foot brush up against my leg but I guess maybe the Speedo should have been a clue. This was followed by a gentle nudge to my crotch with his knee.
"Here?"
"Not exactly. Come on," he said and then he pulled himself up out of the pool.
I got a quick glimpse and saw a bulge in the front of his suit. My board shorts were getting pretty bulgy themselves so I clambered out of the pool and hurried after. He had a cute little ass that flexed inside his suit. He led me to a door that when opened led to a room with supplies and stuff. He closed the door and then looked at me and said,
"We don't have much time."
Then he was on his knees in front of me and tugging on my wet swimsuit. When it slipped down past my knees he let out a gasp then said,
"Holy shit, your cock is massive, man."
By the time I was ready to enter junior year I was around five eight and my cock had reached a thick eight inches. Miss Nancy had commented often how big I was getting and how lucky she was. I kept thinking I was the lucky one. Oh, well, win-win, I guess. Anyway, my little friend had both hands on my cock and he was licking the head and then plunging his mouth down over it.
His technique was aggressive and a bit frantic. I wonder if he was used to getting his fun in quick burst like this. It was still fun and he had me super hard and wet in moments. I joined in by putting my hands on his head and doing a little face fucking. That seemed to get him more turned on and looking down I could see he had his suit to his knees and he was using one hand to jerk a smallish but nice looking cock.
Since he seemed to like the way things were going I kept it up, giving him a good fucking. He used his free hand to grab my bare ass and pull me in further and I got the idea he was trying to get the whole fat thing in his mouth. Unfortunately, his gag reflex was getting in the way but it also meant I was getting a really nice blowjob in very exciting circumstances.
It finally got to the point where my balls were pulling up tight and then with a bit of hip bucking, I began to unload my cock into his mouth and throat. He responded with some strangled gurgling and his own convulsions as his cock shot some pretty decent streams of cum that hit my legs and feet.
When he was finished gulping and sputtering, he looked up at me with a big grin and said,
"Damn, that was a big hot load, thanks. I gotta get going. Maybe I'll see you around again but if not, this has been a cock to remember," the last being said with a tight squeeze of my deflating dick.
Then he was up on his feet, tugging up his speedo. He dashed out to the pool, jumped in to rinse off and then he was out and on his way to his room, I supposed. I took a quick dip as well and then grabbed my towel and headed back to our room. Uncle Nathan still wasn't back so I took a quick hot shower and had a nap before dinner.
Over the course of that summer, I found some fun in a few more hotels. The most noteworthy for its uniqueness was my encounter with a middle aged former bodybuilder, the most massive human being I've ever encountered. He managed to convince me to come back to his room with him, which admittedly didn't take much talking. I was fascinated by the idea of seeing him naked.
The first surprise was his actually deepthroating my whole cock and using his tongue to lick my balls at the same time. He kept at it until I shot my first load directly down his throat. It was an amazing experience. Then we got into the shower together and he had me oil up his entire body and then using my oily hands to jerk his cock and finger his ass until he exploded a nice load all over the glass door. For the grand finale he leaned on the vanity and I used my oiled up cock to fuck his oiled up ass. We were practically the same height so getting my dick inside him wasn't much of an issue.
It was amazing to see my fat cock sliding between his rock hard ass cheeks while they glistened from the overhead lights. I also got to see a lot of his broad, even expansive, back and all the muscles that rippled as I fucked forward and he pushed backward. When it finally got to be too much and I began pumping another heavy load of cum up his ass, he went over the edge and his asshole clamped down hard on my shaft and he started bucking, shooting his load onto the vanity counter top.
So, all in all, that summer wasn't a bad one. Uncle Nathan and I travelled a fair bit, I saw a lot of new places and got a really good idea of his far flung interests. I got the idea that he was worth a lot more than even the manor house indicated and it was apparent he wanted me to be intimately involved in it all someday.
As I said, I had some interesting sexual exploits along with my usual with Miss Nancy and occasional backseat hand jobs with the driver. But, like all the others it came to an end and I found myself back at school. It was great to see Steph again and get caught up. Yes, we could talk and text but there was still a lot to be discussed face to face, and what a face.
Her hair was getting longer and her face was maturing a bit more and all in all, she was turning into quiet the stunner. But she was still so quiet and reserved, so when after lunch that first day she asked me to take a quick walk outside with her. It seemed she was walking closer and even seemed to be pushing up against my side a bit, although it did help hear her talk more about her summer.
We wound up in a corner of a courtyard where a large ornamental shrubbery blocked all but the most direct view. She turned to face me and wonder of wonders she looked me straight in the eye and said,
"If I ask you a direct, personal question, will you give me an honest answer?"
"Of course, as long as that answer wouldn't hurt someone somehow."
She nodded and smiled a bit and then asked, simply,
"Are you gay?"
The question surprised me but then again, not really, considering what I allowed people to see of me. So, taking a breath, I said,
"I suppose I can understand why you'd ask, but no, I don't think so. But for the sake of full disclosure (yes, I was learning a few things listening to Uncle Nathan), the only sex I've ever had has been with other guys."
She blinked a bit and then asked,
"Why is that?"
"To be honest, it's just easier. With the other guys, it was just for the fun of it. We were friends and it was a fun thing to do. It just seemed that with girls it would be more complicated and I didn't think I was old enough, mature enough, to deal with it properly. Considering some of the things I've seen and heard about here at school and at camp, I think I'm right."
"So, do you think you're old enough now?"
"I don't know, are you hoping that I am?" I asked, thinking I knew where this might be going.
Then she really surprised me when she closed the distance between us, grabbed a handful of my blazer and pulled me down so she could get her lips on mine. Several thoughts raced through my head. One, this was a really important milestone. Second, this was a huge step for Steph and my reaction was going to be equally huge. Last, her lips felt really good and this was an incredible turn on. So, marshalling all that Miss Nancy taught me, I took hold of the arm that she was holding me with, pulled her harder against me and returned her kiss with vigor. I even parted my lips, which she mimicked and then our tongues were lightly touching.
Her free hand came up and got a grip on my free arm and the kiss got more energetic. One interesting aspect of our first kiss was that Steph didn't moan as such. It was more like a purr and I found it very sexy. When we finally pulled our mouths off each other, her eyes were boring into mine. Her expression was questioning and I thought I knew what the question was. So I said,
"Nope, definitely not gay."
And then I kissed her and it went on for a few more minutes and then it was time to get back into school mode. But now school mode meant walking together as closely as we could get away with and when we had our heads close to talk she was much more likely to be making eye contact and if a table was involved, our knees were touching. On those occasions when Steph came to cycle around the grounds we would find ourselves sitting under a tree, doing some serious making out.
It turns out my quiet, super intelligent friend was a passionate young lady who's friendship for me had flamed into some pretty serious feelings. She said something pretty surprising one day as we were resting from some biking and some heavy making out.
"What you said before about you having sex with other guys, that was really true, wasn't it?"
She was saying this while lying stretched out with her head resting on my thigh. I looked down at her and said,
"Yes, you asked for an honest answer and that's what I gave you."
She pursed her lips and then said,
"If this is something that you do with friends, I don't mind you still doing it. I think I'd be upset if you did it with another girl though. Does that sound strange to you?"
I was a little surprised that she chose this time to bring it up, but like I've said, she saw things from some unique points of view and she has asked some odd questions at unusual times before.
"I think you're making the distinction between messing around with friends and expressing feelings for a person, probably with a deep emotional connection. That's not all that strange."
"I'm glad you understand that. I have to admit that I find this all rather strange for me. I was very happy with being friends and it was all going so smoothly, and then school ended and we were going to be apart for the summer and it felt so horrible. The idea that I wouldn't see you every day at school and being here on weekends was so depressing. It was about two weeks into the program and one of the facilitators asked me why I seemed so down. When I told her, she smiled at me and said it sounded like I was in love."
I looked down at her and she was looking back up at me, her big eyes seeking something and her cheeks looking a bit rosy.
"Are you?"
"I don't know, I've never been in this situation before," she said matter-of-factly.
"To be honest, neither have I. I guess we'll just have to find out together."